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The Grand Tour of New England

15 days, 14 nights

If time allows and it is your first visit to New England, a self driving road trip tour covering all six New England states will allow you a true taste of the region and all of its beauty and diversity. After leaving Boston, you will find wide open spaces, a friendly and hospitable welcome, and wonderful accommodations. Your hosts and innkeepers will serve as local sightseeing guides pointing you toward those perfect places to enjoy the scenic beauty of New England.

                                                       Explore More Road Trips & Itineraries

Day 1 — Boston, Massachusetts

Most international visitors arrive in New England at Boston’s Logan Airport . Conveniently located just three miles from downtown, Logan’s international terminal allows for a speedy transfer through customs and immigration and into the city. There are a variety of ways to get into the center of Boston , including public bus, subway and taxi.

Remember not to rent a car until you are heading out of the city — you will not need a car in America's “Walking City” and parking fees downtown are particularly expensive. Most rental car companies will allow for downtown pick up or failing that, the short journey back to Logan Airport is worth it on your day of departure from the city. Boston is the capital of Massachusetts and the unofficial capital of New England. A sophisticated and charming city, it is relatively small and walking is the best way to get around. Many international visitors feel very comfortable in Boston as it is the most 'European' of all American cities, with distinct small neighborhoods such as the North End , filled with lively Italian restaurants and cafes; the Back Bay, where wonderful shopping streets are filled with every designer shop imaginable; and Beacon Hill, with its cobbled streets and brown brick townhouses. Spend at least two nights in Boston to get the best feel for the city.

Places to stay in Boston

Day 2 — Boston

Spend the day exploring Boston’s unique history and locale. Here are some ideas to get you started:

• Walk the Freedom Trail.  A great way to easily see a lot of the city, the Freedom Trail links 16 places of historic interest throughout the city. You can begin anywhere along the route, but it is easiest to begin at Boston Common where the Visitor Center is located.
• Take A Duck Tour. The "Ducks" are amphibious vehicles that are able to travel both in water and on land. Boston Duck Tours  offer a wonderful perspective of Boston and Cambridge: see the skyline from the Charles River and hear about the unique sights of the city from your Boston driver!
• Other great ways to see the city include Trolley Tours , which allow you to hop on and off the trolley, or a cruise on Boston's beautiful harbor .
• Tour Fenway Park. Fenway is America’s oldest baseball park, home of the iconic Green Monster. Tours of Fenway Park are offered year-round, and if you visit during baseball season (April to September), you can also catch a Red Sox game.
• Consider putting aside some time to visit some of Boston's rich cultural gems, such as the JFK Library , the impressive Museum of Fine Arts , and a favorite for kids, the New England Aquarium .

Day 3 — Boston to the Maine Coast

Leave Boston today to begin your road trip and head north up the coast and into Maine . Time allowing, you should stop and visit any one of the wonderful small towns on the coast . Salem, Mass. , is known for the infamous Salem Witch Trials and is home to the amazing Peabody Essex Museum , whose collections include art and cultural artifacts from all over the world. A little farther north is the pretty artist colony of Rockport. A helpful note: most highways in New England have speed limits of 55-65 miles per hour (90-105 km/h).

The rugged state of Maine is as big as all the other New England states put together; on this tour, you will explore a little of its spectacular coast. Picturesque fishing villages are nestled together along a dramatic coastline. Don't forget to sample some of Maine's fine culinary delights — lobsters and blueberries! You may prefer to stay in the southern coastal areas, in the beautiful coastal towns of York, Kennebunkport, and Ogunquit, or continue north to Portland, a lively port town with a rich historic and cultural heritage and a budding culinary scene.

Search for accommodations in: Portland, Maine • Ogunquit • York • Kennebunkport

Day 4 — The Maine Coast

Spend the day exploring the coast of Maine: a visit to Portland with its many small galleries, shops, restaurants and museums, is a treat for city-lovers. Maine’s smaller, coastal beach towns are especially popular for their family-friendly sandy beaches, fresh seafood and relaxed atmosphere. For a quintessential Maine experience, take a lobster boat ride from Perkins Cove in Ogunquit, or stop by one of the many lighthouses along the coast, such as the Nubble Light in York or the Portland Head Light . Many fine small museums that scatter the coast, like the Wells Auto Museum and the Ogunquit Museum of American Art . Freeport, Maine, is also a good day’s stop for outlet shopping in a beautiful New England village.

Day 5 — Maine to the White Mountains of New Hampshire

Today, drive west through Maine and into New Hampshire's White Mountains region .  The drive will be longer today as there are no major highways to take you east-west in this part of New England. In New Hampshire, beautiful shimmering lakes and high mountains dominate the landscape, as the road winds through pretty villages. A paradise for hikers in the summer and a playground for skiers in the winter , the scenic White Mountains provide the perfect backdrop for outdoor recreation or quieter relaxation. A day of traveling can end on a high note with a trip to the top of Mount Washington , the tallest mountain in New England (6,289 ft / 1,917 m). In the summer, you can get to the summit on foot, by car on the 8-mile toll roador via the Cog Railway on a steam train. In the winter, the auto road can still be traveled, but only on a snowcoach tour.

Day 6 — New Hampshire

Spend the day exploring northern New Hampshire . A wonderful tour for driving follows the Kancamagus Highway between Lincoln and Conway, one of the most scenic in the USA. It also offers a chance to visit the Flume , a natural granite gorge with wooden walkways and rushing waterfalls. If souvenir shopping is on your list, New Hampshire is also tax-free and North Conway is one of the premium outlet shopping areas in the region. You can also travel a little further south into the Lakes Region of New Hampshire . Lake Winnipesaukee, the largest lake, offers everything from great sailing and fishing to relaxing water cruises on paddleboats.

Find lodging in New Hampshire

Day 7 — into vermont's green mountains.

Continuing the tour westwards, Vermont is the next stop. The Green Mountain State is known for its pristine landscape, rolling hills and the romance of small communities where white church spires poke up between the mountains. There are many lovely places to stay in Vermont, and you can choose to stay in the northern , central or southern part of the state. You will have the opportunity to experience the twisting country roads, mountain views, small towns, art galleries, country stores, locally-grown food and working farms throughout the state. One suggested stop in Vermont is the the state capital city, Montpelier. It is the smallest state capital in the country with just 8,000 residents. The town looks like one you might have seen in the movies, and is dominated by the gold-leafed dome of the Vermont State House. Continue on to Waterbury and take a unique factory tour at the Ben & Jerry's Ice Cream Factory and then onto Stowe , a charming mountain resort town nestled at the foot of Mount Mansfield.

Day 8 — Vermont

On your first full day in Vermont, make time for a visit to Burlington , Vermont's largest city. Many points in town offer beautiful views of Lake Champlain and the Adirondack Mountains in New York. Burlington’s large student population gives it a great "buzz" — nightlife, restaurants and music halls are busy year-round. A pedestrian-only shopping street, Church Street , is the heart of the city with a mix of local and high-end boutiques, restaurants and bars. Burlington is also an ideal place to sample some of Vermont’s famous craft beer. Spend the night in Burlington, or get a head start on the next day’s travel by heading south. Route 100, the “Skier’s Highway,” winds down the spine of the Green Mountains, past ski resorts, lakes, and gorgeous views, with plenty of opportunity to stop for the night in quaint Vermont towns.

Find places to stay in Vermont

Day 9 — Vermont to The Berkshires, Massachusetts

From Vermont, head south and into the lovely Berkshire Mountains of western Massachusetts . Charming Stockbridge is the heart of a region packed with culture and charm. In summer, the hills are a hot spot for musical talent, as the Tanglewood Music Center becomes home to the Boston Symphony Orchestra. Summer theater and dance performances are abundant, as is cutting-edge modern art at Mass MoCA and fine art at the world-class Clark Institute in the lovely college town of Williamstown.

Search for lodging in the Berkshires

Day 10 — to connecticut.

Continue your journey southwards and into Connecticut . Stretching east from New York City, Connecticut’s varied landscape includes wooded hills, rural farmland, rocky shores, and wide beaches. Many areas have beautifully preserved clapboard homes set amidst well maintained villages like Essex and Chester .

Travel south until you hit the coast of Connecticut, where there are many small towns that are worth exploring. Mystic is a good choice for a stop. Visit the Mystic Seaport , a living history village with working craftsmen, the world-class Mystic Aquarium or the Mashantucket Pequot Museum , which depicts Native American life in southern New England.

Search lodging in Connecticut

Day 11 — newport, rhode island.

A must on any visit to New England, Newport is as famous for its seaport history and Gilded Age mansions as its superb summer festivals. The cliff top mansions are truly magnificent homes, many built by the wealthy industrialists of the nineteenth century as a place to escape the summer heat of New York City. Beautifully preserved, you can tour 11 of these historic homes from different periods in American history. Save time to stroll along the Cliff Walk , with great views of the ocean, or to enjoy the downtown fun of Newport.

Places to stay in Newport, Rhode Island

Days 12-14 — cape cod, massachusetts.

A perfect way to end your visit to New England is to stay for a few days on beautiful Cape Cod . Base yourself in any one of the charming small towns and villages along the Cape and enjoy spectacular beaches, museums, music festivals, antique stores, sailing, great golf courses, and whale watching. Spend a couple of days in Cape Cod, enjoying the beaches, sun and sand on the high dunes and long beaches of the National Seashore . You can also explore the small towns and villages of Cape Cod, characterized by beautiful clapboard architecture, faded to a dusky grey from salty air. From spring until autumn, you can take a whale watching boat tour from many parts of New England — the feeding grounds for the humpback and finback whales are found just 30 miles (50 km) off the Massachusetts and New Hampshire coasts. These magnificent creatures played a huge role in New England's history: the whaling industry flourished here. Today, whales are protected but the history of whaling in New England can be seen at several area museums. A day trip to Martha's Vineyard or Nantucket is an option as well — ferries to the islands run year-round, though passages are more frequent in the summer months. The best way to explore the beautiful island landscapes is on a bike. Nantucket Town is a sight to see, thanks to its Georgian houses, old-fashioned street lights and brick pavements. Martha's Vineyard is closer to mainland Cape Cod, and a little larger, with several distinct and interesting towns. Both islands have great shopping, lovely sights, and the freshest seafood you can get.

Find lodging in Cape Cod, Martha's Vineyard and Nantucket

Day 14 — Cape Cod & Plymouth

History enthusiasts, don't leave New England without a trip to Plymouth, Massachusetts, and the Plimoth Patuxet (formerly the Plimoth Plantation). Plymouth is where the first Pilgrims settled back in 1620 after first landing in Provincetown. Plimoth Patuxet is a recreated Pilgrim settlement, where costumed interpreters work, eat and speak as the 17th-century colonists did while Native Americans demonstrate traditional methods of building homes and canoes.

Day 15 — Boston for Departure

Cape Cod is approximately a two hour's drive from Boston (depending on your exact location on the Cape), so depending on your flights, you may want to relax on the beaches of the Cape this morning or start the day in Boston. After a grand tour of this size, a leisurely morning is just the ticket.

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

READ NEXT   18 Magical New England Christmas Towns that are Straight Out of a Hallmark Movie (Updated 2023)

Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  November 8, 2022

The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options!) 2024

Having traveled through the entire New England region for 15+ years, I’ve been able to get a strong understanding on the best things to do, and I’m so thrilled that I’ve finally developed my ultimate 7 Day New England Itinerary to share with you!

A 7-day itinerary to tour New England has been one of my most requested topics, and I totally understand why. It’s so hard to look at a region comprised of 6 gorgeous states, and try to figure out what’s worth your time, and what you can leave out. Well, good news – I’m taking the guess work out for you. In all my years of traveling through this region, I’ve cherry-picked what I think is the best route to take to plan the perfect road trip in 7 days.

While I think everything is pretty much worth your time in New England (I’m a bit biased!), this itinerary focuses on the best of the best, and also takes into consideration efficiency so you have as much time as possible to also enjoy your destinations.

This itinerary is also geared toward those who are visiting New England for the first time. With that, let’s get into it, shall we?

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

How Many Days Do You Need In New England?

You can easily spend anywhere from a few days to a month in New England, so this entirely depends on how much time you really have to dedicate to your trip. This post will prove that you can easily see some of the best things in this region with my 7 Day New England road trip itinerary.

But, that said, more is always more when it comes to time to travel, right? 😉 So of course, you can easily turn this itinerary into a 10-day adventure, or even two weeks. Under my 10 Day New England road trip itinerary option later in the post, you’ll see that I’ve made notes on side excursions where you can easily add in a day or two to extend your trip even further.

And of course, you can definitely see some of the best places in just 5 days, and I’ve included a 5-Day option at the very end for those who don’t have as much time (and don’t worry, it’s still pretty great!).

My motto is always, “Even if I just have one day, it’s better than not going at all,” so whatever time you have for your trip with definitely be worth it. I’m excited to cheer you on as you plan your trip 😊

Where To Start A 7 Day New England Road Trip Itinerary?

For any road trip through this region, Boston is the best place to start, especially if you’re flying in. Boston Logan International Airport typically offers the cheapest flights to this area, and is also a worthy destination to explore on its own.

Not only that, this city also incredibly convenient to most places in New England, and is centrally-located in the region, and therefore, is just the easiest starting point. For that reason, pretty much all of my itineraries on this website start in Boston because after years of experience, I’ve found this to be the absolute best option.

If you’re not flying in, however, and already live in this area, or are driving in from nearby, Boston is still a great starting point ( especially if you’ve never been!). But you can definitely adjust this itinerary to start from anywhere in New England that best suits your needs.

The only time I would suggest using a place like Portland, Maine as your starting point if if you plan to really only explore the northern areas of New England, like the rest of Maine or New Hampshire. But even in that case, Boston is still just as convenient, so it will then simply depend on personal preference at that point.

7 Day New England Road Trip Overview

Day 1: Boston – New England’s biggest and most exciting city!

Day 2: Woodstock – Vermont’s most beautiful town.

Day 2 Alternative Option : Skip Woodstock, and stay an extra day in Boston, with a day trip to Salem if you’d like.

Day 3: The White Mountains in New Hampshire – Home to breathtaking mountain views, and New England’s highest peak.

Days 4-5: Bar Harbor and Acadia National Park – One of the most charming coastal towns in New England, and the spectacular views in the park make this destination worthy of two nights.

Day 6: Drive to Portland, Maine , with optional stops along the way.

Day 6 Alternative Option : Stay the night in a smaller coastal town if that’s more your speed!

Day 7: Head back to Boston , with some great stops along the way.

Notes About This Itinerary

→ For some stops along this route, I also suggest other options to really help you create the ultimate road trip for you based on your preferences. So keep an eye out for those, and get ready to take some notes!

→ This 7 Day New England road trip itinerary also follows a true road trip style , meaning you’ll be in a different town each night of your stay (with one exception, which is Bar Harbor). You can certainly tweak that to your liking if you prefer to stay in one place for two or more nights – do what feels right for you.

→ Lastly, this itinerary was intended to show you around all the different landscapes New England has to offer, so I wanted to include a mix of urban, countryside, mountains and coastal to show you the very best of it all. I also focused on locations that are largely perfect to visit year-round, so seasonality was not factored in.

Day 1: Boston

Boston is one of my all-time favorite cities, and as mentioned, it’s the absolute best place to start your road trip – especially if you’re flying in. I love that it feels like an exciting city, but is also incredibly charming, historic and packed with character. There’s just something very cozy about it, and it’s most definitely worth spending a day exploring during your 7 day New England road trip.

An alternative option, depending on how tired you’ll be once you arrive, is to tack Boston on at the very end. In this case, you’ll want to immediately depart for Woodstock once you arrive, and then spend your last day in Boston (but follow this itinerary for everything else in order).

Here are some awesome things to consider doing on your day in Boston:

• Walk the Freedom Trail: this group tour is an excellent choice!
• Meander through my two favorite neighborhoods: Beacon Hill & the North End.
• Stroll along the waterfront areas – the Charles Esplanade is especially beautiful.
• Walk through the Public Gardens – the bridge is such a great spot for gorgeous photos.
• Eat, eat, and then eat some more. The culinary scene in Boston is incredible, and seafood here is a specialty.
• In fact, take a food tour for the inside scoop on all the best places: here are my favorite food tours in Boston .
• Grab some cannoli at Mike’s Pastry.

Hotel suggestions in Boston:

Splurge: Boston Harbor Hotel . A 5-star waterfront hotel that’s more than worth the splurge to kick start your amazing road trip through New England. The location is also convenient to a lot of attractions.

Moderate: Revere Hotel Boston Common . I stay here a lot when I visit Boston. It’s a great location that’s walkable to a lot.

Budget: HI Boston Hostel . Boston is typically an expensive city to visit unless you’re coming in the winter, and this hostel is a great option to save some money during your stay. It also has an awesome location.

Day 2: Woodstock, Vermont (2h 15m From Boston)

Why Woodstock Next? No trip to New England is complete without a stop in a charming Vermont town, and Woodstock is the best of the best when it comes to idyllic scenery and character. It’s also home to “Vermont’s most beautiful address,” which I’ll tell you about under the suggestions on where to stay.

Woodstock has a wonderful town center, where you’ll find independent shops, cafés, and restaurants, covered bridges, farms, and it’s also surrounded by beautiful rural scenery once you drive outside of town. It’s the perfect option for this itinerary if you’re hoping to get a glimpse of Vermont.

Here are some awesome things to do in Woodstock, VT:

• Meander through the most adorable village where all the shops and restaurants are. This part of town is entirely walkable, so park and enjoy!
• Visit the three covered bridges: Middle, Taftsville and Lincoln.
• Explore Billings Farm & Museum.
• Taste local maple syrups and cheeses at Sugarbush Farms.
• Take a drive to Farmhouse Pottery, just outside of the town center, which is now a famous ceramics shop – they have a studio on-site where you can watch artisans at work, or you can book a pottery session with them!

Psst! I have an entire post all about the best things to do in Woodstock, VT , if you’d like more ideas and info 😉

Where to stay in Woodstock, VT :

Luxury option : Woodstock Inn & Resort (Vermont’s most beautiful address!). It’s a splurge, but located right in town, and the perfect way to treat yourself for a 1 night stay.

Moderate: 506 On The River Inn . Very beautiful hotel that’s right on the river and feels cozy.

Budget : The Vesper . A cute little B&B with modern rooms, great prices, and walkable to the village.

Insider Tip s: Woodstock tends to be an expensive place to visit, so if you’re on a budget, the nearby town of Quechee is a great alternative, and is only about 15 minutes from Woodstock. Quechee is also very cute and I love visiting both towns when I’m in the area.

Also, if you visit in the fall during foliage, or your stay happens to be on a weekend, some of these hotels may have a 2-night minimum stay requirement, so keep that in mind.

Alternative Option: If you would prefer to spend 2 nights in Boston and skip Woodstock, you can most definitely do that. Boston is a great place for day trips to other nearby areas, including Provincetown on Cape Cod, as well as Salem. A ferry will take you from Boston to Provincetown, and to Salem, so you still won’t need to pick-up your rental car right away if you choose this option. These ferry options are seasonal, so plan accordingly.

→ Click here to check out ferries from Boston to Provincetown

→ Click here to check out ferries from Boston to Salem

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: The White Mountains, New Hampshire (1h 30m From Woodstock)

Why White Mountains Next? They’re on the way to Acadia National Park (which is the next stop!), and they’re very worth your time ( especially if you’re traveling in the fall season). The White Mountains are home to a great mix of cute towns, epic mountain views, and amazing parks or hiking and scenic drives.

While the White Mountains doesn’t necessarily offer that New England charm you’re probably expecting, I still think this region is worth visiting on your way to Acadia for the reasons mentioned above. The drives through the White Mountains National Forest, and Crawford Notch State Park is so beautiful, and offer such a well-rounded perspective of New England’s beauty, when you combine this region with all the other coastal stops on the rest of this itinerary 😉

Here are some awesome things to do in the White Mountains:

• Explore Franconia Notch State Park , and with 1 day, I suggest prioritizing Flume Gorge, which is perfect for all ages, and one of the most popular attractions in the entire state that’s worth your time.
• If you’re looking for a fun hike, the Artist Bluff Trail offers incredible views of Echo Lake.
• Ride the Cannon Mountain Aerial Tramway to the mountain’s summit for awesome views.
• Explore The Basin, which is very close to Flume Gorge, and is very quick and easy.

Where to stay in the White Mountains? I highly suggest Littleton . It’s a charming little town with awesome shops and restaurants (it’s often regarded as having one of the best Main Streets in the U.S.!), and it’s also very close to some of the top must-see things from my list above, making it super convenient and efficient for 1 day.

However, I have an entire detailed post on where to stay in the White Mountains , if you’re looking for more of a breakdown of the towns, and my hotel suggestions.

Hotel suggestions in Littleton :

Thayers Inn : Located right on Main Street in the heart of downtown, and very cozy. Keep in mind that this is a historic hotel, so they’re not able to make a lot of modern updates, so it’s not for everyone – but I really enjoyed my stay here and appreciated how it felt like I was stepping back in time!

Hampton Inn : A nice option that’s on the commercial side of town, but very close to the highway to get around quicker.

Pro Tip: You’ll drive right past Hanover, NH on your way from Woodstock, which is home to Dartmouth College, and is a really adorable little town to stop in for lunch, or to take a driving break. Right in the same area is Norwich, VT, which is home to the King Arthur Baking Company campus , and is a really fun spot to pick up some baked goods (especially breads and pastries!) and also have lunch outside on their lawn.

Here are some posts you may find helpful while you plan your time in the White Mountains:

• Things To Do In Franconia, NH
• Things To Do In Littleton, NH
• Things To Do In Lincoln, NH

Days 4-5: Acadia National Park & Bar Harbor (4h 30m From The White Mountains)

Why Acadia National Park & Bar Harbor Next? Acadia is one of the most incredible and iconic destinations in the Northeast, and definitely one of the best places to visit in New England . Even though it’s pretty far north, it’s so worth it for the stunning views. I’ve budgeted two nights here because your drive from the White Mountains to Acadia is a bit longer, and because Acadia just warrants extra time.

Also, Bar Harbor, I think, it’s such a quintessential coastal New England town filled with character. The town is small, and very walkable, and you’ll get some nice views of the bay and harbor just by walking along the town’s waterfront.

There’s also opportunities for boat tours from town, great restaurants to choose from, and of course, quick access to Acadia!

Here are some awesome things to do in Acadia National Park for a short trip:

→ Walk Ocean Path , which connects Sand Beach to the Otter Cliffs. This is the perfect scenic walk to tackle with a short amount of time because it’s easy, and offers some of the best and most iconic views of the coastline.

→ Thunder Hole is along Ocean Path, so you’ll pass right by it if you walk this trail. If you’re there on a windy day, the waves will crash so loudly that it sounds like thunder. Otherwise, it’s just a scenic overlook that’s still worth a stop.

→ If you’d like to tackle a hike, a nice one for a quick visit to the park is Great Head . This starts at Sand Beach, and is pretty easy (with some rock scrambling at the beginning), but offers incredible views along the way). After this, you can walk back across Sand Beach and do the Ocean Path for the perfect day in Acadia.

→ Lunch at the Jordan Pond Restaurant is also really fun, and a more relaxing way to spend some of your time in the park. It’s open seasonally only, so plan accordingly, and is famous for their popovers, and incredible views of the famous Bubble Rocks.

→ Sunrise at Cadillac Mountain is one of the most popular things to do, and definitely worth your time! This location is one of the first places in the U.S. to watch the sunrise, and it’s the actually first sunrise spot between October 7 through mid-March. This is another great reason to spend two nights here. Note : Reservations are now required when taking the auto road to Cadillac Mountain’s summit mid-May through October . Click here for more info!

→ Cover more ground by renting E-bikes to explore the park!

→ Click here for more info on renting E-bikes for your trip to Acadia

Psst! I have a few posts on Acadia that you may find helpful, including:

• My Perfect Acadia National Park Itinerary
• The Best Time To Visit Acadia National Park
• Visiting Bar Harbor & Acadia National Park In The Winter

Where to stay while visiting Acadia National Park? Bar Harbor! This lovely little coastal town is the gateway to Acadia, and where most people stay when exploring the park. This is another reason why I’ve given you two days because Bar Harbor is also a worthy town to explore on its town.

Hotel Suggestions in Bar Harbor :

Bar Harbor Inn & Spa : Located right on the waterfront in town, it’s a great place to stay for walkability to town, and if you’re looking for the best amenities and a nicer place to stay.

Bar Harbor Villager Motel : An awesome motel in the center of Bar Harbor’s village, with spacious and updated rooms, and walkable to everywhere in town. I like to stay here when I plan to spend most of my time hiking in the park, and just need a cozy place to crash at night.

Pro Tip : When driving from Littleton to Acadia, I suggest driving to Lincoln, NH first, and then taking Route 112 to Conway, which is the famous Kancamagus Scenic Highway. This drive takes you through the heart of the White Mountains with some really nice overlooks to stop at, and only adds 30 extra minutes to your drive (plus extra time for any stops you make).

Pro Tip : The Kancamagus Scenic Highway does not have bathrooms, gas stations or cell service, so plan accordingly!

Day 6: Portland, Maine (3h From Bar Harbor)

Why Portland Next? Not only is Portland a very cool city with lots of history and an awesome culinary scene, it’s also on the drive back toward Boston. Portland has a great mix of urban vibes and authentic fishing port scenery, so it offers the best of both worlds, too.

Here are some awesome things to do in Portland:

→ See all 3 of Portland’s lighthouses . If you only have time for one, however, make it Portland Head Lighthouse. This is one of the best lighthouses in New England, and definitely worth your time! But keep in mind that the other two lighthouses (Bug Light and Spring Point Ledge Light) are a very short drive away, so it’s easy to see all three in a few hours at most.

→ Take a tour! This culinary walking tour of the city is a great way to enjoy the best food, and this tall ships cruise around the bay is an awesome scenic option to get the most out of your visit.

→ Go beer tasting . Portland is home to some of the best breweries in New England, and the city has tons of them. I have an entire guide on my favorite breweries in Portland, Maine , if you’d like some suggestions 😉

→ Wander through Old Port , the most historic and charming part of the city.

Hotel Suggestions in Portland:

Splurge : The Press Hotel . It’s right on the water and in the center of Old Port, making this an awesome hotel to splurge on for a fancier stay in Portland.

Moderate: Cambria Hotel . Also in the Old Port district, this lovely hotel has modern rooms and a great location.

Budget: Black Elephant Hostel . Portland tends to be a pricey city to visit, and even though this is the only hostel in the city, it’s incredibly well-regarded, and will be significantly less expensive than a hotel.

Pro Tip : If you would rather spend your first day in Portland exploring the city, you can do the lighthouses the next morning on your way back to Boston. The lighthouses are located outside of the city’s downtown in South Portland, which you’ll pass through on your drive to Boston.

Optional stop to make on the drive : There are some wonderful towns to explore on the drive from Bar Harbor to Portland, and I detail my favorites to suggest in my guide on driving from Portland, Maine to Acadia National Park . Many of these stops will add extra time to your drive, but depending on your road trip style, they may be worth it for you!

Day 6: Alternative Option: Stay In A Smaller Coastal Town Instead

If staying in a city isn’t exactly your speed, and your goal is to visit more of the smaller towns along the coastal, well I’ve got you covered. And honestly, that’s usually my preference, too 😉 While I love Portland, and think there’s some very cool things to see there, one of the best parts of New England is the charming smaller towns to explore.

My favorites to suggest for this road trip are: Boothbay Harbor, Kennebunkport, and Ogunquit.

Boothbay Harbor is a wonderful, charming little town on the water, and has a more fishing village vibe to it. Lots of awesome boat tours depart from here, too.

Kennebunkport perfect encapsulated New England coastal beauty with a wonderful town center called Dock Square, and beautiful coastline near the beaches and on Cape Porpoise.

Ogunquit is also very idyllic, and is known for having one of the best beaches in New England. I love the walkable downtown that’s also walkable to the beach. Ogunquit also has one of my favorite things to do in all of New England: the Marginal Way coastal walk.

All of these places will make a great place to spend a night on this road trip if you’d prefer a small coastal town over staying in a city like Portland.

Psst! I have detailed guides that may help you decide, which are the best things to do in Boothbay Harbor , and the best things to do in Ogunquit .

Day 7: Back To Boston With Stops Along The North Shore (2h Without Stops)

Why The North Shore Next? As you make your way back to Boston, you’ll drive down the Massachusetts North Shore, which is packed with gorgeous and charming little coastal New England towns . These towns are all pretty close to another, too, which makes it easy to stop in quite a few during your drive. These towns are actually some of my favorites in all of New England.

Here are some more towns you can choose to stop in on your drive back to Boston:

→ Portsmouth, NH – while not technically part of the North Shore, it’s along the route, and a very beautiful coastal city with awesome shopping and restaurants.

→ Newburyport, MA – Some of the best shopping in New England can be found here in Market Square and Tannery Marketplace. It’s also home to Plum Island.

→ Rockport, MA – One of my all-time favorite coastal towns because it’s so unique and loaded with character. This one is a bit of a detour off the main route, but not by much (and worth it, in my opinion).

→ Salem, MA – Most known for its Halloween celebrations, but is a very beautiful and charming city that’s awesome year-round.

→ Marblehead, MA – An underrated town that’s very beautiful and historic, and loaded with gorgeous coastline.

Where you choose to stop will largely depend on how much time you have, and I honestly think they’re all worth your time! Of them all, I think I prefer Rockport the most, as I think it has the most unique scenery,, but you can’t go wrong with any of the places I mentioned above. I’ve been to them all, and continue to visit them all regularly 😉

Here are some posts that will help you plan your drive down the North Shore:

• Best Things To Do On Cape Anne (part of the North Shore)
• Best Things To Do In Marblehead, MA
• Best Things To Do In Rockport, MA
• Best Stops To Make Driving Boston To Portland, Maine
• Best Things To Do In Newburyport & Plum Island

Alternative option : If you didn’t stop in Ogunquit or Kennebunkport the night before, these two coastal towns are also worthy of your time!

10 Day New England Road Trip Itinerary

With 10 days for your New England road trip, we can pack even more exciting places to visit into your itinerary!

I’ve broken down this 10 Day New England road trip itinerary for you below, and since many of the same stops are included, I’ve done a more abbreviated version. You’ll want to refer to the above 7 Day Itinerary for all the important information. But don’t worry! I’ve included all my pro tips for the new additions to this option, too.

Days 1-2 : Boston , with an optional day trip to Salem, Provincetown or a whale watch tour from Boston’s Harbor. Since you have the extra day, I suggest taking a day trip to one of these 3 destinations, but if you would prefer to relax and explore the city even more, you can do that, too.

Day 3 : Newport, RI .

Why Newport, RI Next? It’s only 1 hour and 30 minutes from Boston, and such a beautiful coastal town to visit in New England. Because of its location, it makes it easy to squeeze into a 10-day New England itinerary, too.

Here are some suggestions of awesome things to do in Newport, RI:

• Explore Cliff Walk.
• Tour the stunning Gilded Age mansions.
• Have lunch at Cliff House.
• Take this awesome morning mimosa boat tour in Newport!
• Explore the city by trolley, which includes The Breakers mansion!

Psst! I have a detailed guide on the a Newport, RI day trip , which is helpful for 1-night stays, too 😉

Newport, RI hotel suggestions:

Splurge: The Cliffside Inn , which is walkable to Castle Hill Lighthouse, pictured above!

Moderate: Mill Street Inn , which is in a historic building that’s walkable to a lot of places downtown, including the waterfront. They also have a great rooftop patio!

Day 4 : Woodstock, VT

Days 5 : White Mountains, New Hampshire

Day 6-7 : Acadia National Park & Bar Harbor

Day 8 : Boothbay Harbor, ME

Why Boothbay Harbor Next? As mentioned, one of my favorite little coastal towns in Maine is Boothbay Harbor because it’s loaded with charm and character, and offers so many incredible opportunities to get out onto the water with boat tours. Of all the places you can stop at on your way from Acadia to Portland, this is one of my favorites.

Here are some wonderful things to do in Boothbay Harbor:

• Take this awesome boat cruise to see seals, lighthouses and a lobster haul tour!
• Stroll through the adorable downtown area.
• Take in the views from the footbridge.
• Have a delicious lobster roll at Shannon’s Unshelled.

Hotel Suggestion in Boothbay Harbor:

The Harborage Inn on the Oceanfront is my favorite place to stay in Boothbay Harbor. The location is perfect and walkable to town, but set back enough so that it’s very peaceful. If you can, splurge on Room 8 for panorama views of the water (it seriously feels like you’re floating on water).

Day 9 : Portland, ME

Day 10 : Back to Boston, making stops along the North Shore on the way.

A lternative suggestion : If you wanted to skip Woodstock, VT for this option, you could add an extra day in the White Mountains. You could also skip Woodstock and add a night in the North Shore on your drive back to Boston. For this option, I would suggest Newburyport.

Do I still think Woodstock, VT is worth the excursion? Yes! But an extra day in the White Mountains or a night in the North Shore may appeal more to some of you, too. Do what fits your preferences the most 😊

I love Newburyport because it’s a wonderful balance between charming coastal town and historic shopping village. It pretty has much something for everyone, including a beautiful waterfront park, the nearby Plum Island for beaches and nature trails, and some of the best shopping in New England. For this particular itinerary, I think it’s a great option because it’s also the furthest north, and will break up your trip nicely.

Here are some fun things to do in Newburyport:

• Induldge in some retail therapy in Market Square and Tannery Marketplace.
• Walk the path in the Waterfront Park.
• Explore Maudslay State Park .
• Drive to Plum Island to see the beaches and the nature trails at Parker River National Wildlife Refuge.

Newburyport hotel suggestion:

Compass Rose Inn is the best place to stay in Newburyport and feels like a big, warm hug when you arrive. In a beautiful and historic home, and each room is a suite with a fireplace. It’s also walkable to town, and a complimentary breakfast is included.

5 Day New England Road Trip Itinerary

Don’t have 7 or 10 days for a New England road trip? No problem! Having put a lot of thought into the best 5 Day New England itinerary, you can easily make this a jam-packed road trip style trip, or a more relaxing getaway that allows you additional time at each destination, but doesn’t get to as many places. Not sure which is right for you? I’ve outlined both to help you decide.

As before, refer to the first 7 Day New England road trip itinerary option for more detailed information on each destination.

5 Day Road Trip Itinerary From Boston

Day 1 : Boston

Day 2 : The White Mountains, New Hampshire

Day 3-4 : Acadia National Par k

Day 5 : Drive back to Boston , stopping at the Portland Lighthouses, and 1-2 towns along the North Shore region on your way.

5 Day Relaxed Itinerary From Boston

Days 1-2 : Boston. Two days will allow you to settle in and enjoy a more relaxed pace.

Pro Tip : If you’re not flying into Boston (ie, you’re driving in), you don’t have to stay right in Boston. You can definitely stay in a cute nearby town like Salem or Gloucester, and then take a day trip to Boston for a more relaxing getaway.

Days 3-4 : Newport, RI & Mystic, CT. From Newport, Mystic, CT is only about a 1-hour drive, which makes this an easy and relaxing afternoon excursion that’s stress-free.

Psst! I have a detailed guide on the best things to do in Mystic, CT , if you need more ideas 😉

Day 5 : Back to Boston, with stops in either Plymouth and Scituate on the way back (or both!). These two towns are south of Boston, and more convenient to visit when driving from Newport. I love them both, and they offer lots of charm, shopping, dining and beautiful sites to see. Of the two, Scituate is smaller with fewer things to do, but very beautiful.

Alternative suggestion 1 : Stay right in Boston for all 5 days, and take day trips! Since Boston is in such a great area, it’s very easy to get around. And as mentioned before, you can take a ferry to Provincetown on Cape Cod, or over to Salem, and you won’t need a car for either of these two excursions.

Alternative suggestion 2 : Stay in Boston for 2-3 nights, and spend 2-3 nights on Cape Cod with a day trip to one of the islands (Nantucket or Martha’s Vineyard). This option will be very coastal, and provides you with some of the best beaches and coastal towns in Massachusetts.

Here are some posts that may help you if you like this option:

• Best Towns To Stay In On Cape Cod
• Best Things To Do In Provincetown, MA
• Cape Cod Day Trip Guide
• Martha’s Vineyard Day Trip Guide
• Nantucket Day Trip Guide
• Is Nantucket Or Martha’s Vineyard Better For A Day Trip?
• How To See Martha’s Vineyard Without A Car

Alternative suggestion 3 : Stay in Boston for 2 nights, and then drive to the North Shore for 2 nights, and then maybe Portland for 1 night. Just north of Boston, the North Shore region includes Salem, Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Essex and Newburyport. All of these towns are pretty close to another another, and it would be easy to pick one to stay in, and take afternoon trips to the others.

Portland is also within 1 hour and 30 minute at the most from these towns, making it easy to pop over for the day, or a night.

Best Way To Get Around New England

The best way to see New England is definitely by car. If you fly in, I suggest renting a car from the airport to begin your road trip. If you plan to spend a day or two in Boston before beginning the road trip, I would say to hold off on renting your car until you’re ready to leave Boston.

Boston has an awesome public transit system, and Uber and Lyft are readily available, so a car will be more of a hassle to park in the city.

What To Pack For A New England Road Trip

This will, of course, depend on entirely on the time of year you visit, as New England is a four-season climate. I always suggest checking the weather reports a few days before leaving to get a more accurate idea of what the weather and temperatures will be like.

I love to remind people that New England can be moody and weather can change frequently. Even in the summer, you could have chilly days, and in the winter, you might experience a warm day. Although, generally speaking, you’ll find it’s pretty much what you would expect of a four-season climate: A wet and rainy spring, a warm or hot summer, a chilly fall, and cold and snowy winter.

Here are a few suggestions and tips on packing for a New England road trip that you not have thought of:

→ A reusable water bottle to reduce single-use plastic.

→ Dramamine if you plan to do any boat tours, and you’re prone to seasickness.

→ Day pack for essentials like your water bottle, camera, sunscreen, etc.

→ Comfortable shoes for exploring towns. Keep in mind that places like Boston, Nantucket, and historic small towns often have uneven cobblestone or brick streets.

→ Hiking boots if you plan on doing any hikes.

→ In general, plan to keep your clothes fairly casual. New England can be fancy if you plan a special dinner out, but is overall pretty casual. Take a look at your specific plans and eliminate any extra fancy outfits that you likely won’t need. You probably won’t need any if you don’t plan to dine out anywhere upscale.

→ Light jackets or sweaters for mornings and evenings (even in the summer!).

→ Waterproof jacket and boots if you plan to visit in the spring or fall.

→ Don’t forget your camera! You may also want to consider an iPhone tripod with a remote shutter to elevate your travel photos from selfies to wall-worthy shots. This one on Amazon is inexpensive and perfect for the average traveler!

New England Road Trip FAQ

Is new england easy to drive around.

Very! Of course, you’ll experience traffic when you’re close to, or in, a city like Boston or Portland. In that case, it’s just like driving in any other city. But overall, New England is very easy to drive around.

One thing I like to remind people is that in the more rural places, you will likely drive on a lot of dirt roads, so just be careful of any pot holes and go slowly, especially in Vermont and New Hampshire.

Is It Safe To Take A Winter New England Road Trip?

Yes! As long as you’re comfortable driving in the snow, you’ll be totally fine. Chances are, if you’re visiting in the winter, you’re excited to check out places like New Hampshire or Vermont, and those two states are among the top 3 snowiest in the whole country. So, just know that you will experience snow, and you’ll definitely be driving in it.

But generally speaking, most places are great at plowing roads, so unless you happen to visit during one of our big nor’easter storms, driving is easy. Just practice normal precautions, and don’t drive if the snow is coming down really hard.

I have an entire guide on all my favorite New England winter getaways , if you’re looking for the best winter destinations in this region.

Is Cell Service Reliable All Over New England?

Yes and no, and it depends on where you’re going. For the most part, cell service is completely reliable, and Google Maps will be able to take you everywhere.

However, in more remote places, again like in Vermont or New Hampshire, or even along the coast at some lighthouses or in Acadia, you will lose cell service more than you think! I highly recommend offlining maps for your entire route just to be safe . I can’t tell you how many times I’ve lost service while driving in VT and NH and didn’t offline maps, only to very much regret it in the moment!

Why Is Connecticut Not Part Of Your Itineraries?

I love Connecticut! But the hard thing about it is its location. It’s so far southwest, in the exact opposite direction of Acadia National Park, and most of the other top destinations to visit. And since Acadia is one of the most amazing New England locations that everyone should see when they visit, I had to exclude Connecticut from the itinerary options only for the sake of time. I personally think Acadia, and the other places I’ve mentioned, offer much higher payoff for your driving time than destinations around Connecticut.

That’s why I was only able to squeeze in a quick afternoon trip to Mystic, CT in the 5-day option.

What About A Fall Foliage Road Trip?

I’ve got you covered! I have an entire post on the perfect New England fall road trip , which is one I’ve perfected over many years of exploring this region in the fall season. This road trip makes stops in similar places, but has more of a focus on the best places for foliage.

You May Also Enjoy Reading:

• Best Things To Do In New England
• Best Time To Visit New England
• Incredible New England Resorts & Spas
• Best Boston Hotels Near The Aquarium
• Awesome New England Gifts & Things To Buy During Your Visit
• Best Christmas Towns in New England
• Best New England Day Trips
• Summer In New England: Best Places To Go & Things To Do!
• Best Beach Towns In New England
• Things To Do In Boston In The Fall
• Gorgeous New England Islands Worth Visiting
• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary

That’s A Wrap On The Best 7 Day New England Road Trip Itinerary

Hopefully you’re now feeling ready to tackle planning your own adventure with this 7 Day New England Road Trip Itinerary! Even with 7 days, you can see so much of this gorgeous region and really cover a lot of ground. And, of course, if you have time to follow along on my 10 Day New England Road Trip Itinerary, that’s even better. But regardless of what you have time for, New England is always a good idea, and is always worth making time for. Happy planning!

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New England Explorer

13 day fly drive – from £1635, with flights from £2185.

This 13-day fly drive holiday begins in the bustling city of Boston and weaves its way through the historic charm of New England’s towns, coastlines and mountains.

Highlights:

• Walk the Freedom Trail to experience Boston’s rich history
• Experience the artistic and natural beauty of The Berkshires
• Discover the enchanting seaside town of Bar Harbor
• Witness the lush beauty of the Green Mountains
• Bask in the tranquil beaches and quaint charm of Cape Cod

Your Itinerary

You can customise this itinerary by adding extra nights or destinations. Just let us know what you would like to do

Day 1 – Welcome to Boston

Arrive in Boston make your way to your first hotel. The rest of the day is yours to do as you please , a recommendation is to visit the Boston harbour where you can enjoy The Boston Harbour Walk. This walk is designed to connect the public to a clean and restored Boston Harbour. Alternatively, you could visit Faneuil Hall Marketplace comprised of a collection of boutiques, eateries and pushcart vendors housed in converted 18th-century warehouses.

Boston Park Plaza or similar

Day 2 – Boston

Spend a full day exploring this historic town. Take a walk along the famous Freedom Trail, one of Am ericas’ first historic walking tours and the perfect introduction to Colonial and Revolutionary Boston. You will visit 16 historical sites covering two and a half centuries of America’s most significant past.

Optional Experience – Boston Old Town Trolley Tour Hop aboard one of these trolleys and you’ll experience ‘Transportainment’, a delightful combination of transportation and entertainment. Turn back the pages of history and relive colonial Boston. Coming from various backgrounds, each conductor narrates the sightseeing tour with his or her own blend of trivia, colourful anecdotes, and humorous stories to ensure that your experience is both enjoyable and informative.

Day 3 – Kennebunkport

Collect your car this morning and leave Boston behind as you drive north toward Salem, the infamous  home to the witch trials of 1692. Well aware of its infamy, Salem has a number of attractions centred on this uneasy time, including haunted tours and re-enactments. Continue the drive passing Gloucester, America’s oldest fishing port, toward Kennebunkport, a great place for hiking and exploring.

Nonantum Resort or similar

Day 4 – Bar Harbor

This morning get to know Kennebunkport and all its natural wonders like Spouting Rock and Blowing Ca ve. In the afternoon continue the journey to Bar Harbor. Located in Downeast, Bar Harbor was once considered a small fishing and ship-building community; today it’s a favourite destination for people throughout the world, offering spectacular beauty and natural wonder for those who would prefer to spend their time outdoors.

Bluenose Inn or similar

Day 5 – Bar Harbor

Today you can explore Bar Harbor and its surroundings at your leisure. Visit Mount Desert Oceanariu m which includes a lobster museum, a marsh tour, and a lobster hatchery. For a touch of nature, visit Acadia National Park, New England’s only National Park; it offers 6000 acres of mountains, rugged coastline, islands, forests and lakes where you can hike, bike, canoe, fish, and explore this Park’s trails.

Optional Experience – Lobster Boat Cruise Experience a sample of the life and work of the Maine Lobsterman. Watch as the captain demonstrates how lobster traps are hauled while learning all the parts of a lobster trap and how the lobsters find their way to the bait inside. Learn all about the anatomy and life cycle of the Maine Lobster. In addition to lobster and crab, you’ll see and be able to touch sea urchins, starfish, and sea cucumbers. The kids will love it and so will you. About halfway through our cruise, we’ll stow all the lobster gear and then head off to a small island to look at harbour seals basking on the rocks or swimming in the nearby water.

Day 6 – White Mountains

Continue on your journey through coastal Maine to Jackson. Take a scenic drive to the White Mountain s National Forest, better known as the Whites. Take a train ride through this scenic area; choose one of the Valley routes to Conway or Bartlett, or the legendary Crawford Notch excursion.

Christmas Farm Inn or similar

Day 7 – Stowe

As you leave this morning, through the White Mountains, visit Franconia Notch State Park located in  the heart of the White Mountain Region. Here you can ride a passenger cable car to the top of Cannon Mountain where on a clear day you can see mountains in Canada, and you can visit Mount Washington, the highest Mountain peak in the Northeast. After a scenic stop and some great photo ops, continue on to the Stowe area in Vermont.

Green Mountain Inn or similar

Day 8 – Green Mountains

After a night in Stowe it’s time to head towards the Green Mountains. On your way, you will pass ‘Mo ss Glen Falls’, a roadside attraction featured in just about every photographic portrait of Vermont ever published. You can also visit the Smugglers’ Notch State Park in the Green Mountains; it’s great for hiking and offers several short, medium and long trails throughout the park.

Snowed Inn or similar

Day 9 – The Berkshires

The Berkshires are a beautiful place to visit any time of year, the area is known widely as a cultur al hub of museums, historic sites, music, dance and art venues. In addition, the region also offers outstanding opportunities for outdoor sports including golf, hiking and mountain biking, fishing, and even white-water rafting. All of these activities take place amid spectacularly scenic rural hills dotted with mountain streams and lakes.

Red Lion Inn Stockbridge or similar

Day 10 – Newport

Leave the Berkshires behind and drive on to Newport. Home to spectacular coastal scenery, awe-inspir ing architecture, a thriving waterfront, and welcoming hospitality, Newport is considered by many to be a shining gem in the coastal crown of New England. Take a walk through tennis history and explore six acres of historic grounds at the Tennis Hall of Fame, enjoy the peaceful waters of Narragansett Bay aboard the Newport Dinner Train, or visit Bannister’s Wharf, an old commercial seaport in the colonial days, now the hub of Newport’s harbour side shopping and dining. Here you can find eclectic boutiques and numerous restaurants from the sophisticated to the casual.

OPTIONAL EXPERIENCE – Newport Mansion Tour Visit two of the famed Gilded Age mansions that once were the summer playground for socialite families. With names like Breakers, Astor and Vanderbilt, they are by far the most popular attraction in Newport. Built near the turn of the century, these magnificent structures are each a museum onto themselves. Here you will find a world of exceptional elegance and inspiration in architecture, art, interior design and landscapes.

Newport Beach Hotel & Suites or similar

Day 11 – Cape Cod & Falmouth

People come to Cape Cod to feel inspired; to walk the pristine beaches, revel in the arts and cultur e, indulge in the freshest fried clams, play 18 holes on the lush fairways, and savour the breathtaking scenic beauty. Lighthouses, cultural landscapes, and wild cranberry bogs offer a glimpse of Cape Cod’s past and continuing ways of life.

Inn on the Square or similar

Day 12 – Cape Cod

Today you can make a decision between visiting Martha’s Vineyard or Nantucket Island, both are next  to Cape Cod and both are full of charm and typical New England atmosphere. The best way to see the prettiest spots on the islands are on foot, bicycle or a combination of the two. There’s so much to see and do on both Island’s the decision of which way to go may not be an easy one. 

Day 13 – Farewell from Boston

On your last day, on your way back to Boston, you may wish to visit historical Plymouth Rock a monument symbolizing the location where the Pilgrims disembarked from the Mayflower when they first landed on what was to become American soil. You can also see the Mayflower II, a replica of the ship that first brought settlers to New England. 

Welcome to Boston

Kennebunkport, white mountains, green mountains, the berkshires, cape cod & falmouth, farewell from boston, this self drive includes, flights & more.

With FREEDOM, you can book your New England Explorer fly drive and flights together, as an ATOL protected package. Our Travel Experts can find the best priced Economy, Premium or Business Class flights for you.

You can also personalise your holiday. Why not add:

• Extra nights in Boston, the Green Mountains or any location en route
• A Boston Old Town Trolley Tour, Lobster Boat Cruise or Newport Mansion Passport

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

Price is per person, based on two people sharing a double or twin room and includes pre-booked accommodation, air-conditioned car and unlimited mileage. One-way fees charged locally. Hotels specified are subject to availability and may be substituted by one of a similar or higher standard.

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Self Drive Tours

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There is so much to see & do in New England so the best way to explore what it has to offer is to get into the car and hit the open road. With 6 states and hundreds of miles of road to cover, it can be a hard task to try and map out where you want to go, how long you want to stay and how you are going to get there without missing some must-see attractions. So using our expert knowledge of New England, Purely New England have put together a wide range of self drive tours designed to show you the best of New England. All of our tours include accommodation, driving directions and an extensive tour itinerary pack to ensure you will not miss any of the highlights  New England has to offer.

Our self drive tours below have been carefully selected and our range enables you to choose the holiday experience that will suit you best, every tour is flexible so feel free to let us know if you want to make any changes or w e can also tailor-make a self drive tour just for you , contact us on 0844 80 444 80 or email us your requirements then leave the rest to us!.

Click on any of the boxes below to view the Self Drive Tours itinerary and costs.

A Taste Of New England

Graceful New England

Luxury 4 Center tour

Jewels Of The Atlantic

Best Of Boston, Cape Cod & Martha's Vineyard

New England Panorama

New England Discovery

Self Catering Tour

New England Country Inns

New England Showcase

"Lark" Around

New England 

NEW (Boutique hotels)

Classic New England

Our Best Seller !

New England & Niagara Falls

Noble New Hamsphire

Magnificent Maine

Very Vermont

Southern New England

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Exploring New England’s Fall Foliage: Self-Guided Tours

Autumn in New England is synonymous with vibrant foliage, crisp air, and picturesque landscapes. If you’re seeking the best places to immerse yourself in the season’s splendor, look no further. We have curated a list of 14 self-guided New England fall foliage tours, each offering a unique perspective on this enchanting season.

1. Acadia National Park (Driving)

Acadia National Park, located in Maine, presents a vast canvas of crimson, gold, and amber. Embarking on this self-guided New England fall foliage tour, drive through scenic loops offering panoramic ocean and mountain views. Don’t miss the summit of Cadillac Mountain; on clear days, it’s the first place in the U.S. where you can see the sunrise.

2. Bar Harbor (Walking)

A coastal town adjacent to Acadia, Bar Harbor is a haven for walking enthusiasts. Stroll through its charming streets, filled with local shops and restaurants, all while surrounded by the brilliance of autumn leaves.

3. Blue Ridge Parkway (Driving)

The Blue Ridge Parkway, often referred to as “America’s Favorite Drive”, is a testament to nature’s majesty. A medley of autumnal hues and breathtaking mountain backdrops will accompany you as you drive.

4. Boston Freedom Trail (Walking)

Historic and scenic, the Freedom Trail in Boston is a 2.5-mile-long path through 16 historically significant sites. As you delve into America’s history, the autumnal canopy overhead adds a special touch to the journey.

5. Boston Harbor (Walking)

Experience architecture on Boston Harbor’s waterfront while the cityscape dons its fall attire. This walk offers a blend of history, modernity, and nature’s seasonal artistry.

6. Cades Cove (Driving)

Tucked within the Great Smoky Mountains, Cades Cove is a broad valley surrounded by mountains. The looped drive offers unparalleled views of wildlife, historic buildings, and the golden hues of fall.

7. Cambridge (Driving)

Adjacent to Boston, Cambridge is famous for its esteemed universities. Drive through its tree-lined streets, where gothic architecture gets accentuated with the changing leaves.

8. Cape Ann (Driving)

This rocky cape in north-eastern Massachusetts boasts quaint fishing villages and lighthouses. The coastal roads draped in autumnal colors make it a must-visit during the fall.

9. Cape Cod (Driving)

The charm of Cape Cod is elevated during the fall. Drive along the coastline, watching the cranberry bogs turn deep red, perfectly complementing the ocean’s blue.

10. Central Park (Walking)

New York City’s Central Park is a serene escape amidst the urban hustle. During autumn, it transforms into a vibrant spectacle, making it a perfect place for a self-guided New England fall foliage tour.

11. Great Smoky National Park (Driving)

Known for its mist-covered mountains, this national park becomes even more magical with the onset of fall. Winding roads take you through dense forests painted in shades of autumn.

12. Harvard Yard (Walking)

Situated within Harvard University in Cambridge, this historic yard is a treat during the fall. Walk amidst centennial trees showcasing a riot of colors and soak in the academic ambiance.

13. Kancamagus Scenic Byway (Driving)

This highway in New Hampshire is renowned for its fall foliage vistas. It’s an unadulterated nature drive, with the White Mountains on one side and the Swift River on the other.

14. Lexington and Concord (Driving)

Revisit the beginnings of the American Revolution as you drive through these towns. The historical significance, paired with the autumn scenery, makes it a noteworthy part of any self-guided New England fall foliage tour.

In conclusion, New England is a treasure trove of autumnal delights. Whether you prefer walking through historic cities or driving through nature’s vastness, these self-guided New England fall foliage tours promise an unforgettable experience. So, pack your bags and let the beauty of fall guide your way.

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The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)

Here’s my guide to the best one week fall foliage itinerary in New England. New England is a classic American destination, the perfect place for a road trip.

As a born/bred/educated New England girl myself, I think New England is arguably one of the world’s most beautiful places in the fall.

Country roads wind through dense forests, stone walls, covered bridges, and idyllic farm properties.

Orange, red, and gold colors explode, rippling across the mountains. It’s the stuff of dreams.

If you want to escape the crowds and fall back into nature, I recommend adding a New England road trip to your USA bucket list .

Here’s my sample one week fall foliage itinerary, taking in the best fall colors in New England. I also give you plenty of options for extending your New England road trip if you have more vacation time.

In this 7 day New England itinerary, I spill the beans on the must see scenic spots in New England to experience the festival of colors, where to stay and eat, the top hikes, and photography inspiration.

You’ll start in the historic New England city of Boston and then head to the Berkshires, Vermont, and New Hampshire. I think New Hampshire and Vermont are the best place to see fall foliage, though I may be a tad biased.

If you have more than one week for your New England fall road trip, I give you some other options in Connecticut and Rhode Island to extend your time in this rural playground.

You can easily turn a 7 day fall foliage road trip into a 10-14 day itinerary for New England and stay longer in each place.

Overview Of One Week Fall Foliage Itinerary In New England

• Day 1 : Boston MA
• Day 2 : Berkshires MA
• Day 3 : Dixville Notch State Park NH
• Day 4 : Stowe Vermont
• Day 5 : Smugglers Notch NH
• Day 6 : White Moutains NH
• Day 7 : White Mountains NH
• Extra Time? Add Burlington Vermont, Connecticut, and Rhode Island

One Week Fall Foliage Itinerary For New England

Let’s begin the leaf peeping! Here’s where to go for fall foliage with one week in New England.

Day 1: Boston, Massachusetts

Begin your 7 day fall foliage road trip by flying (or driving) into Boston . Beautiful Boston Massachusetts is one of my favorite city in the United States. And fall is the perfect time to visit.

The country’s oldest city, Boston is steeped in American history. Boston played a pivotal role in the Revolutionary War.

Boston’s sometimes called the “hub of the world” or the “cradle of liberty.” The city was the source and inspiration for key ideas that shaped America.

READ : 3 Day Itinerary for Boston

Boston has a great foodie scene, wide open green spaces, quaint neighborhoods, and first rate museums. The prettiest neighborhoods, lit in colors in the fall, is Beacon Hill .

And Boston’s got loads of gorgeous fall foliage. To see the colors, head to Boston Public Garden, Boston Common, the Boston Esplanade along the Charles River, Beacon Hill, and Back Bay.

You can book a historic walking tour . The hop on hop off trolley bus takes you to Boston’s top attractions. You can also see check out the colors on a fall foliage lunch cruise .

After touring the city, pick up your rental car. Now, it’s time for some classic new England fall foliage. If you want to skip the big city altogether on this fall foliage trip, just add in one of my bonus destinations instead.

Where To Stay In Boston:

If you opt for downtown, I like the small  XV Beacon  or the  Klimpton Nine Zero Hotel. You could also splurge at the  Ritz Carlton  or the  Four Seasons .

The  Inn at St. Botolph , the  Lenox Hotel , and the  Hilton  in Back Bay are also nice options and central too.

If you can’t resist historic Beacon Hill, check out  The Boxer ,  Liberty , or the elegant  Whitney Hotel .

Where To Eat In Boston:

Barcelona Wine Bar, SVR, Yvonne’s, Beehive, Giacomo’s, Sarma, and o ya

Day 2: The Berkshires, Massachusetts

The Berkshires are a beautiful rural region of western Massachusetts that’s made up of 30 bucolic villages with some top tier leaf peeping, museums, and restaurants.

It’s a place of fall foliage glory In New England. The Berkshires are full of winding roads with rolling meadows and trees ablaze.

For some of the best fall foliage scenery in the Berkshires, take Route 7 and 8 from Great Barrington to North Adams (1:10 hours without stops).

You’ll go past storybook farms, wooden barns, and stone walls. And through the cute towns of Stockbridge, Lee, Lennox, and Pittsfield.

Stockbridge and Lenox are the two prettiest towns in the Berkshires, and make a great base for exploring. Stockbridge is home to the Norman Rockwell Museum and some of the Berkshires’ beautiful Gilded Age castle-cottages.

Lenox is home to The Mount , Edith Wharton’s home, more iconic properties, and fantastic restaurants.

The quaint town of North Adams is an arty town with an eye catching row of multi-colored Victorians called The Porches. If you’re in the mood for a museum after some leaf peeping, there are couple really good ones.

Try the Susan B. Anthony Birthplace Museum (in nearby Adams) or the spectacular Massachusetts Museum of Contemporary Art .

The Notch Road leads to Mt. Greylock State Reservation . You can drive up to the summit for Massachusetts’ highest viewing point.

There are plenty of marked hiking trails that start from the parking lot. Click here for the online trail map.

Then descend back down, exit the park, and take Route 7. This will take you to the small town of Lanesborough, where you’ll see pastures and horse farms. You can pick your own apples at Lakeview Orchard .

Near Route 7, you can also visit the home of Edith Wharton in Stockbridge. On your way back to North Adams, you can stop in Cheshire at the Whitney’s Farm Market.

Here’s my complete guide to the Berkshires .

Where To Stay In The Berkshires :

In Lenox, you can check out the intimate Wheatleigh resort fashioned as a Florentine palazzo. The Seven Hills Inn is a historic property on beautifully landscapes grounds with cottages.

In Stockbridge, you can stay at the historic Red Lion Inn or the Inn at Stockbridge , a charming B&B.

Where To Eat in the Berkshires:

Gramercy Bistro, Nuedel, Grazie, Mezze, Bistro Zinc, or The Portico at the Wheatleigh

Day 3: Dixville Notch State Park, New Hampshire

On day 3 of your 7 day fall foliage itinerary, get up early and drive 4.5 hours north to Dixville Notch State Park to venture into New Hampshire. Dixville Notch is a very small area. But what it lacks in size, it more than makes up for in unadulterated beauty.

The main road through Dixville features rolling hills and stunning scenery, including beautiful Lake Gloriette. Once there, hike the famed Table Rock Trail. You’ll need to pull off the shoulder and park on Route 26.

Table Rock Trail is a 1.5 mile out and back trail, with a relatively steep 700 feet climb. You’ll be rewarded with panoramic views over gorgeous Dixville Notch from above. If you’ve timed it right, you can even enjoy the sunset from your perch.

Another trail leaves from the parking lot of the Whittemore Family Cemetery on Google Maps. The trail winds its way through a vibrant forest, leading to a cute little bridge and stream. When you’re done hiking, head back to the nearby town of Colebrook for dinner and shut eye.

Where to stay : La Maison Bleue du Lac, Mohawk Cottages

Where to eat : Black Bear Tavern, Parsons Street, Wilderness

Day 4: Stowe, Vermont

Wake up early, grab some breakfast at Mostly Muffins in Colebrook. Then drive 2 hours west towards Stowe Vermont.

Along the way, you’ll pass scads of beautiful fall foliage and adorable rural towns, like the memorable Island Pond in Brighton.

Spend the day exploring the charming town. Where mountainous Stowe really shines is its hiking trails, with a range of options to suit every level of experience. Some take you to towering peaks, others end in waterfalls.

For beautiful fall views of Vermont’s Green Mountains, you can ride the ferry across Lake Champlain.

Another option is taking the Gondola Sky Ride at the Stowe Mountain Resort, for more beautiful aerial mountain views.

When you’re done hiking, snack on some apple cider donuts. Stowe also has a romantic and picture perfect downtown.

Its white steepled church is the focal point. Tiny Main Street is filled with boutiques, crafts stores, and antique shops. There are libraries, museums, theaters, and cultural organizations to keep your entertained.

Where To Stay In Stowe:

Stowe has some very nice hotels. The best option is the Topnotch Resort , with pools, a spa, and saunas. The Lodge at Spruce Peak is another good option. It’s at the base of Stowe Mountain and has awe inspiring views of the area’s lakes and peaks.

You can also check out the Trapp Family Lodge , with old world Austrian charm.

Where To Eat In Stowe :

Plate, Cliff House, Bistro at Ten Acres, Green Goddess Cafe

>> Click here to book a brewery tour in Stowe

Day 5: Smuggler’s Notch, Vermont

Day 5 of your one week New England fall foliage itinerary will be a busy one.

Wake up early and head 20+ minutes to the famed Smuggler’s Notch, detouring off Route 100 to Route 108. This magnificent area has a road that goes through a gap between two mountains (termed a “notch”).

Smuggler’s Notch is similar to Dixville Notch. But it’s even more stunning. The mountains on either side are massive.

There are many beautiful twists, hairpin turns, and massive boulders in the road. Unfortunately, there aren’t many places to stop and take photos. But there are two parking lots, at the Welcome Center and upper end of the notch.

From Smuggler’s Notch, drive south to Pomfret, Vermont. Take Cloudland Road south from Pomfret to Woodstock. You’ll drive along cute dirt roads lined with fall colors, rolling hills, and quaint farms.

If you’re hungry, stop in Woodstock for lunch at Mangalitsa or the Prince and the Pauper Restaurant.

Stop for a photography break at Sleepy Hollow Farm in Woodstock Vermont. It’s a great little stop that captures one of New England’s most photogenic farm properties now Instagram famous.

Sugarbush Farm is another local farm property that you can visit. Their maple syrup is famous.

Now, it’s time to head back to New Hampshire. At the base of the White Mountains, the town of Lincoln makes a good base for touring this area.

Then you don’t have to move every night. Lincoln is a creative foodie town, so plan on some fine dining there after your days of hiking and leaf peeping.

Where To Stay Near Lincoln: Omni Mt. Washington , Sugar Hill Inn , Riverwalk Resort at Loon Mountain , Red Sleigh Inn B&B

Where to eat : The Common Man, Gypsy Cafe, La Vista Italian Cuisine

Day 6: White Mountains, New Hamsphire

On day 6 of your one weeks fall foliage tour of New England, you’ll drive the sinuous Kancamagus Highway in the White Mountains.

It’s one of the most beautiful fall foliage drives in New Hampshire . You can drive the road with this self guided audio tour .

Be prepared to pump the brakes frequently. You’ll be dazzled by the incredibly epic roadside views on this 34 mile stretch of highway.

There a few places to pull over, providing great photo opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here, you can take a walk along the Swift River and get views of the beautiful Falls Pond.

From Rocky Gorge, backtrack a short distance to drive up Bear Notch Road. Bear Notch features a scenic drive along a mountainside and more roadside pullouts for gorgeous photo opportunities.

At the end of Bear Notch Road, drive north to Crawford Notch State Park .

Here, you can explore the backroads and revel in the beautiful fall colors. If you’d like to do some hiking, there are 35 hiking trails of varying difficulty.

The best hike in this area is the Mount Willard Trail . It’s a relatively steep, but short, 3.2 mile out and back hike to a clifftop vista overlooking Crawford Notch. The views are surreal.

Next, continue driving north where you can detour to the Mt Washington Cog Railway . Here, you can ride a historic train to the summit of Mt. Washington.

The mountain is the tallest one in the northeastern United States at 6,289 feet. At night, head back to your base in Lincoln.

Day 7: White Mountains | Franconia Notch State Park, New Hampshire

On day 7 of your New England fall foliage itinerary, you’ll head to Franconia Notch State Park. The park is a lovely spot nestled in the White Mountains, just 7 minutes from Lincoln.

Start your day with a sunrise hike up to Artist’s Bluff . This is a short 1.4 mile long loop trail up to a hilltop overlooking Echo Lake. The fall foliage here is simply breathtaking.

Continue on to Flume Gorge . This is one of the best stops on a New England road trip. The natural chasm stretches 800 feet along the base of Mt. Liberty.

A boardwalk provides a relatively easy 2 mile loop hike. Waterfalls, streams, and covered bridges keep the eyes riveted the entire way.

You can also be whisked away on the 80 person Canon Mountain Aerial Tramway , which takes you to the top of majestic Cannon Mountain for an “oh wow” view. Cannon Cliff is the northeast’s largest vertical rock face. Trails meander on the mountain.

You can also hike the Falling Waters Trail to beautiful waterfalls. Or bike or hike the 8.7 mile Franconia Notch Recreation Path.

The paved trail offer spectacular views of the White Mountains and access to Echo Lake. More adventurous travelers should pull in at Loon Mountain and zipline 700 feet across the Pemigewasset River.

Where to eat : Polly’s Pancake Parlor, Lovette’s Inn & Restaurant

Extra Time On Your One Week New England Road Trip?

It may be time to head back to Boston or home after your one week New England fall foliage road trip.

But if you have extra time on your hands, there are several places you can easily add to create a longer New England fall foliage itinerary.

1. Burlington Vermont

While you’re in Vermont, after Stowe, add a day in the lovely town of Burlington. As the largest town in a state of small hamlets, Burlington has developed a wonderful art scene.

To some, Burlington is akin to a mini Seattle — a politically and socially progressive enclave of college students, regional power brokers, and creative minds.

The city’s popular waterfront bike path includes miles of paths, many along Lake Champlain. Stop at Ethan Allen Park, with a 40 foot tower providing mountain views.

If you’re a foodie, Burlington will suit. It outshines much of the US with a bounty of locally grown food. Farm to table eating is a well established tradition. There’s even excellent street food at Farmers and Foragers Food Truck.

Where to stay : Willard Street Inn, Made INN Vermont

Where to eat : Bleu Northeast Seafood, Hen of the Wood, Juniper

2. Connecticut

If you want to venture south of Boston, Rhode Island and Connecticut also offer excellent fall foliage drives, with rolling foothills ablaze in color.

The best fall drive in Connecticut is the tree-lined State Route 169. This two lane scenic road connects picture perfect towns in a still rural corner of the state, often called New England’s “Last Green Valley.”

Along this relaxing and uncrowded drive, you’ll pass classic churches, orchards, stone walls, and 19th century homes. The pink neo-Gothic  Roseland Cottage operates as a museum.

It’s open for tours June through mid-October. For a break, stop at Mrs. Bridge’s Pantry for some tea and scones.

Another popular fall drive in Connecticut is from Milford to Litchfield. Along the way, you can stop at Hunt Hill Farm, with a gallery, shop, and cafe.

Continue to New Preston, where can you do some antique shopping at Dawn Hill Antiques . Then take the 8 mile drive around Lake Waramaug. In fall, it’s encircled with red maples, rusty oaks, and yellow birches.

Where to stay : Winvian, Grace Mayflower Inn & Spa, Inn at Stonington

Where to eat : Arethusa Farm, Schoolhouse at Cannondale

3. Rhode Island

The state of Rhode Island is the home of the red maple, which turns a glorious gold, purple, and scarlet come fall.

Start your tour of tiny Rhode Island in the amazing town of Providence. Providence combines big city sophistication with small town charm, vibrant culture with hot restaurants. Here’s may one day itinerary for Providence .

For leaf peeping in Providence, the tree lined vista from Prospect Terrace is stunning. There are beautiful trees along the downtown River Walk and on historic Benefit Street.

Drive north from Providence to the Diamond Hill Vineyards, which specializes in pinot noir. Then drive west to the village of Chepachet, where you’ll find Victorian homes and antique shops. A classic stop is at Brown & Hopkins Country Store .

Then hit the road and drive another 40 miles to Exeter. It’s lined with pristine hardwood forests with an abundance of red maple, white oak, elm, and poplar trees.

If time allows, you can continue on to the Colonial seaport town of Wickford, opening to Narragansett Bay.

Where to stay : Renaissance Providence , Graduate Providence

Where to eat : Gracie’s, Al Forno, Bacaro, Birch, Chez Pascal

When Is The Best Time To Take Fall Foliage Road Trip In New England?

The best time to see New England fall foliage is typically from mid September to late October. Even until early November in some places.

But it varies somewhat by state, fall coming earlier the further north you go. Some states have foliage trackers you can check to determine when peak fall foliage occurs: New Hampshire , Vermont , Massachusetts , and Connecticut .

I hope you’ve enjoyed my one week fall foliage itinerary in New England. You may enjoy these other United States travel guides and resources:

• 25 Prettiest Towns in New England
• Must See Places in the Berkshires MA
• 1 Week Road Trip for Vermont
• 10 Day Road Trip in Coastal Maine
• Flexible 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary
• 21 Less Touristy Towns on the East Coast
• Best Art Towns on the East Coast
• Best Art Towns in California
• Famous Landmarks in Boston

If you’d like to take a fall foliage road trip in New England, pin it for later.

15 thoughts on “The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)”

I like the sound and feel of your one week foliage road trip. When would you recommend doing that trip in the fall?

Thanks Eddie! Generally, mid September to late October is the best time.

Hi Leslie, do you do custom trip itineraries? We would like to fly into Maine and make a triangle Fall tour of Maine, NH and Vermont.

Thanks for your reply!

Hi Steve, I just don’t have time at the moment. I’m about to leave the country for travel again. But there is nothing better than fall in New England!

Thank you so much for this wonderful itinerary. It’s my first trip to the New England states. I am mapping things out now. Question: if I am driving to my final destination of Toronto, Canada, should I drive in the reverse order and go from Boston to the White Mountains to Stowe to Dixvill Notch, etc….?

Yes, that makes sense to me. Enjoy your trip!

Hi. Thanks for your lovely articles and suggestions. We are going on a NE Cruise in September and have available 5 extra days after the cruise in the NE area, we will be driving from Boston. We do not want to move around every night, and after reading your article I am thinking of just going to the Berkshires (maybe Lenox) and Stowe, then touring around those areas in the time we have. My question is where would you spend more time, Berkshires or Stowe? We will do 2 nights at one, and 3 nights at the other.

Definitely the Berkshires. I have a whole article on what to do in the Berkshires, if you use the search bar. I think Stowe is a one day visit unless you’re skiing.

This is awesome information. Thanks for putting this all together. Where would you suggest to stay on Day 6 & 7 ? There are no suggested places to stay in the article. Thanks so much !

There are lots of places to stay in the White Mountains. I should probably update the article. The nicest place is the Omni Mount Washington. You can also check out the Mountain View Grand resort and the White Mountain Hotel and Resort. Or opt for booking an Air Bnb.

This was exactly what I needed! Flying into La Guardia from Texas next week. We are renting a a car and doing a 6-day tour of New England. We were planning to end in Boston so we can go from there back to the airport. Can you give me an idea of where to start with having only 5 nights? Thanks so much for sharing this great information with us newbies!

You could just reverse the order and start in the White Mountains, staying only 1 night there instead. Or you could skip the white mountains and start in Smuggler’s Notch, spending an extra day in the Berkshires. I have a Boston itinerary, if you want one: https://www.thegeographicalcure.com/post/the-perfect-3-day-itinerary-for-boston-massachusetts

Hi Leslie! We’re planning to take your New England car tour and will be driving from southwest OH. We may stay at the American side of Niagara Falls on our way to Boston. Can you offer any tips on lodging or restaurants at Niagara Falls? Thanks much!!

Sorry, no, I haven’t been there in decades. Enjoy your trip Don!

We will be able to complete 5 full of the days of your itinerary, starting and ending in Boston. (Landing in Boston Sunday night, touring Monday – Friday, flying out of Boston Saturday late afternoon).

Which 5 days would you most highly recommend we hit? We do like hiking, if that helps.

Thanks for your great post!

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Last Updated on July 4, 2023 by Leslie Livingston

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New England Fly Drive & Self Drive

New England is one of our favourite regions for hiring a car and driving along the wide open road. Journey along roads canopied by luscious foliage, explore quaint seaside owns, and wander through fun cities with historical flair. Our itineraries below offer great suggestions and ideas, and you can give our team a call to create a self-drive bespoke to you.

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A great little tour of the highlights of New England, starting in Boston. You'll experience the beautiful coastal regions of Cape Code and Maine, climb into the mountains of Vermont and New Hampshire and enjoy a stay in the Connecticut River Valley.

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This tour takes you from sophisticated Manhattan and thundering Niagara to Pennsylvania Dutch countryside and the inspiring national monuments in Washington D.C.

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Discover the great outdoors in one of the most picturesque regions of America on this motorhome tour of New England. This suggested itinerary is for two weeks, but you can choose to stay for more or less time wherever you want.

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On this picture perfect self-drive tour of New England you will discover the majestic mountains of Vermont & New Hampshire, explore the beautiful coast of Maine & Cape Cod and admire the glamorous mansions of Newport. Savour delicious seafood & farm-to-table cuisine, capturing the flavour New England.

Experience New England Self-Drive

A tailormade 10-day self-drive tour of New England. Taking in the attractions of Boston, the beautiful coastline of Maine and the White Mountains of New Hampshire. You will also explore the stunning state of Vermont and experience the lovely Cape Cod peninsula.

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Marvel at Niagara Falls, soak up stunning scenery in Cape Cod & New England, stroll delightful cities such as Boston & Ottawa, discover the history of Quebec City & Gettysburg, explore cosmpolitan Montreal & Toronto. This great circular flydrive itinerary begins and ends in New York.

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Discover the revolutionary history of Boston on a guided tour of the Freedom Trail.

Explore the rugged coastline of Maine, dotted with lighthouses and quaint seaside towns.

Wander through the picturesque villages and rolling hills of Vermont.

Take in panoramic views from atop Mount Washington in New Hampshire's magnificent White Mountains.

Go whale watching off the waters of Cape Cod.

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On arrival in Boston, make your way to your accommodation. The rest of the day is free to explore this historic city at your own speed. You could visit Harvard University, look around the New England Aquarium, or browse the city's shops, galleries, and museums.

You will start the day with a guided walk along the Freedom Trail, taking in the city's iconic sights and gaining an insight into its fascinating history. You have the rest of the day at leisure — you may wish to visit Boston Common, Faneuil Hall, Quincy Market, the red-brick houses of Beacon Hill or the world-famous Harvard University over the river in Cambridge.

Today, you will pick up your rental car. A gentle two-hour drive north takes you through the New England countryside to the coastal town of Kennebunkport, perched on Maine's rocky Atlantic coastline. Your afternoon is free to relax on the beach or explore this pretty coastal town's galleries and craft shops.

Today's two-and-a-half-hour drive takes you inland, the road weaving its way through New Hampshire's Lakes Region to the picture-postcard town of Jackson. The traditional town comes complete with a wooden covered bridge and white clapboard houses and is located in the heart of the White Mountains National Forest. There are many scenic walks and drives to enjoy in the surrounding area, or you can relax in your hotel while taking in the beautiful mountain scenery.

This morning, you will make your way to North Conway, where you will enjoy a train journey on an authentic cog railway up to Mount Washington's summit, the region's highest peak. You have the rest of the day at leisure to explore New Hampshire's White Mountains. This rugged region is a paradise for hikers, allowing an opportunity to sample the Appalachian Trail that stretches from Maine to Georgia. If you'd prefer to enjoy the panorama from the comfort of your car, we can recommend some excellent scenic drives that weave their way through the mountains.

Continue your journey southwest into Vermont — a particularly scenic drive along the Kancamagus Highway mountain road which is frequently rated as one of America's best scenic byways. Allow yourself plenty of time to stop at the numerous scenic viewpoints, and if you're lucky, you may even see moose meandering across the road, so ensure you have your camera on hand. This breathtaking drive takes you across the state border into Vermont and to the incredibly scenic Green Mountains. The rest of the day is free to explore Manchester's rolling hills and pretty villages.

A day at leisure to enjoy Vermont's Green Mountains. Take a scenic drive around some of the little towns here, or enjoy some easy hiking in the nearby hills. For those interested in history, Abraham Lincoln's family home at Hildene is just a short drive away, and shoppers are able to pick up bargains at Manchester's small selection of outlet stores.

Today's five-hour drive south brings you back to the coast and to the upmarket maritime town of Newport, Rhode Island. Be sure to visit one of the town's extravagant Gilded Age mansions, which were built in the late 19th century as summer homes for New York's wealthiest families.

Spend the day at leisure in the City by the Sea. You may wish to explore Newport's historic mansions for an insight into America's wealthiest families from the Gilded Age. Movie buffs will enjoy visiting Rosecliff, the house in Robert Redford's 1974 adaptation of The Great Gatsby.

An easy drive east takes you to Cape Cod, where your afternoon is free to relax on a beach, explore coastal villages or go whale watching — humpback, finback and minke whales migrate to these waters to feed between April and October.

Spend the day at leisure on Cape Cod. We recommend visiting Provincetown at the very tip of the Cape to enjoy the vibrant arts scene around Commercial Street.

One more day at leisure to enjoy the views as the Atlantic Ocean crashes onto this beautiful coastline, strewn with quaint harbours, windswept beaches, golden dunes and romantic lighthouses. It's worth making the trip up to Provincetown, known as one of America's premier whale-watching destinations, or you may wish to take the short ferry ride over to the islands of Martha's Vineyard or Nantucket. Your specialist will be able to provide more details on ferry tickets, schedules and whale-watching trips.

Return to Boston today to end your New England journey. During the two-hour journey, if your flight departs this evening, we recommend stopping at Plymouth, renowned as the landing point of the Pilgrim Fathers, who arrived in the New World on the Mayflower in 1620. You could also pay a visit to Pilgrim Hall Museum, which is the oldest continuous museum in the USA and has a collection of pilgrim artifacts. Plimoth Patuxet Museum is a well-established living history museum. Exhibits depict the lives of the Wampanoag community, who have lived in the region for thousands of years, and the 17th-century pilgrims who settled here. A superb reconstruction of the original ship, the Mayflower II, is not far away, which you can visit using your Plimoth Patuxet Museums ticket. Arriving in Boston, return your car before boarding your onward flight.

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The perfect New England fall-foliage road trip for 2023

Oct 2, 2023 • 7 min read

On this 424-mile drive through New England, the foliage will dazzle © Chun Chen / 500px / Getty Images

Touring New England in search of autumn’s changing colors has become so popular it has grenerated its own subculture of “leaf-peepers.”

While admiring the leaves during foliage season is possible everywhere in the the region, here’s one road trip that will immerse you in the best of those glorious colors.

New England’s best fall-foliage road trip

Trip length : 5– 7 days; 424 miles (682km) Best time to go : Late September to mid-October Essential photo : Kent Falls set against a backdrop of autumnal colors Top experience : Zip-lining through the tree canopy in Bretton Woods

Scarlet and sugar maples, ashes, birches, beeches, dogwoods, tulip trees, oaks and sassafras all contribute to the carnival of autumn color in New England. But this trip is about much more than just flora and fauna: expect to embrace the harvest spirit makes at family outings at pick-your-own farms, leisurely walks along dappled trails and tables groaning beneath delicious seasonal produce.

1. Lake Candlewood, Connecticut 

With a surface area of 8.4 sq miles, Candlewood is the largest lake in  Connecticut . On its western shore,  Squantz Pond State Park is popular with leaf-peepers who come to amble along the pretty shoreline. In Brookfield and Sherman, quiet vineyards with acres of gnarled grapevines line the hillsides; at  White Silo Farm Winery , the focus is on specialty wines made from farm-grown fruit. For the ultimate bird’s-eye view of the foliage, consider a late afternoon hot-air balloon ride with GONE Ballooning  in nearby Southbury.

The drive: From Danbury at the southern tip of the lake, you have a choice of heading north via US 7, taking in Brookfield and New Milford (or trailing the scenic eastern shoreline along Candlewood Lake Rd S); or heading north along CT 37 and CT 39 via New Fairfield, Squantz Pond and Sherman, before reconnecting with US 7 to Kent.

2. Kent,  Connecticut

Picturesque Kent ranks among the top spots for fall foliage in all of New England. Situated in the Litchfield Hills on the banks of the Housatonic River, the village is surrounded by dense woodlands. For a sweeping view, hike up Cobble Mountain in Macedonia Brook State Park , a wooded oasis two miles north of town. The steep climb to the rocky ridge affords panoramic views of the foliage against a backdrop of the Taconic and Catskill mountain ranges.

The 2175-mile (3500km) Georgia-to-Maine  Appalachian National Scenic Trail  also runs through Kent and up to Salisbury, on the Massachusetts  border. Unlike much of the trail, the Kent section offers a mostly flat five-mile walk alongside the Housatonic, the longest river walk of the entire trail. The trailhead is accessed on River Rd, off CT 341.

The drive:  The 15-mile drive from Kent to Housatonic Meadows State Park along US 7 is one of the most scenic drives in Connecticut. The single-lane road dips and weaves between thick forests, past Kent Falls State Park  (with its tumbling waterfall, visible from the road) and over West Cornwall’s picturesque covered bridge, which spans the Housatonic.

3. Housatonic Meadows State Park, Connecticut

During the spring thaw, the churning waters of the Housatonic challenge kayakers and canoers. By summer, the scenic waterway transforms into a lazy, flat river perfect for fly-fishing. In the Housatonic Meadows State Park, campers vie for a spot on the banks of the river while hikers take to the hills on the Appalachian Trail. Housatonic River Outfitters runs guided fishing trips with gourmet picnics.

Popular with artists and photographers, one of the most photographed fall spots is the Cornwall Bridge (West Cornwall), an antique span that stretches across the broad river, framed by vibrantly colored foliage.

The drive:  Continue north along US 7 toward the Massachusetts border and Great Barrington. After a few miles, you’ll leave the forested slopes of the park behind you and enter expansive rolling countryside dotted with large red-and-white barns. Look out for hand-painted signs advertising farm produce – and consider stopping overnight in Falls Village, which has an excellent B&B.

4. The Berkshires,  Massachusetts

Blanketing the westernmost part of Massachusetts, the rounded mountains of the Berkshires turn crimson and gold as early as mid-September. The effective capital of the Berkshires is Great Barrington, a formerly industrial town whose streets are now lined with art galleries and upscale restaurants.

It’s the perfect place to pack your picnic or rest your legs before or after a hike in the nearby Beartown State Forest . Crisscrossing its 12,000 acres, hiking trails yield spectacular views of wooded hillsides and pretty Benedict Pond. Further north, October Mountain State Forest is the state’s largest tract of green space (16,127 acres), also with ample hiking trails. The name – attributed to Herman Melville – gives a good indication of when this park is at its loveliest, with its multicolored tapestry of hemlocks, birches and oaks.

The drive:  Drive north on US 7, the spine of the Berkshires, cruising through Great Barrington and Stockbridge. In Lee, the highway merges with scenic US 20, from where you can access October Mtn. Continue 16 miles north through Lenox and Pittsfield to Lanesborough. Turn right on N Main St and follow the signs to the park entrance.

5. Mt Greylock State Forest,  Massachusetts

Massachusetts’ highest peak is not so high (only 3491ft / 1064m) – yet a climb up the 92ft-high War Veterans Memorial Tower rewards you with a forested panorama stretching up to 100 miles across the Taconic, Housatonic and Catskill ranges and over five states. Even if the weather seems drab, driving up to the summit may well lift you above the gray blanket, and the view with a layer of cloud floating between tree line and sky is simply magical.

Mt Greylock State Reservation has some 45 miles of hiking trails, including a portion of the Appalachian Trail. Frequent trail pull-offs on the road up – including some that lead to waterfalls – make it easy to get at least a little hiking in before reaching the summit.

The drive:  Return to US 7 and continue north through the quintessential college town of Williamstown. Cross the Vermont border and continue north through the historic village of Bennington. Just north of Bennington, turn left on Rte 7A and continue north to Manchester.

6. Manchester, Vermont

Stylish Manchester is known for its charming architecture. For fall-foliage views, head south of the center to 3828ft-high  Mt Equinox , the highest mountain accessible by car in the Taconic Range. Wind up the 5.2 miles – with gasp-inducing scenery at every hairpin turn – seemingly to the top of the world, where the 360-degree panorama unfolds, offering views of the Adirondacks , the lush Battenkill Valley and even Montréal ’s Mt Royal . 

If early snow makes Mt Equinox inaccessible, visit 412-acre Hildene , a Georgian Revival mansion once home to the Lincoln family. It’s filled with presidential memorabilia and sits nestled at the edge of the Green Mountains, with access to eight miles of wooded walking trails.

The drive:  Take US 7 north to Burlington. Three miles past Middlebury in New Haven, stop off at Lincoln Peak Vineyard for wine tasting or a picnic lunch on the wraparound porch.

7. Lake Champlain, Vermont

With a surface area of 490 sq miles and straddling  New York , Vermont and  Québec , Lake Champlain is the largest freshwater lake in the US after the  Great Lakes . On its northeastern side, Burlington is a gorgeous base from which enjoy the lake. Explore the lively city by foot, then scoot down to the wooden waterfront promenade, take a swing on the four-person rocking benches and consider a bike ride along the 7.5-mile lakeside path.

For the best off-shore foliage views, we love the  Friend Ship sailboat at  Whistling Man Schooner Company , a 43ft-sloop that accommodates a mere 13 passengers. Next door, ECHO Lake Aquarium & Science Center explores the history and ecosystem of the lake, including a famous snapshot of Champ, Lake Champlain’s mythical sea creature.

The drive:  Take I-89 southeast to Montpelier, passing  Camels Hump State Park and  CC Putnam State Forest . At Montpelier, pick up US 2 heading east to St Johnsbury, where you can hop on I-91 south to I-93 south. Just after Littleton, take US 302 east to Bretton Woods.

8. Bretton Woods, New Hampshire

Unbuckle your seat belts and step away from the car. You’re not just peeping at leaves today: you’ll be swooping past them on zip lines that drop 1000ft at 30mph. The four-season Bretton Woods Canopy Tour includes a hike through the woods, a stroll over sky bridges and a swoosh down 10 cables to tree platforms.

If this leaves you craving even higher views, cross US 302 and drive six miles on Base Rd to the coal-burning, steam-powered Mount Washington Cog Railway  at the western base of Mt Washington , the highest peak in New England. This historic railway has been hauling sightseers to the mountain’s 6288ft (1916m) summit since 1869.

The drive:  Continue driving east on US 302, a route that parallels the Saco River and the Conway Scenic Railroad, traversing Crawford Notch State Park . At the junction of NH 16 and US 302, continue east on US 302 into North Conway.

9. North Conway, New Hampshire

Many of the best restaurants, pubs and inns in North Conway come with expansive views of the nearby mountains, making it an ideal place to wrap up a fall-foliage road trip. If you’re traveling with kids or skipped the cog railway ride up Mt Washington, consider an excursion on the antique Valley Train with the Conway Scenic Railroad , a short but sweet round-trip ride through the Mt Washington Valley from North Conway to Conway, 11 miles south. The Moat Mountains and the Saco River will be your scenic backdrop. First-class seats are usually in a restored Pullman observation car.

This article was first published Sep 3, 2019 and updated Oct 2, 2023.

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9 places to nosh on bagels in southern Maine

From old-school spots to foodie favorites, there's a 'hole' lot to try.

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Bread and bagels at The Works Cafe in downtown Portland. Photo by Aimsel Ponti

From New York-style boiled bagels to Montreal-inspired wood-fired ones, there’s lots of great bagels in southern Maine and several shops have the accolades to back that up.

In 2023, Bon Appetit named bagels from Rose Foods and Rover Bagel among the best in the country.

Two years before that,  Food & Wine Magazine put Rover, Forage and Scratch Baking Co. on its list of best bagels in the U.S.

Whether you like yours toasted with cream cheese or as the bread for your breakfast sandwich, you can find plenty of styles and flavors from Biddeford to Brunswick.

BEACH BAGELS

The offerings at Beach Bagels include a French toast and marble bagel, and the cream cheese menu comprises spreads like strawberry, olive and honey walnut. Along with breakfast sandwiches, Beach Bagels has hearty breakfast options like omelets and pancakes. Best of all, you’re steps away from a beach stroll. Just don’t let the seagulls steal your bagel. Advertisement

WHEN: 7 a.m. to 3 p.m. daily WHERE: 34 Old Orchard St., Old Orchard Beach. beachbagels.yolasite.com ______________

Dutchman’s opened in 2022 as a pop-up housed at Nomad pizza in Brunswick’s Fort Andross building. It’s since become a permanent fixture there and uses the pizzeria’s wood-fired ovens to bake its bagels. The hand-shaped, honey-boiled bagels come in plain, roasted garlic, poppy and a bagel-of-the-day flavor.

WHEN: 8 a.m. to 1 p.m. Thursday to Sunday WHERE: Fort Andross, 14 Maine St., Brunswick. dutchmans.me ______________

FORAGE MARKET

Making bagels at Forage Market involves a two-day aging process. The bagels are naturally leavened with wild yeast starter and baked next to a hardwood fire. There are usually five flavors available, including sesame and garlic. Breakfast sandwiches (including vegan options) are available. Forage also has a location in Lewiston. Advertisement

WHEN: 7 a.m. to 1 p.m. Monday to Friday, 8 a.m. to 1 p.m. Saturday and Sunday WHERE: 123 Washington Ave., Portland. foragemarket.com _____________

MISTER BAGEL

There are 10 or so Mister Bagel locations in Maine, including South Portland and Falmouth. It all began with the Portland location, which was the first bagel shop to open in Maine. The late Rick Hartglass started Mister Bagel in 1977, and it is still a family business. Music fans will appreciate the breakfast sandwich menu, which includes The David Bowie (bacon, egg and American cheese), the Jimmy Buffett (egg with roast beef and cheddar) and The Lady Gaga (avocado, salt and pepper, with or without egg).

WHEN: 6:30 a.m. to noon Monday to Friday, 7 a.m. to noon Saturday and Sunday WHERE: 599 Forest Ave., Portland. misterbagelforestave.com ______________

At Rose Foods, the menu varies depending on the day, but there are usually six to eight flavors available. For example, should you pop in on a Friday, you’ll find a poppy and onion bialy (a cousin of the bagel that is not boiled). Rose Foods also makes a number of bagel sandwiches, including the Classic Nova with Nova lox and the Classic Whitefish. Advertisement

WHEN: 7 a.m. to 2 p.m. daily WHERE: 428 Forest Ave., Portland. rosefoods.me

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ROVER BAGEL

At Rover Bagel, you’ll find wood-fired plain, poppy, sea salt, sesame and everything bagels available most of the time, and the spread game here is strong with cream cheese options like lemon-thyme-honey cream and chili-garlic.

WHEN: 7 a.m. to 1 p.m. Wednesday to Friday, 8 a.m. to 1 p.m. Saturday, 8 a.m. to noon Sunday WHERE: 10 West Point Lane Suite 10-204, Biddeford (Pepperell Mill). roverbagel.com

______________ Advertisement

SCRATCH BAKING CO.

You haven’t lived until you’ve experienced the line of devoted fans waiting for Scratch Baking Co. to open, especially on weekend mornings. Along with the popular Maine sea salt, plain and other everyday flavors, Scratch has a daily special bagel. There’s honeyed rosemary on Wednesday and jalapeno cheddar on Thursday. Scratch is also famous, at least to locals, for its P-Cheese spread. It’s a pimento cheese recipe made with cheddar, mayo, roasted red peppers and seasoning and was passed down to co-owner and head baker Allison Reid by her grandmother, Mern.

WHEN: 7 a.m. to 1 p.m. Wednesday to Saturday, 7 a.m. to noon Sunday WHERE: 416 Preble St., South Portland. scratchbakingco.com ___________

THE MAINE BAGEL

The Maine Bagel is a drive-thru with several breakfast and other kinds of sandwiches available. With a bagel list that features egg and bialy among the standards, the family-owned spot is the perfect place to stop on your way to Pine Point Beach. The Maine Bagel really shines with a dozen kinds of cream cheese spreads, including raisin-walnut, lox, strawberry, cranberry-nut and bacon-chive.

WHEN: 6:30 a.m. to 2 p.m. Tuesday to Friday, 7 a.m. to 1 p.m. Saturday. WHERE: 117 Route 1, Scarborough. themainebagel.com Advertisement

THE WORKS CAFE

The Works Cafe is an institution on the edge of the Portland’s Old Port. It opened in 1990 as Bagel Works before it changed its name in 2002. The original shop in this regional chain opened in Manchester, Vermont, in 1988, and there are 11 locations around New England, though just the one in Maine. Gone are the ’90s-era banana-walnut bagels and cold pizza cream cheese, but The Works Cafe is still a reliable place to grab a salt, multigrain or cinnamon raisin bagel, among others. The menu also has bowls, sandwiches and smoothies.

WHEN: 6 a.m. to 7 p.m. daily WHERE: 15 Temple St., Portland. workscafe.com

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