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32 Fun Things To Do In Gloucester, Massachusetts

So, the warmer weather and longer days have you thinking about a coastal escape. We’re with you 100%. Whenever St. Patrick’s Day starts rolling around we start getting restless and start thinking of beaches, boating and consuming copious amounts of crustaceans.

If you’re thinking of heading up to Cape Ann for a little rest and relaxation this Summer or Winter/Fall for that matter, then this article is for you. Here are 32 fun things to do in Gloucester, Massachusetts.


1. Good Harbor Beach

So, we think a logical place to start a discussion about things to do in Gloucester, MA is to talk about its incredible beaches. Gloucester is home to some world class beaches that are truly some of the best in New England. One of our favorite Gloucester beaches is Good Harbor Beach.

Good Harbor Beach Things To Do IN Gloucester MA

With beautiful soft white sand, a large area to spread out, incredible views of the Thacher Island lighthouse, and the ability to walk out to Salt Island during low tide, Good Harbor is a fantastic spot to spend a Summer day.

In the off-season you can still enjoy the beach and even bring your dog out for a run to burn off some of that extra energy. To learn more about Good Harbor you can read our Definitive Guide To Good Harbor Beach


2. Take an Historic Sail

Take a step back in time and set sail out of Gloucester Harbor aboard the 65-foot Schooner Lannon. Get a feel for what life was like aboard this authentic fishing schooner. You can even book a private charter or have a wedding aboard the ship!

Schooner Lannon Gloucester

The striking schooner was built in 1997 in Essex, MA. Framed with local white oak and black locust, the schooner has a length on deck of 64.5 ft and overall length of 90 ft.

The Schooner Lannon offers a variety of food options as well as beer, wine and other drinks to enjoy during the sail. It’s a fantastic way to get a different look at Gloucester harbor.


3. Get Some Fresh Seafood From A Fishmonger

Gloucester is a working fishing port and home to some of the freshest seafood that you can buy. Whether you are looking for some fresh lobster, cod, tuna, or stuffed quahogs Gloucester has you covered! 

Fishmonger Gloucester

A few of our favorite local shops include:

Connolly Seafood: http://www.steveconnollyseafood.com/
Captain Joe & Sons Lobster: http://www.wholesalelobster.com/
Turners Seafood: https://www.turners-seafood.com/gloucester-market/


4. The Perfect Stop, For The Record

We miss record shops. The process of finding the perfect album or discovering a hidden gem and the tangible community experience. And, if you think we are the same people that still like actual books better than e-books, consider us guilty as charged.

Mystery Train Records Gloucester MA

If you’re looking to take a step back in time and find the perfect record or that CD that you used to love you have to take a trip over to Mystery Train Records.

Located right on Main Street in Gloucester, Mystery Train has a great selection of rare & collectible vinyl from just about any genre you can imagine. Heck, they even have eight track tapes!

If you’re up in Gloucester, it’s definitely worth a stop!


5. Shop at Independent Bookstores

Speaking of actual books, Gloucester has some incredible independent bookstores where you can peruse the stacks and find some incredible beach reading. A couple of stores that we love are Dogtown Books and The Bookstore of Gloucester

Things to Do IN Gloucester MA

Dogtown Books offers a wide selection of preowned books, certified pre-owned books, and just general used books to choose from. They topics range from culinary adventures to space exploration and the owners are very friendly and welcoming.

The Bookstore of Gloucester on the other hand has been serving Cape Ann readers for over 45 years and offers the perfect local alternative to Amazon. It’s a great spot to pick up the latest releases and browse the curated collection.

If you are interested in Independent Bookstores take a closer look at our article on 5 Great Independent Bookstores on Cape Ann.


6. Step Back Into Medieval Times

If you are a fan of history and architecture, you have to make a point to stop at Gloucester’s Hammond Castle. Constructed by the eccentric inventor John Hays Hammond in the 1920’s, Hammond Castle serves as a beautiful showcase for Hammond’s impressive collection of Roman, Medieval, and Renaissance artifacts.

Hammond Castle

John Hays Hammond was a legendary inventor, holder of over 400 patents and is known as “The Father of Remote Control.” Visitors can tour the courtyard, great halls, secret passageways and war room and marvel at the beauty of the castle grounds.

In October, Hammond Castle even gets in the Halloween spirit with special haunted tours. If you fall in love with the castle you can even decide to host your wedding on site! It’s such a cool venue that it made our list of the Top 5 Gloucester MA Wedding Venues.


7. Rent Some Toys

We all know the common sayings about boats: “a hole in the water you throw money in” and “break out another thousand.” Of course there is some truth in the sayings, but enjoying Cape Ann on the water gives you a whole new appreciation for this incredible landscape.

Fishing In Gloucester MA

Instead of buying a boat, paying for a slip, paying for fuel, registration, maintenance etc. why not just rent a boat? Well, at Gloucester Boat Rental you can do just that! They have a nice selection of boats from Key West, Striper, Sea Pro and Grady White that you can rent for 4 hour and 8 hour increments.

So grab a couple friends, a couple fishing poles, and something to sip on and hit the open ocean for the day.


8. If You Get Confused Listen To The Music Play

Covid has had us all itching to get back out and see some live music. A great local spot in Gloucester to catch music is Minglewood Harborside. Owned by the Serenitee Restaurant Group, they have a Jam Session every Monday night as well as other musical acts throughout the week.

Minglewood Gloucester

Recently remodeled, Minglewood offers a large bar area adorned with some hearty nods to Jerry and the Boys. The menu at Minglewood truly has something for everyone from burgers and pizza to sushi and fresh seafood dishes.

So knock back a couple more shots of whiskey and head on down to Minglewood.


9. Visit Eastern Point Lighthouse

Cape Ann has no shortage of lighthouses and one of the best around has to be the Eastern Point lighthouse. This iconic lighthouse was originally built back in 1832 and reconstructed a couple of times.

Eastern Point Lighthouse

The current 36 foot tower was built in 1890 and has an attached 2 story keepers quarters. Eastern Point You will see images of Eastern Point in publications about Gloucester and the lighthouse was even home to Winslow Homer back in 1880.

You can drive out to the light, park and take the half mile walk out on the dog bar breakwater to the Dog Bar Lighthouse. It’s a beautiful area and a great spot for a sunset or sunrise. If you want to see some incredible footage of the lighthouse you have to check out this Kenny Chesney video that was shot in Gloucester


10. Get Some Tasty Ice Cream

We love Ben & Jerry’s. They were the hearty pioneers that took it upon themselves to open an ice cream shop in Burlington, VT, of all places. But they had a vision and they paved the way for ice cream as we know it today.

Holy Cow Ice Cream

Following in their footsteps is Holy Cow Café in Gloucester, MA. We think Holy Cow can best be described as Ben & Jerry’s meets Christina Tosi’s Milk Bar. One bite of this ice cream will have you invoking their name.

With cereal infused flavors like Gold Rush (Frosted Flakes steeped ice cream loaded with Golden Oreos!) and Cereal Milk (Fruity Pebble steeped ice cream mixed with colorful cereal marshmallows! Colored with all natural Blue Spirulina!) you are sure to be transported back to your 11 year old self.

Holy Cow also does exclusive flavor collaborations with local businesses such as the Taste The Rainbow collaboration with Gloucester’s Cafe Sicilia (pictured above). If you have a sweet tooth then you should definitely put Holy Cow Ice Cream on your list of things to do in Gloucester, MA. 


11. Head To The Theatre

The Gloucester Stage Company, founded in 1979, is an award-winning company that is a vital part of the fabric of Gloucester.

Since 1987, the Company has called East Gloucester home. Their performance center is housed in a former Gorton’s Fish Company Warehouse that Gorton’s kindly donated to the Company. It doesn’t get much more Gloucester than that!

The intimate but comfortable venue includes a refreshment bar and foyer and is a fantastic spot to catch a show. We’d recommend grabbing a bite at nearby Duckworth’s Bistrot before the performance.


12. A Whale Of A Time

One of the most popular activities on Cape Ann is whale watching and we would highly recommend it. Sign up with Seven Seas or Cape Ann Whale Watch and head out to marvel at these mammoth mammals.

Whale Watching in Gloucester MA

The most common whales that you will find off the coast of Gloucester include the Humpback, Minke and Finback but you may also get a chance to see dolphins, sharks, and sperm whales.

On the three hour tour you will likely see the whales dive, breach, lay on their back and slap their fins and if you’re lucky you may even witness a bubble net! Learn more here: Gloucester Whale Watch Discount


13. Relax, They’ve Got Your Back

If you’re looking to relax and unwind, there’s no better medicine than a good massage. Gretchen and skillful team at Saltwater Massage in Gloucester are second to none and you can rest assured that you will come out of Saltwater feeling calmer and happier than when you arrived.

Saltwater Massage

Whether you are looking for CBD Massage Therapy, Therapeutic and Deep Tissue Massage, Prenatal Massage, or you’re into hot stones and cupping, they have you covered.


14. When In Rome…Light One Up

So recreational marijuana is now fully legal in Massachusetts. You can now walk right into a dispensary and acquire the devil’s lettuce and a variety of other products that can heighten THC levels in your body.

Happy Valley Gloucester MA

Whether you prefer to smoke, vape, munch on edibles or drink an elixir, Happy Valley Dispensary in Gloucester has your cannabis needs covered.

Whether you are a regular user or are just looking for a flashback to the glory days, a stop at Happy Valley is sure to make your journey to Cape Ann a little more interesting.


15. Take A Sunset Dinner Cruise

Set sail aboard the Beauport and take a sunset cruise while enjoying a delicious seafood feast of lobster, corn, and clams. Enjoy the views of Gloucester Harbor including the downtown, Eastern Point, Rocky Neck, Stage Fort Park and Hammond Castle.

The boat comes equipped with a full bar so you can enjoy your beverage of choice. The cruise lasts a couple of hours and it’s a great way to cap off a beautiful day up in Gloucester, Massachusetts.
In addition to dinner cruises, Beauport Cruiselines also offers lunch cruises, live jazz Sunday brunches and you can even book a deck or the entire boat for your wedding.


16. Acai Bowling 

Food trends come and go but acai bowls are forever. The acai bowl is essentially a healthy smoothie with tasty toppings that is the perfect way to start your day.
Acai berries (annoying guy says that technically they are drupes) are a superfood that come from the rainforest that are loaded with antioxidants, boost brain function and lower cholesterol levels.

In Gloucester, you can get your acai on at Castaways Vintage Café

Castaways is an adorable café that offers acai, some delicious coffee beverages as well as vintage clothing. The vibe at Castaways is an island vibe that is mix between tiki hut and surf shop. When that Acai craving hits, Castaways is your destination. 


17. Revel In The Cut Bridge Carnage

The Blynman Bridge, also known as the “cut bridge” is a bridge that was built back in 1907 to honor Richard Blynman, the first minister and a prominent citizen of Gloucester. Blynman’s efforts were pivotal in digging the canal connecting the Annisquam with Gloucester Harbor.

Cut Bridge Gloucester

Blynam’s cut through the isthmus took place in 1643. The bridge is now a popular spot for locals and tourists to loiter and watch the boats head in and out.

Some of the boats from Wicked Tuna dock at nearby Cape Ann Marina so you can sometimes catch celebrity boats like FV Tuna.

To get a taste of the carnage you can watch the Captains navigating the tight canal on the Cut Bridge Craziness Instagram page. It’s a fun take for a few laugh and some questionable navigation decisions.


18. Get Your Vitamin Sea at Wingaersheek

If you are itching for some beach time and some of that thick salt air it’s always a great plan to head over to Wingaersheek Beach. One of our favorite Gloucester beaches, Wingaersheek offers a beautiful beach that runs along Annisquam River and Ipswich Bay.

Wingaersheek Beach

Known for its long sand bar at low tide, Wingaersheek is a great spot to spend a Summer day in Gloucester and that’s why it had to be on our list for the best things to do in Gloucester, MA. If you want to learn more about Wingaersheek, check out this Definitive Guide to Wingaersheek Beach.


19. Hop On A Foodie Tour

What better way to explore the coastal cuisine of Gloucester, Massachusetts than on a foodie tour! Try a little bit of everything and learn about some of Gloucester’s hidden gems on the Cape Ann Foodie Tour.

Cape Ann Foodie Tour

From thick and tasty claim chowder to homemade olive oil and delicious Italian sandwiches, Cape Ann Foodie tour will expose you to the culinary delights of the area.

Learn more about their schedule and some of the stops here – Cape Ann Foodie Tours


20. That’s What’s SUP

Want to get out on the water and try something a little different? How about stand up paddle? Cape Ann SUP has you covered. With locations at Pavillion Beach in Gloucester, Long Beach and on the Essex River.

Cape Ann SUP

Cape Ann SUP offers stand up paddle tours, surfboard rentals, and yoga classes.

The staff are all super friendly and knowledgeable and will provide you the necessary instruction so that you can get out there and have some fun on the water. We’re not saying you’ll become Kelly Slater by the end of the day, but we promise that you will have some fun and make some memories.


21. Scuttle Across The Rocks at Rafe’s

If you are looking for a short hike that takes little effort but offers a big reward, then Rafe’s Chasm is the hike for you! Located at 138 Hesperus Ave in the Magnolia neighborhood of Gloucester, Rafe’s Chasm provides a great cliff top view after a short flat hike through the woods.

Rafe's Chasm

Rafe’s Chasm has an interesting history death and shipwrecks and is a popular spot for adventurous divers.

Click here to learn more about Rafe’s Chasm and it’s history.


22. Fishing For A Good Time

Embrace your inner angler with a trip out into the historic Atlantic on a deep-sea fishing charter. Set out on the same waters as Captain’s Courageous, and the Perfect Storm and try your hand at hauling in some stripers, cod, halibut, and haddock.

You can choose from a half day (4.5 hours), full day (9 hours), or a fishing marathon (12 hours). You will head out to the deeper waters and fish anywhere between 100 and 300 feet.

The Yankee Fleet offers 3 fantastic vessels to choose from: The Yankee Freedom, a 100 foot vessel that can accommodate 135 passengers, The Yankee Clipper, a 75 foot vessel that can accommodate 113 people and The Yankee Patriot II.


23. A Perfect Storm

After you get back from fishing, knock a few back at the Crow’s Nest. Featured in the blockbuster hit, The Perfect Storm, the Crow’s Nest is the perfect embodiment of Gloucester’s working waterfront.

Gloucester MA Fishermen

The Crow’s Nest has offered Gloucester fisherman, locals and tourists drinks and accommodations for over 40 years. The walls are full of memorabilia from the movie and pictures of the actual crew from the Andrea Gail. It’s a local dive, but the folks are friendly and the drinks prices are fair.

You can check out some pictures from their gallery here: Crow’s Nest Gallery 


24. Rocky Neck Art Colony

One of the oldest continuously operating art colonies in the United States, Rocky Neck is a great place for a summer visit.
Over the years, the unique landscape, beautiful light, and rich culture has drawn many artists to the shores of Gloucester. Some famous plein air artists include Winslow Homer, Edward Hopper, and Childe Hassam. The area was also frequented by writers Rudyard Kipling and Louisa May Alcott.

Rocky Neck Art Colony

The art colony is still a vibrant community with a large membership, many of which still have studios on Rocky Neck.  It’s a beautiful place for a stroll and there are some great restaurants like The Studio and Duckworth’s Bistrot nearby should you need some sustenance.


25. Stay At A Local Inn

One of the great things about traveling to Cape Ann is that there really are not any chain hotels in the area. All the lodging properties are privately owned and offer a unique staying experience.

One popular lodging option for travelers to Gloucester is the Blue Shutters Inn. Located right off of the shores of Good Harbor Beach, Blue Shutters provides guests a comfortable and convenient location for their coastal escape.

Blue Shutters Inn

Another option for Gloucester travelers is the stay at one of the historic inns in Rockport, Massachusetts. Rockport offers a great variety of inns including the stylish and charming, Addison Choate located right in the heart of the coastal village.

Addison Choate Rockport MA Inn

Regardless of where you choose to hang your hat, you are sure to be treated to hospitality that is second to none.


26. Outdoor Concert In The Park

Every year in August, Stage Fort Park in Gloucester turns into a mini-woodstock when the Riverfest Seaside Music Festival comes to town. The festival was cancelled in 2020 due to Covid, but in 2019 the festival featured Tall Heights, Mt Joy, Noah Kahan, and was headlined by good old Guster.

The best part is that the festival is open to the public, free of charge!

In addition to music, the festival also includes food trucks, a beer garden and other tasty refreshments to keep you cool on a hot summer day. If you need to cool off you can also walk right over to beautiful Half Moon Beach and jump on in!


27. St Peters Fiesta

A long-time Gloucester tradition, St. Peter’s Fiesta is a 5-day festival that honors St. Peter, the patron saint of fishermen. The annual festival takes place in late June every year and features parades of statues, boat races, masses and prayer.

The highlight of the event; however, is the weekend long Greasy Pole Competition. The Greasy Pole Competition traces its roots back to Sicily in the 1800’s and was brought to Gloucester by Italian immigrant fishermen.

The spectacle involves a 40ft piling that is raised up 30ft above Gloucester harbor, greased up with bacon fat, Crisco and fish guts to create a slippery surface, and contestants must then run to the end of the piling and grab flag.

Winners will treated to adulation, complimentary libations and memorialization on the St Peter’s Fiesta Wikipedia Page. You can check out the list of past Greasy Pole Winners Here


28. Visit Fisherman’s Memorial Monument

It’s no secret that Gloucester has a rich seafaring tradition. Home to one of America’s oldest fishing ports comes with its ups and downs. Over the years, the town has lost many mariners to the Atlantic and in 1925 the iconic man at the wheel was constructed to honor their legacy.

The Man At The Wheel

The eight-foot-tall bronze statue rests upon a five-foot base and is inscribed “They That Go Down To the Sea In Ships, 1623 – 1923. It’s a powerful reminder of the power of the ocean, human mortality and the brevity of our time. Being tossed at sea in a modern vessel can be nerve-wracking, it’s frightening to imagine being miles off shore in an old schooner.

The Fisherman’s Memorial is located right off Stacy Boulevard and if you are visiting Gloucester, it’s an absolute must stop.


29. Interior Design Mecca

Perched on a ledge overlooking Gloucester Harbor is the home of one of America’s first interior designers, Henry Davis Sleeper. Beauport, the Sleeper-McCann House, was Sleeper’s summer retreat and the 40 room mansion houses Sleeper’s diverse collection of folk art, pottery, antiques and other artifacts.

Sleeper McCann House

A National Historic Landmark, each room is distinguished by a historical or literary figure and no two rooms are the same. The property even features a beautiful garden and a secret staircase. The Sleeper McCann House is open from late May to Mid-October and is definitely one of the best things to do in Gloucester.


30. A Day At The Museum

Another great stop for visitors to Cape Ann and Gloucester is the Cape Ann Museum. The museum is a celebration of art, history, and culture of Cape Ann.

The museum features a fine art collection which boasts some fantastic marine art from artists such as Fitz Henry Lane as well as other talented painters and sculptors who called Gloucester home.

Cape Ann Museum

It is also home to the Fresnel Lens from Rockport’s Thacher Island that dates back to 1861. Designed by French physicist August-Jean Fresnel, the lens cast a beam for 22 miles keeping Cape Ann mariners safe for many years.

In addition to its permanent exhibits, the Cape Ann museum has a fantastic rotation of special exhibits and other programs and events throughout the year.


31. Trek Through The Dogtown Wilderness 

Dogtown Common provides hikers with an incredible 3,600 acres of mysterious woods, large boulders and carved stone to explore. Originally settled back in 1693, settlers chose the location due to its rocky inland landscape that offered protection from pirates and combative natives. The settlement was abandoned back in the early 19th century and has not been inhabited since. 

Dogtown Common Rockport Gloucester

With some incredible trails, Dogtown offers a great opportunity for hiking, biking, running, cross country skiing and an outing with you furfriend. Along the paths you will find large boulders with sayings carved into them. These boulders were carved by unemployed Finnish quarrymen during the Great Depression who were commissioned by local entrepreneur Roger Babson.  There are 36 boulders that were carved with inspirational sayings such as “Never Try Never Win” and “When Work Stops Values Decay.” 

The name Dogtown is said to date back to the American Revolution and is derived from the dogs that the women kept while their husbands fought in the war. At one point it was estimated that there were anywhere from 60 to 80 homes in the area.  But after the war, the ports became safer, the fishing industry returned and so too did the settlers to the coastline. 

So if you’re in the mood for a journey off the beaten path, Dogtown is a great thing to do in Gloucester. Here is a link to a great Dogtown Guide


32. Get Your Omega 3 Fix 

While you are in one of America’s oldest fishing ports, you are probably going to consume some of that fresh bounty. Well, as you can imagine, there is no shortage of local restaurants serving up delicious seafood dishes.

If you are looking for a nice sit down meal with creative cuisine prepared by a talented chef, we would recommend Tonno, right on Main Street in Gloucester. If, one the other hand, you are thinking about getting a classic seafood platter with fried clams, haddock, shrimp and fries, then you should visit The Causeway. It’s a no-frills Gloucester institution that cranks out some really good eats.

Another excellent restaurant with a menu that runs the gambit from Sole Meuniere to Paella is Lobsta Land! Located right of 128 it has old school fish shack vibes, a nice marsh view, and some tasty cuisine. There are many other great places to stop as well, but these are a few that we love. 


32 Things To Do In Gloucester 

Well, we hope that you enjoyed our 32 Suggestions! This is really just scratching the surface of all of the things that there are to do and explore on Cape Ann. If you enjoyed this article you may also enjoy our article about 40 fun things to do in Rockport, Massachusetts! We hope that you enjoyed your trip up to Cape Ann, it’s truly a special place. 

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