30+ Things To Do In Gloucester, MA

From dining on fresh seafood and wandering historic streets to relaxing on the beach or getting out on the water, there are endless things to do in Gloucester, MA. You’ll never run out of things to do in this North Shore town.

Historical street in Gloucester Mass
via Wangkun Jia on Shutterstock

Once a small fishing town, Gloucester is now one of the largest towns on the North Shore. Located on Massachusett’s Cape Ann, Gloucester has direct access to Boston via the Commuter Rail and is home to some of the best beaches on the North Shore.

But there’s so much more to this Cape Ann town than the beaches (though you should definitely check them out).

Below are 30 of the best things to do in Gloucester, with something for everyone no matter your interests.

The Best Things To Do In Gloucester

Go whale watching

The area just off Massachusett’s coast is populated by some truly incredible marine life. So what better way to take advantage of Gloucester’s beautiful New England surroundings than by going on a whale watching trip?

Not only can you enjoy a scenic boat ride and have an opportunity to spot some wildlife along the way, but you’re also able to learn more about whales. There will be a naturalist on board with the captain and crew, and you will receive guided commentary to teach your group about the animals.

This journey will take approximately four hours, and you are guaranteed to have sightings of the whales!

You can also sign up for a similar four-hour whale watching experience here. Prices start at $48 per person!

Take a self-guided driving tour

If you’d rather stick to land, but still want to explore what the Cape Ann area has to offer, a driving tour might be just what you’re looking for! Plus, if you go the self-guided route, you’ll get to enjoy the comfort and privacy of your own vehicle without sacrificing the insights that can only come from a narrated tour.

You can learn a great deal of local history and explore the beautiful lighthouses and quaint villages that line this part of the shore. Plus, since you will not be beholden to a structured tour, you can go at your own pace and stop to explore anything that catches your eye.

This experience starts at $14.99. The best part is that you only need to pay per car, instead of per person, which makes this a very affordable activity for any group.

Explore on electric bikes

If you don’t have a car available, or you’d like to explore with the wind on your face and no guide in your ear, electric bikes are the perfect option. You can rent a bike for the day and feel connected to the scenery that surrounds you as you ride around Cape Ann.

Go wherever moves you, even if it is off the beaten path. E-bikes give you the freedom to discover more because they won’t tire you out the way that traditional bicycles can. You will only be restricted by the 8 hour time limit on the bike rental, but that gives you plenty of time to explore!

Rentals can be booked here, and they start at $61.54 a person. The bike can be dropped off at any hotel or home in the area!

Aerial view of the beaches along the Gloucester Mass shoreline

Go to some of the best beaches on the North Shore

New England’s coastline is home to many beautiful beaches. In Gloucester, you’ll find that are some particularly stunning areas to enjoy the white sand and salty sea air.

Wingaersheek Beach is one of the best spots for a seaside stroll, though technically this beach is on the shore of the Annisquam River (which feeds into Ipswich Bay). There are tons of tidal pools to investigate, as well as sandbars, dunes, and rocks aplenty. Plus, there are lifeguards from 9-5, except during the off-season. There are also showers and bathrooms available.

If you’re in the area, you also won’t want to miss Good Harbor Beach. This is one of the region’s most popular destinations for surf and sand, for good reason. It’s incredibly scenic with stunning views of the sea, as well as the twin lighthouses that can be found on Thacher Island. There are also lifeguards in the summer here, as well as bathrooms and showers year-round.

Just a short way over in Rockport, you can find another incredible beach. Long Beach doesn’t have the same amenities as the Gloucester beaches, but this quant beach-house-lined stretch of sea and sand makes up for it with stunning views of the twin lights on Thacher Island.

Buy fresh seafood from a fishmonger

If you love lobster, crab, or fish, you might just mistake Gloucester for heaven. That’s because this little Massachusetts town is an active fishing port. In fact, Gloucester is the oldest fishing port in the country.

This means that you won’t be able to find seafood fresher anywhere else! So it would be a crime to visit Cape Ann and not taste the local fare, especially since eating out is one of the best parts of traveling.

A few local favorite fish mongers include Turner’s Seafood Market, The Fresh Lobster Company, and Connolly Seafood. However, you’re sure to find plenty of other options if you just explore!

Shop at independent bookstores

When you’re on vacation, especially at the beach, it can be nice to dig into a good book. There’s nothing more relaxing than setting up a towel or chair on the sand and getting lost in a story. So if you’re in the market for a good book while you’re in Gloucester, why not shop small and support a local bookshop?

Even if you’re not a reader, you can still appreciate that Dogtown Books is one of the coolest stores in town. This shop specializes in “used and unusual” books and has been providing Gloucester with books since 1997. They also frequently host book clubs, open-mic nights, author events, and readings, so it’s worthing checking their schedule for the dates that you’ll be around!

Another great option is The Bookstore of Gloucester. This historic shop has been operating since 1974, and offers an incredible and curated selection of stories. If you’re looking for a great read, they have you covered.

Wander the Hammond Castle Museum

If you’re looking for something truly unique, the Hammond Castle Museum offers a really special experience. After all, how many European Castles can you find in the American Northeast?

The museum is a great place to learn about the life and creations of the inventor, John Hays Hammond Jr. He was a bright man who is most known for his work on radio control and there are numerous exhibits that cover his contributions to technology.

However, the real draw of this museum is the stunning architecture that can transport you in time. In the 20s, Hammon commissioned a residence to be built on a bluff that looks out onto the Atlantic Ocean. His goal was to recreate a Medieval Castle for himself.

The building’s stunning architecture features design components from every century from the 1400s on, and it’s truly a sight to behold. Hammond was inspired by his love of history, and this also drove him to amass a huge collection of artifacts from the Renaissance, Middle Ages, and earlier periods as well. Many of these are on display at the Hammond Castle Museum, so it can be a beautiful place to learn about art and times that have passed, as well.

Tickets can be purchased on the museum website. They are $20 for those 12+, $15 for senior citizens, and $10 for children between 5-12. Kids under 5 can get in for free!

Rent a boat

If you’re looking to explore Cape Ann, don’t feel limited to land! There are tons of opportunities to get out on the water and enjoy the ocean. And if you’re over 21 and have a driver’s license, renting a boat can be one of the most amazing ways to experience the sea.

Gloucester Boat Rental offers a variety of different boats that can be taken out by groups with up to 8 passengers. The boats can be rented for a full or a half day, and you’ll be able to assume the Captain’s role and tour the area however you would like to.

Prices vary depending on the boat you select, but you can learn more about the options here. For a full-day, an inflatable boat can be rented for as little as $500!

Go fishing

If you’re in New England for the seafood, what better way to enjoy fresh fish than to catch it yourself? Plus, fishing isn’t just rewarding for your stomach, it’s a really fun and relaxing way to pass the time and enjoy the water.

Yankee Fleet Deep Sea Fishing has been offering fishing excursions since 1944, so there is no company more seasoned and qualified to take you out on the sea. Plus since there is a captain and full crew on board, you won’t need to worry about anything besides your catch.

There are many different packages available for different trip lengths. However, half days start at $50 a person for 4.5 hours, and a full 9 hour trip is $74. There are also longer excursions available, including overnights.

Sail on the Schooner Thomas E. Lannon

Since Gloucester is America’s oldest fishing port, it’s a town steeped in history. It can be fascinating to take a step back in time and learn about what life was like for previous generations. One particularly fun way to explore the local history is to charter the Schooner Thomas E. Lannon.

Taking a ride on this sailboat will allow you to simulate the experience of fishermen in the early 1900s. Plus, it’s just a beautiful way to get out on the water. The Thomas E. Lannon can hold up to 49 passengers. This vessel also comes equipped with snacks and a bar so that you can have a perfect time aboard.

Public sails last around 2 hours and start at $48 for adults. There are also sunset cruises and private charters available too. You can find more info here.

A lighthouse in the distance in Gloucester, MA with rocks in the foreground

Visit the Eastern Point Lighthouse

The lighthouses that decorate the New England coastline are a sight to behold. These charming structures draw in tons of tourists, as they are found in scenic surroundings and offer a fascinating window into the past.

The Eastern Point Lighthouse in Gloucester is one of the top attractions in the area, so if you’re in Cape Ann, it’s worth checking it out. This lighthouse was first built in 1832 and makes for a beautiful photography subject.

Unfortunately, as the lighthouse is now operated by the United States Coast Guard, it is not currently open to the public. However, it is still worth exploring the area so you can get a glimpse of it, even if you can’t go inside.

Indulge your sweet tooth at Holy Cow Ice Cream

If you get a hankering for something sweet while you’re exploring Gloucester, you’ll definitely want to stop into the Holy Cow Ice Cream Cafe. It’s a fun little joint with a great atmosphere and even better desserts.

Holy Cow offers really high-quality ice cream that is entirely homemade. On top of that, they have an eclectic menu that includes some really fun and exciting gourmet flavors. Cinnamon Churro Dough, Pineapple Upside Down Cake, and Cold Brew Oreo are just a few of the delicious flavors that you may not find elsewhere. If you want something really special, their ice cream sandwiches can’t be beaten either.

Holy Cow is also great if you are vegan, lactose-intolerant, or traveling with someone with one of these dietary restrictions. They have a separate menu that is entirely vegan and dairy-free, so everyone can enjoy a cone!

See a performance at the Gloucester Stage Company

For some culture and a chance to support the local arts, look no further than the Gloucester Stage Company. This professional theater company is also a non-profit that works to enrich the local community with engaging performances throughout the year.

Past performances have included classic shows like Spring Awakening and Shakespeare’s Hamlet. However, the Gloucester Stage Company makes a point to put on productions that are lesser-known as well. Furthermore, they are committed to diversity in their programming and take representation to heart when selecting a piece to perform and when they are casting.

Tickets start at $54 for adults, but package deals are available if you want to attend every play in a season.

Sunset cruise dinner (Beauport Cruiselines)

When you’re in a town known for its fishing, what could be more fitting than to indulge in some seafood on the water? A dinner cruise is a wonderful way to experience the sea. You’ll be able to really feel luxurious as you drink and dine on lobster while aboard a beautiful ship.

Beauport Cruiselines offers numerous fun trips, but the Sunset Dinner Cruise might be the most exciting. You’ll enjoy a New England Lobster Bake Dinner and be able to appreciate a full bar, live entertainment, and of course, the ocean.

Tickets start at $69 per person. There are also lunch cruises and special events that are available as well.

Stop by the “Cut Bridge”

Blynman Bridge is referred to almost exclusively as the “Cut Bridge” by the locals of Cape Ann. This little drawbridge is one of the most active on America’s eastern shore. In fact, some days, it is raised as many as 60 times.

It goes across the Blynman Canal, which is the connector between Gloucester Harbor and the Annisquam River. The Canal dates back to 1643, but the bridge was not constructed until 1907. There’s a lot of local history wrapped up in this little waterway, which is part of why a visit to the Cut Bridge can be so nice.

The Cut Bridge is also just a lovely sight for bridge enthusiasts or anyone looking to take in some of the quaint charm of New England. If you’re in the area, it’s definitely worth just taking a stroll by and snapping some photos of the bridge.

Go on a food tour

There are a lot of great things about traveling. There are new sights, cultures, history, and people to explore, which can be really exciting. However, without a doubt, one of the most enticing parts of going somewhere new is trying the local food.

New England is home to some phenomenal seafood, as well as many other great cuisines. In fact, there’s such an abundance of good food that you might not know where to begin. That’s the beauty of a food tour: a seasoned guide will take you to the best spots and let you sample a little bit of everything.

The Gloucester Food Tour from Cape Ann Foodie Tours will lead you to five to six different spots. You’ll be able to taste a classic chowder, some authentic cannolis, and many other delicious dishes. The tour is $59 per person, which covers all of the food. However, this does not include gratuity.

Go paddleboarding

Want an active way to enjoy your vacation and get out on the water? Paddleboarding can be just what you’re looking for. Stand-up paddleboarding can be a great workout, and it’s also a lot of fun. It’s the perfect activity for anyone looking for a little adventure while they’re in Gloucester!

Cape Ann SUP + Surf offers tons of different paddleboarding options that can accommodate all skill levels. If you’ve never tried it before, there are group or private lessons that you can sign up for. If you know the basics but would prefer a guided experience, you can also go on a paddleboard tour. There are also SUP Yoga classes and paddleboard rentals available if you’re ready for something more advanced.

Group lessons are $45 per person, and tours are $65 for each person. If you’re interested in renting a board and going off on your own, it’s $60 for 4 hours or $80 for a full day.

Attend a festival or special event

Depending on when you’re in town, there may be some exciting events happening. This is especially true in the summer when there is almost always something going on in Gloucester. Taking advantage of the local happenings can be a great way to have a unique experience and make some really special memories.

If your dates line up, the Riverfest Seaside Music Festival is one event that you won’t want to miss. There is always a great roster of live music to be found at this festival, plus lots of food trucks, entertainment for the kids, and plenty of booze for the adults.

If you’re able to, you should also check out St. Peter’s Fiesta. This is a five-day festival that happens every year in Gloucester to celebrate St. Peter, who is known to be the patron saint of fishermen. It’s one of the most exciting events in the Cape Ann area, and it brings in visitors from all over. There will be boat races, a carnival, a greasy pole contest, and much more!

Fisherman's Memorial Statue in Gloucester Mass
via Ark Neyman on Shutterstock

Go to the Fisherman’s Memorial Monument & Fisherman’s Wives Memorial

As you may have gathered, Gloucester is a city that is pretty big on fishing. It’s America’s oldest fishing port, and the local economy still actively relies on this industry.

However, fishing can be a lonely and hard profession since much of the fisherman’s life is spent on the water, away from land, creature comforts, and his family. It can also be a dangerous career path, especially in the deep sea.

The Fisherman’s Memorial Monument seeks to honor and thank all of the fishermen who have sacrificed for their community. This statue commemorates the significance of this industry to Gloucester, and acknowledges the men who have sustained it.

But the burdens of the fishing industry don’t rest on the fishermen alone. They are also leaving behind wives who have to carry on in their absence. This can be a difficult burden to bear, especially when there are children. That’s why the Fisherman’s Wives Memorial honors the women behind the fishermen.

Spend an afternoon at the Cape Ann Museum

The Cape Ann Museum showcases the art and history of the region in a historic building that has become a shining beacon for the community. 

The museum was established in 1875 as the Cape Ann Scientific and Literary Association, but it has since evolved into a thriving cultural hub. The main site is located in downtown Gloucester. It has an auditorium, Library & Archives, children’s activity center, two sculpture gardens, a captain’s home from the 19th century, and various galleries housing both permanent and temporary exhibits. The Cape Ann Museum Green was inaugurated in 2020 as the new location of the Museum. Three historic buildings, open green space, and a brand new, state-of-the-art Collections Center can all be found at 13 Poplar Street in Gloucester, where CAM Green is housed. The Collections Center also has more space for displaying and storing CAM’s collections.

Get Spooky in Dogtown Common

Part of the Essex National Heritage Area, Dogtown Common is a legit ghost town. Its history is both strange and exciting. This area has rumors of suspicious drifters, wolves, witches, werewolves, curses, and scary dolls. 

Settlers first arrived in the region in 1693, drawn there by the relative safety afforded by the area’s interior location from both pirates and the native peoples, who were naturally displeased by the influx of strangers. Approximately one hundred households called Dogtown home during its heyday (1750-1800).

Dogtown, formerly known as the Common Settlement, received its name from the free-roaming pack of strays often seen in the area. Many women who had lost husbands at sea or in battle kept dogs for self-defense and company. These animals grew wild when their owners died and now roam the adjacent grasslands.

During the Great Depression, Roger Babson, founder of Babson College, hired unemployed stonecutters in Dogtown to carve uplifting messages on boulders and stones left behind by the glaciers melting. 36 of these mysterious and oftentimes unnerving writings are strewn throughout the landscape.

Dogtown in Massachusetts is now a rocky 3,000-acre park where tourists may explore the trails and tangled trees that once covered the town and discover the village’s abandoned cellar holes. However, many visitors have complained that the region is difficult to navigate due to its hazardous terrain and crumbling ancient farmstead foundations. The curious traveler hankering for a ghost town experience must visit Dogtown – with caution.

Stage Fort Park 

When the first immigrants arrived in Gloucester in 1623, they established fishing stages in this area. Half Moon and Cressy beaches may be found at Stage Fort Park, along with a sand volleyball court, a brand new playground, a baseball field, a basketball court, and tennis courts. There are public facilities, a visitor center with maps and information, a privately operated restaurant serving food, and many picnic tables and grilling sites (bring your own grill). There are various festivals, farmer’s markets, fireworks displays, concerts, and storytimes for kids throughout the summer. 

Ravenswood Park 

The environmentalist ideals of the park’s creator are reflected in Ravenswood Park’s 600 acres of calm space for reflection. Businessman and philanthropist Samuel Sawyer of the nineteenth century bought more than twenty-six parcels of land near his home on Freshwater Cove, including woods, pastures, and a swamp. Upon his death, Sawyer bequeathed this land to be developed into a park, which would be called Ravenswood, after the castle in Sir Walter Scott’s The Bride of Lammermoor. Snow-covered hemlocks, the fresh scent of spring, and relief from the sweltering heat of summer all await you here.

Rafe’s Chasm

The Trustees of the Reservation sold Rafe’s Chasm Park, a 10-acre space, to the City of Gloucester for a dollar in 1959. 

Views of Norman’s Woe rock to the northeast and Kettle Island to the southwest may be enjoyed from this beachfront park that stretches from Hesperus Avenue to the rock.

About fifty yards away from Rafe’s Chasm Park is private property where the chasm itself may be found. Please respect any signs that read “Private Property.”

This massive rock fissure, once known as Rafe’s Crack, was renamed Rafe’s Chasm on maps in the 1850s.

Legend has it that a formerly enslaved man called Ralph resided in the area around the Chasm and constructed many of the rock walls that can still be seen today along Hesperus Avenue, thus the name.

After the end of the Civil War, the chasm was discovered and quickly became a major tourist attraction.

Visit Beauport, the Sleeper-McCann House

Sleeper-McCann House in Beauport is a National Historic Landmark because it was the vacation home of Henry Davis Sleeper, one of the first professional interior designers in the United States. Beauport, which Sleeper built on a rock outcrop overlooking Gloucester Harbor, served as his haven, stage for social gatherings, and professional display.

The McCanns bought Beauport after Sleeper’s death and substantially preserved it. Travel to Beauport to explore every nook and cranny of Sleeper’s lifelong collection of oddities, colorful glass, folk art, ceramics, and silhouettes. There are forty unique rooms, each with its own theme, color scheme, decorative accent, or literary or historical character. In this hotel, there is no room that is like any other, and all of them are absolutely stunning. Meet Sleeper, a gay man who lived in the early 20th century, his housekeeper Mary Wonson, his interesting neighbors, and the house’s numerous eccentric visitors.

Visit the Cape Pond Ice Company

In 1848, blacksmith Nathaniel R. Webster founded Cape Pond Ice Company, then known as Gloucester Co., in response to the growing need for a consistent supply of ice by the fresh fish business. Fish, especially halibut and cod, were preserved in salt and brine prior to then.

Webster’s first ice house was constructed by damming a nearby creek.

Within four years, Webster constructed ice houses on Upper and Lower Day’s Ponds, near Foster’s Serv Station, and on Cape Pond in Rockport; the latter is now the company’s primary location.

In 1858, Webster’s son succeeded to the family’s ice monopoly in Cape Ann. 

These days, The business is available for commercial appointments at any time of day or night, all year round. In addition to filling tractor trailers and trucks with block ice or blown crushed ice, Cape Pond Ice can pump at a rate of one ton per minute on up to three fishing boats simultaneously. Pallets of bagged ice ranging in weight from 30 to 40 pounds are transported all throughout Cape Ann and New England.

The business caters to a wide variety of customers, including commercial fishing boats and processors, broccoli and poultry growers, redi-mix concrete builders, and customers who want unique ice sculptures. 

A viewing window in the office looks out on the 150-ton-per-day ice block manufacturing area. Tours of the facility are no longer available, but visitors may hear a free history talk in the gift shop, watch historic video footage, or take a peek at the wharf. 

Explore downtown Gloucester

Gloucester, Massachusetts, is the oldest continuously operating seaport in the United States and is known for its nautical heritage, delicious seafood, bustling waterfront, and stunning beaches. Experience the finest of New England’s coastal natural splendor while on land and marine activities. Downtown Gloucester has award-winning restaurants, chic stores, fun events, and a lively arts and culture scene.

Small Business Saturday, November 26, marked the beginning of the third annual Winter Lights on Cape Ann celebration, which continues until New Year’s Day, January 1.

Businesses in Essex, Gloucester, Ipswich, Manchester-by-the-Sea, and Rockport are joining up this year to decorate their establishments with more than one hundred holiday lights displays. Lights and elaborate window decorations are being set up in stores as a way for owners to get into the Christmas mood.

Rocky Neck Art Colony & Cultural Center

One of the earliest art colonies in the US may be found at Rocky Neck. Rocky Neck, a small peninsula in Gloucester’s working harbor, is well-known for its scenic beauty, its distinctive light, its rich cultural past, and its lively, supportive community.

Some of the most influential figures in American art history, such as Winslow Homer, Edward Hopper, Frank Duveneck, and Childe Hassam, were among the Plein air painters who called Rocky Neck home in the late 19th and early 20th centuries.

Many other modernists, such as Stuart Davis, Milton Avery, Adolph Gottlieb, Nell Blaine, and Mark Rothko, were also drawn to Cape Ann by its picturesque scenery and active waterfront.

Rocky Neck galleries host the works of dozens of local artists every summer, from painters and potters to textile designers, photographers, and even jewelry makers.

There is a wide selection of dining options to suit every palate, and on the weekends, many establishments provide live music to enhance the atmosphere further.

The Rocky Neck Art Colony, located in Gloucester’s Rocky Neck Cultural District, is a terrific area to take a walk on a sunny summer day, stop by on the way to or from the beach, or have a delicious dinner.

Visit Rockport 

A nearby town to Gloucester, Rockport is striking in its seaside beauty. Rockport played the role of a small Alaska village in the 2009 film The Proposal, starring Sandra Bullock, Ryan Reynolds, and Betty White.

I recommend watching the movie the night before you head to Rockport! It’s fun pointing out all the locations, from Motif No. 1 to the Fudgery and noticing the CGI mountains in the background.

There are a few things everyone visiting Rockport must do — explore Bearskin Neck, enjoy a lobster roll, and explore Halibut Point State Park.

You can grab a lobster roll at several locations, but I recommend Roy Moore Lobster Company and The Lobster Pool.

Roy Moore is in Bearskin Neck, so you can grab a lobster roll and take a short walk on the long beach there, hitting Motif No. 1 and checking out the other sites.

There are also breweries, beaches, art galleries, and much more. Check out my post all about Rockport here.

Visit Essex 

Essex is next door to Gloucester and is great for antiquing and seafood. It is known as the “Restaurant Capital of New England” due to the high concentration of eateries per resident.

Many of its traditional and innovative dining establishments are situated on the riverbanks of the Essex, with picturesque views of the estuary and Great Marsh. 

Essex is a great year-round destination for foodies because of its abundance of restaurants serving anything from freshly caught seafood to classic New England specialties with a creative twist. 

Sit back with a craft beer or beverage and watch the boats go by while you soak up some sun on an outdoor deck. When the weather outside is chilly, you may warm yourself by dining next to a fire.

Gloucester is jam-packed with rich cultural and historical sites, delicious food, beautiful art, and stunning scenery. When will you visit?

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