gloucester ma walking tour

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Gloucester Harbor Walk to Cape Ann

This free and self-guided interactive virtual and on-the-ground tour overlaps the Gloucester Harbortown Cultural District and the Historic District as well as the Essex Coastal Scenic Byway. It stretches over a mile and encompasses much of our City’s unique and authentic heritage on over forty granite posts. It was designed to appeal to visitors of every age and interest with numerous links to more information  with some wonderful video clips and an acclaimed Walking cinema from unTravel Media .It also has an introduction to poets Charles Olson and T.S. Eliot;  artist and writer, Virginia Lee Burton; and women workers on the waterfront.

The Walk was facilitated by the City of Gloucester with support from the Seaport Advisory Council. It was designed by Cambridge Seven Associates and includes interactive components. Among other awards, its Walking Cinema took the Gold MUSE of the American Alliance of Museums ahead of the Smithsonian’s American History Museum and the Barnes Foundation.  The Walk also won the Excellence on the Waterfront award and much press. Please see the website, http://gloucester.harborwalk.org

Rocky Neck Historic Art Trail

Map and Walking Tour

Visit the location that has inspired exceptional artistic achievement for more than 150 years!

The Rocky Neck Historic Art Trail takes you to fifteen sites of art historical significance in one of America’s most visually arresting locales. Rocky Neck is a granite promontory with tide flats and wharf buildings separating the harbor proper from Smith’s Cove in Gloucester, Massachusetts. With its scenic views and humble waterfront buildings, this spit of land measuring less than one square mile has since the early 19th century beckoned a steady stream of painters, sculptors and writers to its picturesque shores. Regarded by many to be “America’s Oldest Working Art Colony,” the artists’ enclave at Rocky Neck during the period from 1850 to 1950 attracted a number of the most important realist painters in the annals of American art.

By mapping the sites where they worked, lived and became inspired, the Rocky Neck Historic Art Trail enables you to walk in the footsteps of Winslow Homer, Fitz Henry Lane, Augustus Buhler, Frank Duveneck, Marsden Hartley, Edward Hopper and a host of other pioneering American artists, and to see first-hand the iconic land and seascapes that gave rise to their illustrious artistic output. It is hoped that, by enabling you to identify where historical artistic events took place and to see them in the context of what remains today, the Trail documents will ensure you make the most of your visit to one of the special places in the history of American art.

Marsden Hartley (1877-1943), Summer Outward Bound , (detail) Gloucester, 1931, oil on board, Cape Ann Museum, bequest of Robert L. French, 2009.

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The Most Delicious Way to Discover Cape Ann.

Our food-focused tours will leave you with a full belly and a true understanding of what makes this charming area of New England so unique.

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Gloucester, MA

Our most filling tour, guests will make their way on foot through downtown Gloucester. From chowder, to olive oil, to a sandwich that Gloucester natives have been enjoying for decades, this tour will expose you to local treats you’d be hard pressed to discover on your own. Learn more »

Newburyport, MA

There are ways to experience Newburyport, MA. however, none are as fun or as satisfying as our Taste Newburyport food and cultural tour. You’ll get a true sense of this charming New England city as we make our way on foot through downtown Newburyport sampling food from local vendors.  Learn more »

Grab a drink, pull up a chair and listen to the tales of those who have made their living off the fierce ocean of the North Atlantic. Ales and Tales visits two local watering holes where you are immersed in the harrowing tales of those that have gone down to the sea in ships. Learn more »

ABOUT OUR CULINARY & CULTURAL TOURS

Cape Ann Foodie Tours are walking culinary and cultural tours of Cape Ann Massachusetts. Our tours will show you a side of Cape Ann you would have been hard pressed to find on your own.

Our food-focused tours will leave you with a full belly and a true understanding of what makes this charming area of New England so unique. From our premier “Taste Gloucester” walking tour of America’s oldest working seaport, to our “Ales and Tales Tour”, and our “Newburyport Food Tour” we are sure to have something to suit every appetite. We truly believe there is no better way to discover a city and soak in the local culture than by indulging in its food, so join us today for an authentic Cape Ann Foodie experience!

What people are saying…

”Do you enjoy … exploring a town that is new to you or maybe it’s a old friend you haven’t visited in awhile. Newburyport is a very [...]”

History, Humor,Adventure and Foodie Treats

”I had family visiting in July and had the honor of spending the weekdays with them while my dad was at work. As a Cape Ann local, [...]”

“Everything we wanted and more!”

”Cindy and this tour were wonderful!! We had a great time and did not leave Gloucester hungry – Cindy had excellent recommendations, and shared tons of interesting [...]”

“Great Way to Explore Gloucester!”

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Cape Ann Harbor Tour: Self-Guided Drive

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Welcome to the cape ann harbor tour.

Discover Cape Ann with a self-guided drive along the scenic waterfront! Enjoy the vistas, beaches, and natural beauty of this quintessential New England coastline at your own pace. Visit the famous Fisherman’s Memorial, beautiful Beauport, and the scenic Harborwalk, all while diving into the stories of Massachusetts of days past. The roundtrip tour through Gloucester and Rockport also visits Fort Point, Eastern Point Lighthouse, Bearskin Neck, Halibut Point State Park, and more .

About the Tour

Cruise along the road less traveled on Cape Ann, where adorable villages, stunning beaches, and history dating back hundreds of years come together. On this flexible, app-based tour, you can move at your own pace and stop for photos wherever you’d like!

The tour begins just outside Gloucester, with gorgeous views of the harbor. Here, you’ll find the enormous Tablet Rock, which opens a window to the year 1623, when Pilgrims first landed on these shores. Hear all about their struggles to survive in this harsh new land.

Next, head into Gloucester and dive into the town’s uniquely New England culture. Learn about the importance of fishing to this community, the dangers of that high-stakes profession, and the tragic story behind the Perfect Storm, which still reverberates through this town to this day.

Then, visit Gloucester’s harbor to see why locals simply can’t live anywhere but here. Meander along the gorgeous harborwalk, breathe in the salty sea air, and maybe even spot a few whales!

After that, cruise along with the cape’s artsy southern point and discover the artist colony of Rocky Neck and the spectacular Niles Beach, perfect for catching some sun. Admire the huge, 56-room mansion of Beauport, then snap some iconic Massachusetts photographs of the Eastern Point Lighthouse.

Drive-up the eastern coastline next on your Cape Ann Harbor tour, past plenty of spotless beaches, including the unbelievably picturesque Pebble Beach, which feels like it was practically made for Instagrammable moments! Listen to the tale of Thacher Island just beyond the shore and the shipwreck which put it on the map.

Then, head through Rockport and hear the wild story of Hatchet Hannah and her crusade against alcohol. After picking up on the local history, you’ll get the chance to see the most painted building in the entire world. No, really!

Venture north to the most remote part of the cape, and listen along the way to the harrowing events of the infamous Blizzard of 1978 and another equally terrible storm over a century earlier. Then, stretch your legs in the beautiful Halibut Point State Park, which offers breathtaking ocean views you can’t find just anywhere.

Finally, angle back toward Gloucester, but not without getting the inside scoop on the so-called Witch House and the devastating shipwrecks that have occurred along this cape over the years. This comprehensive, self-guided driving tour will show you everything there is to see on the Cape Ann Harbor tour and fill you in on all the stories you need to hear while you’re at it!

Starting Point Address: Glouchester Visitor Center at Stage Fort Park, 24 Hough Ave, Gloucester, MA 01930

See the Best of Massachusetts:

See all the top sights in Massachusetts at your own pace with our Self-Guided Driving and Walking Tour Bundle. Priced at just $39.99, the bundle gives you access to over 300+ audio stories and lets you in on never before heard stories.

How does it work?

• Once you book a tour, you’ll get a text/email with instructions.
• Download the app (while in good wifi/signal) and use your unique password to access your tours.
• To begin touring, go to the starting point and launch the app.
• The audio starts automatically once you reach the starting point. Stick to the tour route & speed limit for the best experience.
• Please note that no one will meet you at the starting point.

What You'll See

Our Cape Ann excursion begins at the Gloucester Visitor Information Center. We'll get our view breathtaking views of the waterfront from this point.

Walk to Scenic Views

Instead of setting off on our drive right away, we'll first check out the most striking feature of the scenery: the massive Tablet Rock. In 1907, the plaque the rock was unveiled to Commemorate the first settlers in this area.

Tablet Rock at Stage Fort Park

We can also choose to walk around this area before our driving, admiring the amazing views of the park, the ocean, and the city.

Fisherman’s Memorial

Our drive along Cape Ann's scenic harbor begins once we cross the canal. First, we'll admire Cape Ann's most famous momument: the Fisherman's Memorial. As we continue, we'll learn about the significance of fishing in Cape Ann's past — and the famous movie about it, "The Perfect Storm".

Gloucester HarborWalk

Here we can choose to pause again to explore Cape Ann's Harborwalk. Along the path are 41 granite slabs containing pieces of the town’s long, odd, sometimes sad history. These “story moments,” as they are called, were put together by teams of volunteers eager to show the world what Gloucester is made of. Taken together, they form a mosaic of this strange, beautiful place.

Cape Ann Whale Watch

Cape Ann and Glouchester’s whale watching industry guarantees whale sightings with every voyage. Their boats often take passengers to a marine wildlife preserve that’s been called one of the top five whale-watching destinations in the entire world!

Niles Beach

As we drive along scenic Cape Ann's waterfront, we'll discover beaches both big and small. We can choose to stop at one, some, or all, as we learn more about what's unique about each one.

Beauport, also known as Sleeper–McCann House, Little Beauport, or Henry Davis Sleeper House, is a beautiful historic home tucked away on the Cape Ann waterfront. As we drive, we'll dive back into Cape Ann's history.

Eastern Point Lighthouse

During the early 1800s, maritime trade in Gloucester was booming. Ships traveling between these ports and China or India were turning enormous profits, and captains started to become especially anxious at the prospect of losing their extremely valuable cargo in a shipwreck. Enter: lighthouses!

Thacher Island

Thacher Island is a small island off Cape Ann on the Massachusetts coast in the United States. It is a part of the Town of Rockport. It was a place where some naval confrontations, both minor and major, took place, which helped secure a victory for the colonists.

Our scenic drive along Cape Ann now leaves Gloucester and brings us into Rockport. We'll learn more about Rockport and the region as we drive.

Our brings us to "the most painted building in America"!

Bearskin Neck

This land was once home to a large number of bears, but don’t worry! They’re long gone now. According to legend, one such bear was caught by the tide and killed in 1700, which is how this place got its name.

Granite Pier

Granite Pier is one of the Rockport’s oldest piers. As you might have guessed, this used to be where ships would be loaded with granite for transport. As we explore the pier and nearby beaches, we'll get a better understanding of the Cape Ann of days past, and that of the present. Our drive then continues along Halibut Point and Harvey Reservation.

Annisquam Lighthouse

Annisquam Harbor Light Station is a historic lighthouse on Wigwam Point. As we approach, we'll learn more about shipwrecks, shipping, fishing, and maritime trade.

Goose Cove Reservation

Our scenic drive along Cape Ann has finally looped back to Stop 1! We're nearly back at the Gloucester Visitor Information Center.

Preview The Tour

  what is cape ann known for.

Cape Ann is known for its picturesque coastal scenery, charming towns, historic landmarks, vibrant arts community, and fishing heritage.

  Why is it called Cape Ann?

Cape Ann is named after Queen Anne of England, as a tribute to her. It was originally settled by European colonists in the early 1600s.

  Where is Cape Ann located?

Cape Ann is located on the northeastern coast of Massachusetts, in Essex County. It includes the towns of Gloucester, Rockport, Manchester-by-the-Sea, and Essex.

  Why do people go to Cape Ann?

People visit Cape Ann to enjoy its stunning beaches, explore art galleries and studios, experience maritime history, indulge in fresh seafood, and immerse themselves in the region’s natural beauty.

  Is Gloucester city worth visiting?

Yes, Gloucester is worth visiting for its historic seaport, beautiful harbor, vibrant arts scene, and cultural attractions like the Gloucester Maritime Heritage Center

  How do I spend a day in Gloucester?

Spend a day in Gloucester by exploring its historic district, visiting museums, enjoying fresh seafood, strolling along the harbor, and perhaps taking a whale watching tour.

  What is the difference between Cape Cod and Cape Ann?

Cape Cod and Cape Ann are both scenic coastal areas in Massachusetts, but Cape Ann is located farther north and is known for its rocky coastline, fishing heritage, and arts community.

  What towns are part of Cape Ann Massachusetts?

The towns that are part of Cape Ann are Gloucester, Rockport, Manchester-by-the-Sea, and Essex.

  What is the name of the most famous cape in Massachusetts?

The most famous cape in Massachusetts is Cape Cod, known for its iconic sandy beaches, charming villages, and vacation atmosphere.

  What are the 3 main capes?

The three main capes in Massachusetts are Cape Cod, Cape Ann, and Cape Elizabeth.

  Can I Bring My Car to Martha’s Vineyard?

Yes, you can bring your car to Martha’s Vineyard. There are car ferry services available to transport vehicles to the island

  Can I bring my pets on this self-guided tour?

It’s advisable to check with the specific tour organizers or locations regarding their policies on bringing pets, as some places may have restrictions or guidelines for pet access.

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Events Calendar

De Hirsh Margules, Mother Ann Lighthouse, Eastern Point, Gloucester , 1946. Gouache on paper. Gift of Jean M. Horblit, 2002. [Acc. #2002.004.002]

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April School Vacation Week: Earth Day Activities

Tuesday, April 16 – Friday, April 19, 2024 Downtown Campus, 27 Pleasant Street, Gloucester, MA Free for school-age children, 18 and under, and their guardians  Celebrate the return of spring […]

Daily Docent-led Highlights Tours: Tuesday-Saturday at 11am

Tuesdays-Saturdays at 11am  Downtown Campus, 27 Pleasant Street, Gloucester MA  Free with admission  Wondering where to start your visit? Wanting to learn more about Museum pieces? Explore the galleries and […]

Gallery Tour – In the Round: 20th Century Cape Ann Sculpture

with Leon Doucette, Assistant Curator Thursdays at 2:00 pm from April 11 – June 20, 2024 Downtown Campus, 27 Pleasant Street, Gloucester, MA Registration required for all attendees. Free with […]

CAM Studio Course: Introduction to Oil Painting with Water Soluble Oils

with Melody Phaneuf Thursdays from 6:00 pm - 8:00 pm 6 weeks from April 11 – May 16, 2024 CAM Green, 13 Poplar Street, Gloucester, MA $225 for CAM Members, […]

CAM Studio Course: Block Printing Colors with Mary Rhinelander

Fridays from 10:00 am - 12:30 pm 6 weeks from April 5 – May 17, 2024 No class on April 26 CAM Studio, 27 Pleasant Street, Gloucester, MA $260 for […]

CAM Studio Weekly Workshop: Friday Figure Drawing with Live Model

Pay at the Door (cash only) Fridays from 1:00-4:00 pm starting December 1, 2023 No Session December 22 Janet & William Ellery James Center at CAM Green 13 Poplar Street, […]

Captain Elias Davis House Tour

Downtown Campus, 27 Pleasant St, Gloucester, MA Free with admission The Captain Elias Davis House, located in Gloucester’s downtown neighborhood, was constructed between 1799 and 1804 and has been the […]

Wetu & the White Ellery House

Saturday, April 20, 2024 at 10:30 am and at 12:00 pm CAM Green, 13 Poplar Street, Gloucester, MA Free and open to the public, registration required  Visit the Cape Ann […]

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The Wild Trek

40+ Best Things To Do In Gloucester Massachusetts

Looking for the absolute best things to do in Gloucester Massachusetts? Known as “America’s Oldest Seaport,” Gloucester is an incredible town with so many wonderful activities, and today we’re sharing our favorites!

Gloucester Massachusetts is located on Cape Ann and has been one of the top fishing towns in New England for basically ever. It’s a premier summer destination (especially if you like fresh seafood!) but there are lovely parts of Gloucester any time of year.

With its rich history, stunning natural beauty, and thriving arts scene, Gloucester offers a wide range of activities and attractions for visitors to enjoy. Whether you’re interested in exploring the city’s maritime heritage, immersing yourself in the arts, or simply enjoying the picturesque landscapes, Gloucester has something to offer for everyone. It’s one of the cutest small towns in Massachusetts for a reason!

Here are some of our absolute favorite things to do in Gloucester Massachusetts!

35. Visit Gloucester Harbor:

Start your journey in Gloucester by exploring its iconic harbor, which serves as a hub of maritime activity. Stroll along the waterfront, watch fishing boats come and go, and enjoy the fresh ocean breeze. Take a boat tour or a harbor cruise to get a closer look at the city’s seafaring traditions.

The harbor is such a gorgeous place to hang out! I like to sit here with my coffee in the mornings and watch as the seaside activities begin.

34. Discover Maritime History at the Gloucester Maritime Heritage Center:

Immerse yourself in Gloucester’s seafaring past at the Gloucester Maritime Heritage Center . Learn about the city’s history as a major fishing port, explore exhibits on boatbuilding and navigation, and see artifacts from Gloucester’s fishing industry.

This is a small center but totally worth a visit if you want to get a true feel for small-town Gloucester! This is one of the best things to do in Gloucester for history buffs and is a must-do.

33. Explore Rocky Neck Art Colony:

Known as one of America’s oldest continuously operating art colonies , Rocky Neck is a vibrant neighborhood that is home to numerous art galleries, studios, and shops. Take a leisurely walk along the streets, browse unique artworks, and engage with local artists. If you want a taste of New England art then this is the place to come!

32. Visit Cape Ann Museum:

Delve into the rich history and culture of Cape Ann at the Cape Ann Museum . Discover exhibits on the area’s art, history, and maritime heritage, including the famous Gloucester Fisherman’s Memorial Statue.

With a diverse collection of artwork, including paintings, sculptures, and photographs , the museum celebrates the region’s vibrant artistic community and highlights the contributions of renowned artists associated with Cape Ann.

Its exhibits explore topics such as the area’s maritime history, the fishing industry, and the lives and works of influential artists.

31. Relax on Good Harbor Beach:

Gloucester boasts several picturesque beaches, and Good Harbor Beach is one of the most popular. Enjoy a day of sunbathing, swimming, and beachcombing on its pristine shores. The beach is also known for its stunning sunsets.

Good Harbor Beach offers ample space for sunbathing, picnicking, and playing beach games.

Good Harbor Beach is also favored for its clear and inviting waters, making it an ideal spot for swimming and boogie boarding. Lifeguards are on duty during the summer months.

Whether you’re looking to relax under the sun, take a refreshing dip in the ocean, or simply enjoy the natural beauty of the New England coastline, Good Harbor Beach offers a quintessential beach experience that captivates visitors year-round. It’s one of the best well-known beaches in the area!

30. Take a Whale Watching Tour:

Gloucester offers fantastic opportunities for whale watching due to its proximity to Stellwagen Bank National Marine Sanctuary , a prime feeding ground for whales. Hop on a whale-watching tour and witness these magnificent creatures up close.

29. Visit Hammond Castle:

Step back in time at the Hammond Castle Museum , a medieval-style castle built in the 1920s by inventor John Hays Hammond Jr. Explore the castle’s unique architecture, marvel at its collection of medieval artifacts, and enjoy panoramic views of the ocean from its towers.

28. Rent a Boat at Gloucester Boat Rental:

Explore the scenic coastline and enjoy the freedom of the open water by renting a boat from Gloucester Boat Rental . Whether you prefer a powerboat, sailboat, or kayak, you can embark on your own maritime adventure and discover hidden coves and charming islands.

27. Check out Cape Ann Marina, Home of the Wicked Tuna Fishermen:

Visit Cape Ann Marina , known for being a hub of activity for the fishermen featured on the TV show “Wicked Tuna.” Watch the fishing boats come and go, learn about the local fishing industry, and maybe even spot some of the famous tuna fishermen.

You can also grab lunch at the Mile Marker , a delicious waterfront restaurant with a lively atmosphere that overlooks the marina.

26. Tour Beauport, the Sleeper-McCann House:

Explore the historic Beauport, the Sleeper-McCann House , a beautifully preserved mansion known for its eclectic architectural styles and stunning views of Gloucester Harbor. Take a guided tour to discover the fascinating history and unique design of this remarkable house.

25. Hike in Ravenswood Park:

Nature enthusiasts will appreciate the beauty of Ravenswood Park , a 600-acre nature reserve with miles of scenic trails. Enjoy a peaceful walk through wooded areas, along babbling brooks, and around tranquil ponds. Keep an eye out for wildlife and diverse plant species.

24. Attend a Performance at Gloucester Stage Company:

Experience the vibrant performing arts scene in Gloucester by catching a play at the Gloucester Stage Company . Known for its high-quality productions, this theater company showcases a diverse range of theatrical works throughout the year.

23. Explore Dogtown Common:

Dogtown Common is a fascinating area in Gloucester that was once a settlement in the 17th and 18th centuries. Today, it is a wooded landscape with hiking trails that lead to the remnants of old cellar holes and eerie stone structures. It offers a unique blend of history and natural beauty.

22. Grab Dinner at the Beauport Hotel:

Treat yourself to a delicious meal at the Beauport Hotel’s restaurant . Enjoy waterfront dining with panoramic views of the Atlantic Ocean while indulging in a delectable menu featuring fresh seafood and other culinary delights.

21. Stroll Through Downtown Gloucester:

Take a leisurely stroll through downtown Gloucester and soak in the city’s vibrant atmosphere. Discover charming shops, art galleries, and boutiques along Main Street . Enjoy a cup of coffee at a local café, browse unique treasures, and immerse yourself in the local culture.

20. Visit the Eastern Point Lighthouse:

Make your way to the Eastern Point Lighthouse , a historic landmark perched on the rocky shores of Gloucester. Take a guided tour or simply enjoy the breathtaking views of the Atlantic Ocean. The lighthouse offers a picturesque backdrop for memorable photographs.

19. Dine on Fresh Seafood:

Gloucester is renowned for its fresh seafood, and a visit to the city wouldn’t be complete without indulging in a delicious seafood meal. Whether you’re craving lobster, clam chowder, or freshly caught fish, you’ll find plenty of excellent seafood restaurants to satisfy your appetite. Here are some of our favorite seafood restaurants on the water:

1. The Gloucester House : Situated right on the waterfront, The Gloucester House offers not only stunning views of the harbor but also a fantastic dining experience. Enjoy fresh seafood dishes while watching the boats come and go.

2. The Lobster Pool : Nestled near Folly Cove, The Lobster Pool provides outdoor seating with panoramic ocean views. Savor their delicious lobster rolls and other seafood specialties while enjoying the coastal breeze.

3. Seaport Grille : Located in downtown Gloucester, Seaport Grille offers waterfront dining along the picturesque Harbor Loop. Indulge in their seafood-focused menu while taking in the scenic views of the harbor and boats passing by.

4. Mile Marker One : Situated at the Cape Ann’s Marina Resort, Mile Marker One features a waterfront patio where you can dine overlooking the Annisquam River. Their menu offers a wide range of options, including fresh seafood, burgers, and salads.

5. The Studio Restaurant : Positioned in the Rocky Neck Art Colony, The Studio Restaurant provides waterfront dining overlooking Smith Cove. Delight in their creative menu that combines seafood and international flavors.

18. Explore Stage Fort Park:

Discover Stage Fort Park , a scenic waterfront park with stunning views of Gloucester Harbor and the Atlantic Ocean. Enjoy a picnic, go for a walk along the promenade, and explore the historic remnants of the park’s fortifications, including the famous “Balance Rock.”

17. Take a Fishing Charter:

Embrace Gloucester’s fishing heritage by chartering a fishing boat and trying your hand at catching some fish . Whether you’re an experienced angler or a beginner, the local fishing charters offer a variety of trips to suit all skill levels.

16. Take a Sunset Dinner Cruise:

Treat yourself to a romantic and unforgettable experience by embarking on a sunset dinner cruise . Cruise along the coastline, savor a delicious meal and witness the stunning colors of the sky as the sun sets over the water. It’s a perfect way to celebrate a special occasion or create lasting memories.

15. Visit the Sargent House Museum:

Step inside the beautifully preserved Sargent House Museum , a Federal-style mansion built in 1782. Learn about the life and times of one of Gloucester’s prominent families through guided tours of the elegantly furnished rooms.

If you’re looking to get a real taste of Federalist history then this is the place to come!

14. Explore Halibut Point State Park:

Just a short drive from Gloucester, Halibut Point State Park offers breathtaking coastal scenery and picturesque walking trails. Explore the park’s rugged coastline, granite quarries, and enjoy panoramic views of the Atlantic Ocean.

13. Boat Watch at the Cut Bridge:

Find a spot near the Cut Bridge, also known as the Blynman Canal Bridge, and watch as boats pass through the opening. The bridge separates the Annisquam River from Gloucester Harbor and offers a unique vantage point to observe the comings and goings of various vessels, from small fishing boats to majestic yachts.

12. Attend the Gloucester Schooner Festival:

If you happen to visit Gloucester during the Labor Day weekend, don’t miss the Gloucester Schooner Festival. This annual event celebrates the city’s seafaring heritage and features a spectacular parade of schooners, maritime exhibits, live music, and fireworks.

11. Indulge in Art and Music Festivals:

Gloucester, Massachusetts, is a vibrant hub for art and music festivals, showcasing the region’s creative spirit and cultural diversity. The city hosts a variety of festivals throughout the year, attracting both local talent and renowned artists from around the world.

Art festivals like the Gloucester HarborWalk Public Art Challenge and the Cape Ann Artisans Studio Tour provide opportunities to explore and engage with the thriving art community, showcasing works in various mediums and styles.

Music festivals such as the Gloucester Blues Festival and the Rockport Jazz Festival bring the city alive with soulful tunes and captivating performances, drawing music enthusiasts from near and far.

10. Visit Essex Shipbuilding Museum:

Located nearby in Essex, the Essex Shipbuilding Museum is one of the coolest nautical museums in the area . Explore exhibits on traditional wooden boat construction, visit the museum’s working boatyard, and learn about the craft of shipbuilding.

Housed in a historic shipyard building, the museum offers visitors a glimpse into the traditional art of wooden boatbuilding.

The museum also features a working boatyard , where visitors can witness the process of boatbuilding firsthand and even participate in workshops. With its focus on preserving the seafaring traditions of Essex, the Essex Shipbuilding Museum provides an immersive and educational experience for all ages!

9. Explore the Backshore:

The Backshore is a rugged coastal area in Gloucester known for its beautiful rocky beaches and scenic landscapes. Take a leisurely drive along Atlantic Road and stop at spots like Bass Rocks and Good Harbor Beach to enjoy the dramatic ocean views.

8. Head to Wingaersheek Beach:

Located just a short drive from Gloucester, Wingaersheek Beach is a stunning sandy beach known for its tranquil waters and natural beauty . Spend a day relaxing on the beach, building sandcastles, or taking a refreshing swim. The beach also features a scenic walking trail along the marshland.

The beach is flanked by rocky outcrops that add to its scenic charm, and during low tide, visitors can explore tidal pools and check out the marine life.

Alternatively, you can take a boat to the backside of Wingaersheek Beach for a really packed, party atmosphere!

7. Go Kayaking or Stand-Up Paddleboarding:

Experience Gloucester’s coastline from a different perspective by renting a kayak or a stand-up paddleboard . Explore the calm waters, coves, and hidden corners of the city’s shoreline while enjoying a peaceful and active adventure.

6. Visit Nearby Rockport:

Looking to visit another quaint New England town? Check out Rockport Massachusetts, only a 5-10 minute drive from Gloucester. Rockport is one of the best towns for walking around, so we recommend heading here for an afternoon of fun. But it’s even gorgeous just to drive through!

Check out our favorite things to do in Rockport here.

5. Explore the Annisquam Village:

Venture into the charming Annisquam Village, a historic district within Gloucester. Admire the picturesque New England architecture, explore quaint shops and art galleries, and enjoy a leisurely stroll along the Annisquam River.

4. Visit the Gloucester Fishermen’s Wives Memorial:

Pay homage to the brave women of Gloucester’s fishing community by visiting the Gloucester Fishermen’s Wives Memorial . Located on Stacy Boulevard, this statue honors the resilience and strength of the women who have supported their families and loved ones in the fishing industry.

3. Attend the Gloucester Block Party:

If you happen to visit Gloucester during the summer, don’t miss the Gloucester Block Party.

This lively event takes place in downtown Gloucester and features live music, food vendors, local artisans, and family-friendly activities. It’s a great opportunity to immerse yourself in the local culture and enjoy a vibrant street festival atmosphere.

2. Go Fishing off the Breakwater:

Grab your fishing gear and cast a line off the breakwater, a long stone structure that extends into Gloucester Harbor.

This popular fishing spot offers opportunities to catch a variety of fish, from striped bass to bluefish, while enjoying panoramic views of the harbor.

1. Explore the Halibut Point Reservation:

Extend your adventure beyond Halibut Point State Park and explore the adjacent Halibut Point Reservation. This scenic coastal area features walking trails that wind through wooded areas and granite quarries, offering unique perspectives of the rugged shoreline and the surrounding ocean.

FAQs about visiting Gloucester Massachusetts:

What’s the best time of year to visit.

Personally, I would always visit in the summer. There are just  so many things to do in Gloucester Massachusetts in the summer! However, each season has its perks.

Spring (March to May): Spring brings milder temperatures to Gloucester, with average highs ranging from the 50s to 60s Fahrenheit (10-20 degrees Celsius). This season is ideal for exploring outdoor attractions, such as hiking in Ravenswood Park or enjoying the blossoming scenery. Spring is also a great time to visit if you prefer fewer crowds and lower accommodation rates.

Summer (June to August): Summer is a popular time to visit Gloucester, thanks to its pleasant temperatures ranging from the 70s to 80s Fahrenheit (20-30 degrees Celsius). It’s the perfect season for enjoying Gloucester’s beautiful beaches, going on boat tours, and participating in outdoor activities like whale watching. Keep in mind that summer is also the peak tourist season, so expect larger crowds and higher accommodation rates.

Fall (September to November): Fall in Gloucester is a stunning season, as the foliage transforms into vibrant shades of red, orange, and yellow. Temperatures gradually cool down, ranging from the 50s to 70s Fahrenheit (10-20 degrees Celsius), making it comfortable for outdoor exploration. Fall is a great time to enjoy scenic drives, visit local farms for apple picking, and experience the autumnal charm of Gloucester.

Winter (December to February): Winter in Gloucester brings colder temperatures, with average highs ranging from the 30s to 40s Fahrenheit (0-10 degrees Celsius). While it may be chilly, winter can be a magical time to visit Gloucester, especially if you enjoy cozy indoor activities. You can explore museums, enjoy seafood by the fireplace in local restaurants, or witness the winter beauty of the coastal landscapes.

What Are The Best Hotels In Gloucester Massachusetts?

Gloucester, Massachusetts offers a variety of accommodations to suit different preferences and budgets. Here are some of the best hotels in Gloucester:

1. Beauport Hotel Gloucester : Located on the waterfront, Beauport Hotel offers luxurious accommodations with stunning views of the ocean . The hotel features elegant rooms, an on-site restaurant, a rooftop pool, and easy access to the beach. It’s a top choice for those seeking a high-end and picturesque stay.

2. Bass Rocks Ocean Inn : Situated on the rocky shores of Gloucester, Bass Rocks Ocean Inn offers comfortable rooms with ocean views . The inn features a private beach, a heated outdoor pool, and a continental breakfast. It’s an ideal option for a peaceful and scenic getaway.

3. Vista Motel : The Vista Motel is a budget-friendly option that provides clean and comfortable rooms. It’s conveniently located near Good Harbor Beach and offers easy access to downtown Gloucester. The motel is known for its friendly service and affordability.

4. Atlantis Oceanfront Inn : Overlooking the Atlantic Ocean, Atlantis Oceanfront Inn offers spacious rooms with balconies and ocean views . The hotel features a private beach, a heated outdoor pool, and a complimentary breakfast. It’s a popular choice for those seeking a relaxing beachfront experience.

5. Castle Manor Inn : Housed in a historic building, Castle Manor Inn offers charming accommodations with modern amenities . The inn features cozy rooms, beautiful gardens, and a complimentary breakfast. It’s located a short distance from downtown Gloucester and offers a tranquil atmosphere.

6. The Inn at Babson Court : Set in a restored 1870s Victorian mansion, The Inn at Babson Court offers elegant rooms and a warm, welcoming ambiance. The inn features a garden, a wraparound porch, and a complimentary breakfast. It’s a popular choice for its historic charm and attentive service.

7. Cape Ann’s Marina Resort : Located on the Annisquam River, Cape Ann’s Marina Resort offers comfortable accommodations with scenic water views. The resort features an outdoor pool, a marina, and waterfront dining options. It’s a great choice for those interested in boating and water activities.

What’s The Best Way To Get To Gloucester?

By Car: If you have access to a car, driving to Gloucester is a convenient option. The city is located approximately 40 miles north of Boston, and the journey takes about an hour depending on traffic. Major highways such as Route 128 and Route 1A provide direct routes to Gloucester.

By Train: The MBTA Commuter Rail offers a convenient train service from Boston’s North Station to Gloucester. The Newburyport/Rockport Line connects Boston with Gloucester, and the journey takes about an hour. Trains run regularly throughout the day, providing a comfortable and scenic way to reach Gloucester.

By Bus: Several bus companies operate routes to Gloucester from various locations. Greyhound and Peter Pan Bus Lines offer service to Gloucester from Boston’s South Station, as well as other nearby cities. Bus travel times and schedules may vary, so it’s advisable to check the specific routes and timetables in advance.

By Air: If you’re coming from a more distant location, flying to a nearby airport is an option. The nearest major airport is Boston Logan International Airport (BOS), located approximately 35 miles away from Gloucester. From the airport, you can rent a car or take public transportation to reach Gloucester.

By Boat: Gloucester is a popular destination for boaters. If you have access to a private boat or yacht, you can sail into Gloucester Harbor and dock at one of the marinas or yacht clubs. The Cape Ann Marina and Gloucester Harbormaster’s Office can provide information on docking facilities and services. You’ll definitely want to make a reservation ahead of time – boat spaces fill up fast in the summer months.

What Are The Best Towns Near Gloucester Massachusetts?

Rockport: Just a short drive from Gloucester, Rockport is known for its quaint New England charm. The town features narrow streets lined with colorful buildings, art galleries, and specialty shops. Bearskin Neck, a bustling pedestrian area filled with boutiques and seafood restaurants, is a must-visit spot. Rockport’s picturesque harbor, Motif No. 1 (a famous fishing shack), and stunning coastal landscapes make it a popular destination for visitors seeking a delightful coastal retreat. There are just too many things to do in Rockport!

Essex : Located along the Essex River, the town of Essex exudes a charming small-town atmosphere. It is renowned for its historic shipbuilding heritage and is home to the Essex Shipbuilding Museum. Visitors can explore the town center’s antique shops, art galleries, and local eateries. Don’t miss out on trying fresh seafood at one of the renowned restaurants specializing in clam shacks and seafood joints.

Salem: Salem is a historic and enchanting town known for its rich history, witch trials, and maritime heritage. Explore the charming streets of downtown Salem, lined with beautiful historic homes and unique shops. Visit the Salem Witch Museum or the House of the Seven Gables to learn about the town’s infamous past. Discover the picturesque Salem Harbor, where you can enjoy waterfront dining, take a harbor cruise, or simply soak in the scenic beauty. Salem also offers a vibrant arts and culture scene, with numerous museums, galleries, and seasonal events that attract visitors from all over. Check out some of our favorite things to do in Salem here.

Manchester-by-the-Sea : Situated along the North Shore of Massachusetts, Manchester-by-the-Sea is a quaint coastal town with elegant architecture and stunning ocean views. Stroll along the tree-lined streets, admire the beautiful homes, and explore the charming downtown area with its unique shops and cafes. The town’s picturesque Singing Beach, known for its squeaky sand, is a favorite spot for locals and visitors alike.

Ipswich : With its rich colonial history and scenic beauty, Ipswich offers a delightful mix of historical charm and natural landscapes. Explore the well-preserved historic homes along High Street, visit the renowned Crane Estate and its breathtaking gardens, or take a stroll along Crane Beach, one of the most stunning beaches in the region. Ipswich is also known for its local clam shacks, where you can savor freshly caught seafood.

Newburyport : Located at the mouth of the Merrimack River, Newburyport is a charming coastal town with a vibrant downtown area. Its brick-lined streets are filled with boutique shops, art galleries, and restaurants. Visitors can enjoy waterfront views at the picturesque boardwalk, explore the historic district with its Federal-style homes, or take a boat cruise along the river. There are plenty of things to do in Newburyport during every season.

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