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Gloucester, Massachusetts: The Best & Fun Things To Do + Places To Visit (According to Someone Who’s Never Been There)

Welcome to Gloucester, Massachusetts, a charming coastal town just 40 miles north of Boston. Known for its long history, its artistic community and its natural scenery, Gloucester runs a version for everyone. Here to eat fresh seafood, to find artistic inspiration, or to get outdoors after an adventure, Gloucester has it all.

One of the highlights of Gloucester is its thriving artistic community. The town is home to numerous galleries and studios showing the work of local artists and artisans. You can work through the art scene on a walking tour of downtown Gloucester, where you will find everything from contemporary paintings to handcrafted jewelry. You can also visit the Cape Ann Museum, which features exhibits on the town’s maritime history and art.

Gloucester is also known for its beaches and its natural scenery. Good Harbor Beach, along Thatcher Road, belongs on any list with its white sand and rocky coastal views. You can also explore the nearby Halibut Point State Park, which runs hiking trails, scenic views and a historic quarry. And of course, no trip to Gloucester is complete without working through some fresh seafood. The town is famous for its lobster, cod and other local catches, which you can eat at one of the many seafood restaurants and markets.

Artistic Gloucester

Gloucester is known for its lively arts scene, and there are plenty of ways to take it in firsthand. Here are a few places you will not want to miss.

Rocky Neck Art Colony

Check the forecast before you commit to anything on the water. Cape Ann Whale Watch and 7 Seas Whale Watch both run out of the harbor, and both are at the mercy of the same North Atlantic. Good Harbor Beach and Wingaersheek Beach both need sun. The Cape Ann Museum and Hammond Castle Museum are the wet-day answer. Gloucester sits 40 miles north of Boston, so you can leave the decision late.

If you are after a dose of inspiration, head to the Rocky Neck Art Colony. This historic neighborhood has been home to artists for over a century, and you can still see their influence today. Take a stroll down the narrow streets and admire the colorful cottages and studios. You might even catch a glimpse of an artist at work.

Cape Ann Museum

For a deeper dive into the art and history of Gloucester, visit the Cape Ann Museum. Their collection includes works by local luminaries like Fitz Henry Lane and Winslow Homer, along with artifacts from Gloucester’s maritime past. And if you are lucky, you might catch one of their special exhibitions, which cover everything from contemporary art to vintage postcards.

Galleries and Independent Bookstores

Gloucester is home to a number of galleries and independent bookstores, each with its own flavor. Check out The Bookstore of Gloucester for a cozy atmosphere and a carefully curated selection of books. Or head to Dogtown Books for a more eclectic assortment, rare and vintage titles included. And do not miss the galleries along Main Street, where you can browse works by local artists and maybe even pick up a piece to take home.

Seasoned art lover or simply after something new and exciting to do, Gloucester will not disappoint. So grab your sketchbook or your camera and get ready to be inspired.

Historic Landmarks

Gloucester, MA is home to a number of historic landmarks that will impress. Here are the landmarks you will not want to miss:

Hammond Castle Museum

If you are a fan of medieval castles and artifacts, the Hammond Castle Museum is the place for you. Built in the late 1920s by John Hays Hammond Jr., this European-style castle is filled with fascinating exhibits and artifacts from the medieval period. You will be moved back in time as you work through the castle’s many rooms and admire its architecture.

Beauport, The Sleeper-McCann House

For a glimpse into the life of one of Gloucester’s more prominent citizens, visit Beauport, The Sleeper-McCann House. Built in 1907 by Henry Davis Sleeper, this house is filled with art and antiques from around the world. You will be amazed by the intricate details and the craftsmanship that went into every aspect of this historic home.

Fishermen’s Wives Memorial

Gloucester has a long and proud history as a fishing community, and the Fishermen’s Wives Memorial pays tribute to the brave women who supported their husbands and sons as they went out to sea. This monument features a bronze statue of a woman looking out to sea, with the names of Gloucester’s lost fishermen inscribed on the base. It is a touching tribute to the sacrifices made by the families of Gloucester’s fishermen.

So, there you have it, three of Gloucester’s more fascinating historic landmarks. History buff or simply after a fun and educational day out, these landmarks will impress.

Beaches and Natural Beauty

On natural scenery, Gloucester has it all, from the beaches to the long views out over the ocean. Here are some of the stronger places to soak up the sun and take in the great outdoors in Gloucester:

Good Harbor Beach

Ah, Good Harbor Beach. The quintessential summer destination. With its soft white sand and clear water, it is no wonder this beach is a local favorite. Swimming, sunbathing or simply settling in with a good book, Good Harbor Beach has got you covered.

Wingaersheek Beach

Looking for a beach that runs a little quieter? Wingaersheek Beach is the answer. This quiet find is tucked away on the north shore of Gloucester, and it suits escaping the crowds exactly. Plus the views of the ocean hold up on any day.

Salt Island

If you are after a genuinely unusual natural experience, head over to Salt Island. This small island sits just off the coast of Gloucester, and it is a strong place to work through the natural side of the area. Hiking, swimming or simply taking in the views, Salt Island suits nature lovers exactly.

So, classic New England beach experience or a more secluded natural retreat, Gloucester has got you covered. So pack your sunscreen, grab your beach towel and get ready to soak up the sun.

Seafood and Foodie Tours

If you are a seafood lover, Gloucester is the place to be. With its location on the coast, Gloucester carries some of the freshest seafood around. And what better way to take it in than on a food tour? Here are some of the stronger food tours in Gloucester that you will not want to miss.

Main Street Foodie Tour

Take a stroll down Main Street and indulge in some of the best seafood in Gloucester. The Main Street Foodie Tour will take you to some of the top restaurants in the area, where you can sample everything from lobster rolls to clam chowder. And don’t forget to save room for dessert. You’ll also get to explore the historic district and learn about the town’s rich history.

Connolly Seafood

If you are after fresh seafood, Connolly Seafood is the place to go. This family-owned and operated business has been serving some of the stronger seafood in Gloucester for over 40 years. Lobster through to scallops, Connolly Seafood has it all. And if you are not sure what to get, the friendly staff will be more than happy to help you choose.

Turners Seafood

Turners Seafood belongs on any seafood lover’s list. This award-winning restaurant has been serving fresh seafood since 1994. From the classic New England clam chowder to the lobster mac and cheese, Turners Seafood has a version for everyone. And if you are in the mood for something a little different, try the seafood paella or the lobster risotto.

So, seafood aficionado or simply after a fun food tour, Gloucester has a version for everyone. Do not miss the chance to sample some of the freshest seafood around.

The North Tower on Thacher Island went up in 1771. The South Tower replaced a wooden one that a storm took out in the first place, which tells you most of what you need to know about the weather here. Getting out to the island means a boat from Gloucester Harbor and then a hike to the top of it. Eastern Point Lighthouse is the easy one. The Fishermen’s Wives Memorial carries the names of the men the sea kept for itself.

Whale Watching and Fishing

If you are in Gloucester, Massachusetts, do not miss the chance to go whale watching and fishing. It is one of the more fun and exciting things to do in the area. Here are some of the stronger options for whale watching and fishing tours in Gloucester:

Cape Ann Whale Watch

Cape Ann Whale Watch is one of the more popular whale watching tours in Gloucester. You get to see humpback whales, fin whales, minke whales and more. The tour guides are knowledgeable and entertaining, and they will make sure you have a strong time. Plus the boat is comfortable and spacious, so you can settle in and enjoy the ride.

7 Seas Whale Watch

7 Seas Whale Watch is another strong option for whale watching in Gloucester. The tour guides are friendly and informative, and they will make sure you see as many whales as possible. You get to see humpback whales, fin whales, minke whales and more. The boat is also equipped with a snack bar, so you can grab a bite to eat while you are out on the water.

Fishing Port Tour

If the fishing industry in Gloucester interests you, take a fishing port tour. You get to see the fishing boats coming in and out of the harbor, and you pick up the history of fishing in the area. You also get to see the fish auction, where the fish are sold to local restaurants and markets.

Private Charter

If you want a more personalized experience, book a private charter for whale watching or fishing. You have the boat all to yourself, so you can shape the tour to your liking. Plus you get an unhurried day with your friends or family without any distractions.

Overall, whale watching and fishing are among the stronger things to do in Gloucester, Massachusetts. Seeing whales up close or picking up the fishing industry, there is a version for everyone. So grab your camera and get ready for an adventure that stays with you.

Lighthouses and Scenic Views

Gloucester is home to some of the finer lighthouses and scenic views in Massachusetts. History buff or simply after a picturesque spot for your Instagram feed, the lighthouses of Gloucester belong on your list. Here are two lighthouses to check out:

Eastern Point Lighthouse

Built in 1890, the Eastern Point Lighthouse is a classic New England beacon with red-roofed white ancillary buildings, on a rocky peninsula at the entrance to Gloucester Harbor. Despite signs reading Private Road, visitors are allowed to drive to the parking lot. From there you can take a short walk to the lighthouse, where you get panoramic views of the harbor and the Atlantic Ocean.

And do not forget to bring your camera, because the Eastern Point Lighthouse is one of the more photographed lighthouses in the world. You can also take a tour of the lighthouse and pick up its fascinating history.

Thacher Island Lighthouse

Thacher Island is home to a pair of lighthouses, the North Tower and the South Tower. The North Tower was built in 1771, which makes it the oldest lighthouse in the United States still in operation. The South Tower was built in 1861 to replace the original wooden tower, which had been destroyed by a storm.

To get to Thacher Island, take a boat tour from Gloucester Harbor. Once you arrive, you can hike to the top of the island and take in the long views of the Atlantic Ocean. You can also take a tour of the lighthouses and pick up their history.

Both Eastern Point Lighthouse and Thacher Island Lighthouse belong on any list in Gloucester. So grab your camera and head out to these lighthouses for a scenic adventure that stays with you.

Live Music and Entertainment

Looking for some live music and entertainment while in Gloucester? You are in luck, because this charming town runs plenty of options to choose from.

Downtown Gloucester

If you are in the mood for a night out on the town, head to Downtown Gloucester. This lively area is home to several bars and restaurants that regularly feature live music. One popular spot is Minglewood Tavern, which carries a strong selection of craft beers and cocktails, along with live music on the weekends.

Another strong option is the Rhumb Line, which has been a staple in Downtown Gloucester for over 25 years. They run live music every night of the week, with a focus on jazz and blues. Plus their outdoor patio suits a drink and some tunes on a warm summer evening exactly.

Gloucester House

For a more laid-back atmosphere, check out the Gloucester House. This waterfront restaurant and bar has been a local favorite for over 60 years, and it is not hard to see why. Alongside their seafood dishes, they also run live music on select nights through the summer.

Their outdoor deck suits soaking up some sun and taking in the sounds of local musicians. Plus they carry a strong selection of beer and wine to choose from.

Wherever you go, you will find strong live music and entertainment in Gloucester. So grab a drink, sit back and enjoy the show.

Frequently Asked Questions

What’s the best way to spend an evening in Gloucester?

Well, you have a few options here. You could take a romantic stroll along the harbor, watch the sunset over the ocean, or grab a drink at one of the local bars. If you are feeling adventurous, you could even try your luck at catching some lobsters with the locals. Just be sure to bring your sea legs and a sense of humor.

What are some must-see attractions near Gloucester, MA?

Gloucester runs plenty of attractions to keep you busy, but if you are looking to venture out a bit, there are some strong options nearby. Check out the historic town of Salem, famous for its witch trials and spooky atmosphere. Or head up to Rockport, a charming seaside village with plenty of art galleries and cute shops. And if you are feeling really adventurous, take a day trip up to Maine and work through some fresh lobster.

Where can I find the best seafood in Gloucester?

Ah, the age-old question. There are plenty of strong seafood restaurants in Gloucester, but if you are after the freshest catch, head to the docks and buy directly from the fishermen. You cannot get any fresher than that. And if you are feeling really brave, try your hand at cooking up your own seafood feast. Just be sure to invite us over.

What are the most popular events happening in Gloucester, MA?

Gloucester is known for its lively arts scene, and there are plenty of events to celebrate it. Check out the Gloucester Schooner Festival, where you can see some of the finer ships in the world. Or head to the Rocky Neck Art Colony for their annual art walk. And of course, no visit to Gloucester is complete without checking out the St. Peter’s Fiesta, a wild and crazy celebration of the city’s fishing heritage.

What’s the funniest thing that’s ever happened in Gloucester?

Oh boy, where do we even begin? There was that time a seal jumped onto a fishing boat and stole a fisherman’s lunch. Or the time a group of tourists mistook a statue of a fisherman for a real person and tried to take a selfie with him. And who could forget the time a rogue wave soaked a group of unsuspecting beach-goers? Trust us, there is never a dull moment in Gloucester.

Frequently asked questions about Gloucester, Massachusetts

Which Gloucester beach is the quieter one?

Wingaersheek Beach, on the north shore. It sits away from the crowds in a way Good Harbor Beach does not, and the water is calmer for it. Good Harbor is the classic one, white sand and rocky coastal views off Thatcher Road, and it fills up on any warm day. Salt Island sits just off the coast for anyone who would rather hike than lie down. All three of them turn on the weather.

Which Gloucester museum is worth a rainy day?

Cape Ann Museum, comfortably. It holds Fitz Henry Lane and Winslow Homer alongside artifacts from Gloucester’s maritime past, and the special exhibitions rotate. Hammond Castle Museum is the stranger option, a European-style castle built in the late 1920s and stuffed with medieval artifacts. Beauport, The Sleeper-McCann House is the third, built in 1907 and filled with art and antiques from around the world. Any of them beats a wet beach.

Which lighthouse near Gloucester is easier to reach?

Eastern Point Lighthouse, without much argument. You can drive to the parking lot despite the private road signs, and it is a short walk from there to the light. Thacher Island needs a boat out of Gloucester Harbor and a climb once you land. The North Tower there dates from 1771 and is the oldest still working in the country. One is an afternoon and the other is a day.

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