Visiting Gloucester, Massachusetts isn’t what you might imagine for a beachside retreat. You won’t find luxury hotel chains here, nor will you find tropical cocktails on rooftop bars. Instead, you’ll find friendly, community-oriented people who love their home and are thrilled to be able to share it with you.

Gloucester is a strong fishing hub, so much so that many of the residents you meet likely are in the fishing industry or at least have family who have braved the rough sea. But in addition to being dedicated to maritime culture, you’ll find that Gloucester is filled with stunning art and architecture, delectable sweets and treats, and a multitude of ways for you to be at one with nature.

From beach days to evenings on the open sea, there are just so many fun things to do in Gloucester, MA. With so many options, you might not know where to begin. So we’ve compiled our list of the absolute best things to do in Gloucester for you. Stick to these fun and unique Gloucester bucket list recommendations, and there’s no doubt you’ll have a fantastic time exploring this friendly seaside haven!

The 15 Best Things to do in Gloucester, MA

1. Sail on the Schooner Lannon

The Schooner Thomas E. Lannon has been a part of Gloucester’s history since 1997, but its origins date back further than that. The boat is named after the owner, Tom Ellis’ maternal grandfather, who fished out of Gloucester from 1901 to 1943. The Schooner Lannon was designed to make you feel like you were sailing on a fishing schooner a hundred years ago.

These days, the boat offers two-hour sails and private charters from mid-May to mid-October, and these sails are some of the most unique things to do in Gloucester. When you climb aboard, you’ll be delighted by the views of Gloucester’s working harbor and the rocky coastline. 

You’ll take in lighthouses, beautiful beaches, and even historic castles. Unlike some other boat tours, this isn’t designed to be an educational journey. There’s no narrator on board. Instead, it’s just meant to be a peaceful cruise where you can be at one with the sea.

In addition to the standard cruises, there are also featured events throughout the year. Be prepared to boogie on the water with the Sunset Music Cruises. Or enjoy the atmosphere on a Moonlight or Stargazing Sail. If you’re visiting around the Fourth of July or during Labor Day weekend, you can join for a dessert cruise and take in the show during the Fireworks Sails. 

There’s also one very special sail that happens during the Gloucester Schooner Festival Race, which is held every Labor Day weekend. The Schooner Lannon always takes part in this race, and you’re invited on board. Join in for a day of adventure, fun, and one-of-a-kind views!

2. Spend a Day on Good Harbor Beach

As a seaside town, it’s no surprise that Gloucester boasts plenty of beautiful beaches. But one of the area’s top spots is Good Harbor Beach. Here you’ll find powdery white sand and astounding views, with rocky shores overlooking the water.

During low tide, you can walk out to Salt Island, a natural wonderland with no real trail system that requires a bit of a sense of adventure. You can climb to the rocky summit to take in the view of the mainland. Then, during high tide, you can get back to relaxing as you bob in the clear blue water’s waves. 

3. Tour the Old-World-Style Hammond Castle

Open from April until the winter, the Hammond Castle Museum is a bit of an anomaly, which is what makes it one of the top things to do in Gloucester, MA. Most visitors to Gloucester don’t expect there would be a European castle on Cape Ann. But indeed, there is one, thanks to John Hays Hammond, Jr., a scientist, inventor, and art connoisseur who had a passion for the art and architecture of old European styles.

Today, Hammond’s Castle is a museum displaying the treasures he collected throughout his travels and showcasing the fine old-world-style architecture he so adored. You can book yourself a tour or take yourself on a self-guided journey into the past. 

But there are also special tours and events to join if you visit at the right time. During the summer and through Halloween, you can take a Thursday Night Spiritualism Tour, a candlelight tour that honors the American Spiritualism Movement, of which Hammond was a firm believer. You’ll learn all about cultural phenomena like spirit photography and more scientific achievements like Hammond’s work with ESP.

Or, if spiritualism isn’t your thing, you can take a Thursday Night Candlelight Tour instead, which is available from September to the end of December. You’ll learn more about the Hammond family itself and about how they built the castle.

During the summer, you can also have your own picnic on the ocean-facing lawn. And for those who love medieval history, the museum offers a lecture on the History of Medieval Arms and Armor.

4. Go Lighthouse Hopping

Up for a drive? Cape Ann is home to five iconic lighthouses, symbols of the area’s maritime history. And if you’re a lover of history and beautiful architecture, taking a lighthouse tour is a must-do thing to do in Gloucester.

To see Annisquam Harbor Lighthouse, head to Wingaersheek Beach and enjoy the view. Over on Ten Pound Island in Gloucester Harbor, you’ll find the aptly named Ten Pound Island Lighthouse. And over in the eastern part of Gloucester, you’ll see the Eastern Point Lighthouse. For the best view of this lighthouse, head to Dog Bar Breakwater.

Just a mile offshore of neighboring Rockport, you’ll discover Thatcher Island, which is home to the Thatcher Island Twin Lighthouses. The south tower has a red light flashing five times every 20 seconds. But the north tower has a steady amber light in honor of those who passed at sea. Also in Rockport, you’ll find the Straitsmouth Island Lighthouse, built upon what is now a 31-acre bird sanctuary.

5. See a Show at the Theater

Gloucester firmly supports the arts, and one of the top things to do in Gloucester, MA, is to take part in the arts and culture of the area. At the Gloucester Stage Company, you’ll find local actors perfecting their craft in intimate productions. This non-profit theater company puts on both contemporary plays and beloved classics inside a century-old warehouse on the Gloucester shore. 

These can’t-miss shows are a perfect way to spend an evening. From rousing comedies to heartbreaking dramas, every performance goes to show how much a night at the theater can affect you, whether you’ll be in tears from laughter or from the emotional performances of these talented actors. 

In addition to their lineup of plays, each year also brings about NeverDark, a series of one-night-only shows performed by world-class actors, comedians, writers, and directors.

6. Sample the Best Ice Cream in Town

Is there anything better than a day at the beach? Yup, it’s a day at the beach with an ice cream in hand. While Gloucester boasts plenty of ice cream shops that’ll help you satisfy your sweet tooth cravings, there’s one shop that you absolutely need to add to your Gloucester bucket list: Holy Cow Ice Cream Cafe.

This award-winning ice cream cafe specializes in ice cream for everyone. Want a childhood favorite mixed into your ice cream? How about an ice cream loaded with Little Debbie’s Cosmic Brownie chunks? Want a Massachusetts staple made in a new way? Try the Boston Cream Pie ice cream. Want to get a little tipsy? Try the whiskey-infused Tipsy Seagull!

It truly is a place for everyone to enjoy. There are plenty of allergen-safe flavors, as well as vegan options. There’s even plant-based peanut butter ice cream you can give to your pooch. So if you’re craving something sweet, you know that Holy Cow can provide you with exactly what you need.

7. Go Whale Watching

Going whale watching is a great way to see the best sights in Gloucester. You can spot whales anytime from May to October, but whale-watching boat captains in the area say that September may be the best month for sightings. 

What can you expect to see? According to Cape Ann Whale Watch, the most commonly spotted creatures are humpback whales, fin whales, minke whales, Atlantic white-sided dolphins, northern right whales, and harbor porpoises. Sei whales, blue whales, sperm whales, and long-finned pilot whales have also been spotted on occasion.

When you take a whale-watching tour with a company like Cape Ann Whale Watch, you’ll be led by naturalists with decades of experience who can take you to the top spots to see whales. In fact, this company so believes that you’ll see a whale that you are invited back on board for free for any number of trips until you do!

8. Take a Dinner Cruise

Want another way to get out on the water? Book your ticket on a dinner cruise. Beauport Cruiselines offers both lunch and dinner cruises that invite you to take in amazing views of downtown Gloucester, Ten Pound Island, Hammond Castle, and so much more. Sip wine on the upper deck as you admire the setting sun, then get ready to dine on upscale cuisine featuring locally-caught seafood. 

If you’re heading to Gloucester with a large group in tow, you can also book a private cruise. While public cruises typically happen during the summer or on special occasions, like their New Year’s Eve Cruise, private cruises are available all year round. When you book a Beauport Cruise, you’re guaranteed entertainment and a delicious meal on every journey.

9. Sample Local Fare On a Food Tour

Cape Ann Foodie Tours are walking culinary and cultural tours through cities located on Cape Ann, and that includes Gloucester. If you love trying the local cuisine everywhere you go, this is one of the best Gloucester activities.

You have two tour options in Gloucester. The first is the original “Taste Gloucester” tour. You’ll make your way on foot through downtown Gloucester as you sample food from five to six vendors. What can you expect to dine on? From local chowder to bacon-wrapped scallops to Italian cannolis, you’ll be in for some serious treats!

Another option is the “Ales & Tales” tour. You’ll be taken to several local Gloucester watering holes, where local fishing captains will thrill you with stories of the sea. From wild storms to run-ins with Russians, you’re guaranteed to be on the edge of your seat. With the fishing industry being so deeply entrenched in Gloucester’s culture, this tour is a perfect way to learn more about what it means to be at sea.

10. Enjoy the Art at Rocky Neck

Just like fishing is such a big part of Gloucester’s community, so too is art. And visiting the Rocky Neck Art Colony is one of the coolest things to do in Gloucester. 

Located on a peninsula in Gloucester’s harbor, Rocky Neck is known for its rich cultural history and spirited community. From plein air artists like Winslow Homer and Childe Hassam to modernists like Milton Avery and Nell Blaine, artists of all kinds have lived on, worked on, and were inspired by Rocky Neck. Throughout the year, you can find everyone from potters to painters to jewelry makers displaying their work here. 

Many of the galleries close for a winter break, so it’s often best to visit during the warmer months. During the summer, you’ll typically see all 16 galleries open, with eclectic pieces bringing vibrancy to the colony. You’ll also find places to eat with gorgeous views, one-of-a-kind boutiques, and a floating tiki bar available for charters.

To get to Rocky Neck during the summer, a water shuttle runs from downtown Gloucester, arriving at the dock 35 minutes past the hour every day from noon to 5 pm. In the spring and fall, the shuttle is only available on weekends and only between noon and 4 pm.

11. Celebrate the Patron Saint of Fishermen

Gloucester has a passionate Italian-American community, and that community is responsible for the creation of St. Peter’s Fiesta, held for five days every June. One of the most fun Gloucester activities, it’s a celebration of Gloucester’s fishing history and faith. St. Peter is the patron saint of all fishermen and was considered the Catholic Church’s first pope. 

This family-friendly festival is filled with all kinds of entertainment for every age. Watch the community parade through the city streets with statues honoring their heritage and history. See the commercial fishing fleet be blessed. During the annual Seine Boat Race, root for the Nina, the Pinta, or the Santa Maria. Take part in the Fiesta 5K. And take your kids to performances of storybooks that come to life. 

But likely the highlight of the festival is the annual Greasy Pole competition, where you’ll see one of the best sights in Gloucester. This truly unique contest takes place 200 feet off Pavilion Beach. 

A 45-foot telephone pole is attached to a platform and extended out over the water, with a red flag nailed to the end. Then, the pole is greased. And so begins an incredible performance where contestants do all that they can to, one by one, take on the pole and capture the flag.

12. Go for a Scenic Hike

Taking a hike offers a great chance for Gloucester sightseeing. And there are plenty of beautiful, scenic hikes to go on throughout the Cape Ann area.

One of the best spots for hiking in Gloucester is Ravenswood Park, which includes a 2.3-mile loop trail perfect for beginner hikers. But there are also more trails available for anyone of any skill level. No matter what season you visit this park, you’re bound to be enthralled by its beauty, from the vibrant leaves in fall to the wildflowers in bloom in the spring.

Over in Mount Ann Park, you can stroll past Dykes Pond and head up the hill to a granite summit, providing you with a stunning view of Cape Ann. Or, for a more seaside walk, you can head to Rafe’s Chasm, which offers two different experiences. New hikers should take the shorter trek to the ocean, where you’ll find clifftop views of the Atlantic. 

But if you’re a more experienced hiker, you may want to try to reach the chasm itself. It’ll require you to climb over several rocks, so you should only do this hike if the weather is fair and there’s no danger of slippery ice or water. But if you decide to take the more challenging road, you’ll be rewarded with breathtaking rock formations.

13. Tour Downtown During a Gloucester Block Party

Visiting downtown Gloucester is a must-do thing to do when you visit this historic little city. You can take the HarborWalk, which is marked by 42 story posts, the first being in St. Peter’s Square. 

The HarborWalk takes you through historical and cultural points around the city, like the beloved Fisherman’s Memorial statue, which honors all the fishermen lost at sea. Throughout downtown, you’ll find art galleries, restaurants, shopping, theaters, museums, historic homes, and so much more. 

There’s never a bad time to do the HarborWalk, but perhaps the best time to visit the downtown area is during the Main Street Block Parties. Occurring Friday nights throughout the summer, you’ll partake in live entertainment from local bands, street performers, children’s activities, and al fresco dining, in addition to seeing all that downtown has to offer throughout the year. 

It’s a perfect way to spend a summer evening with your family and a great way to take in some Gloucester attractions.

14. Explore Tide Pools at Wingaersheek Beach

Good Harbor isn’t the only gorgeous beach you can find in Gloucester. Wingaersheek Beach is a little further off the beaten path, but it’s worth the venture. Running along the Annisquam River and Ipswitch Bay, Wingaersheek Beach is perfect for spending a day soaking up the sun.

One of the best times to visit this beach, called Winga by locals, is during low tide when a long sandbar is exposed alongside different rock formations. As the water retreats nearly a mile, you’ll spot tons of tide pools, with sea creatures going about their days. You’ll need to be careful and leave them to what they’re doing, but you can observe them and marvel at their beauty.

Also on Winga are various larger rock formations, with boulders juxtaposed against the white sand. After you’re done tide-pooling, you can go for a climb and explore the rocky perches. 

15. Peruse the Independent Bookstore

Perhaps one of the best things about Gloucester is that it celebrates its residents and the things that they create. From art galleries to restaurants, you’ll find few places that aren’t locally owned. 

And just like you won’t find many hotel or restaurant chains, you also won’t find many giant, internationally-owned bookstores. Instead, you’ll find quaint, independent bookstores. And visiting these shops is one of the most perfect Gloucester activities if you’re a book lover! 

The Bookstore of Gloucester is one such shop. This bookstore, located on Main Street, has been a part of Gloucester for over 45 years. This bright and cheery shop is a family-owned business dedicated to serving its community. You can even find a section of books from local authors.

Another great place to stop is Dogtown Books. Opened in 1997, this bookstore is run by a couple that believes in the connecting and healing nature of the written word. More than a store, it’s a community meeting place, with events happening all the time that encourage locals and visitors alike to get to know each other and be a part of each other’s journeys.

There you have it! The 15 best things to do in Gloucester, MA. What’s your favorite thing to do in Gloucester?

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