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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 located just 40 miles north of Boston. Known for its rich history, artistic community, and stunning natural beauty, Gloucester has something to offer everyone. Whether you’re a foodie looking to indulge in fresh seafood, an art lover seeking inspiration, or an outdoor enthusiast looking for 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, showcasing the work of local artists and artisans. You can explore the art scene by taking a walking tour of downtown Gloucester, where you’ll 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 beautiful beaches and natural scenery. Good Harbor Beach, located along Thatcher Road, is a must-visit destination with its white sand and rocky coastal views. You can also explore the nearby Halibut Point State Park, which offers hiking trails, scenic views, and a historic quarry. And of course, no trip to Gloucester is complete without indulging in some fresh seafood. The town is famous for its lobster, cod, and other local catches, which you can enjoy at one of the many seafood restaurants and markets.

Artistic Gloucester

Gloucester is known for its vibrant arts scene, and there are plenty of ways to experience it firsthand. Here are a few places you won’t want to miss.

Rocky Neck Art Colony

If you’re looking for 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, as well as artifacts from Gloucester’s maritime past. And if you’re 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 unique 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, including rare and vintage titles. And don’t miss the galleries along Main Street, where you can browse works by local artists and maybe even pick up a piece to take home.

Whether you’re a seasoned art lover or just looking for something new and exciting to do, Gloucester won’t 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 are sure to impress. Here are three must-see landmarks that you won’t want to miss:

Hammond Castle Museum

If you’re a fan of medieval castles and artifacts, then 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’ll be transported back in time as you explore the castle’s many rooms and admire its impressive architecture.

Beauport, The Sleeper-McCann House

For a glimpse into the life of one of Gloucester’s most prominent citizens, be sure to visit Beauport, The Sleeper-McCann House. Built in 1907 by Henry Davis Sleeper, this beautiful house is filled with art and antiques from around the world. You’ll be amazed by the intricate details and beautiful 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 beautiful 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’s a touching tribute to the sacrifices made by the families of Gloucester’s fishermen.

So, there you have it – three of Gloucester’s most fascinating historic landmarks. Whether you’re a history buff or just looking for a fun and educational day out, these landmarks are sure to impress.

Beaches and Natural Beauty

When it comes to natural beauty, Gloucester has it all – from stunning beaches to breathtaking views of the ocean. Here are some of the best places to soak up the sun and enjoy the great outdoors in Gloucester:

Good Harbor Beach

Ah, Good Harbor Beach. The quintessential summer destination. With its soft white sand and crystal-clear water, it’s no wonder this beach is a local favorite. Whether you want to swim, sunbathe, or just relax with a good book, Good Harbor Beach has got you covered.

Wingaersheek Beach

Looking for a beach that’s a little more off the beaten path? Look no further than Wingaersheek Beach. This hidden gem is tucked away on the north shore of Gloucester, and it’s the perfect place to escape the crowds and enjoy some peace and quiet. Plus, the views of the ocean are absolutely stunning.

Salt Island

If you’re looking for a truly unique natural experience, head over to Salt Island. This small island is located just off the coast of Gloucester, and it’s a great place to explore the natural beauty of the area. Whether you want to hike, swim, or just take in the views, Salt Island is the perfect destination for nature lovers.

So, whether you’re looking for a 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’re a seafood lover, Gloucester is the place to be. With its location on the coast, Gloucester has some of the freshest seafood around. And what better way to experience it than on a foodie tour? Here are some of the best foodie tours in Gloucester that you won’t 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’re looking for fresh seafood, Connolly Seafood is the place to go. This family-owned and operated business has been serving up some of the best seafood in Gloucester for over 40 years. From lobster to scallops, Connolly Seafood has it all. And if you’re not sure what to get, the friendly staff will be more than happy to help you choose.

Turners Seafood

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

So whether you’re a seafood aficionado or just looking for a fun foodie tour, Gloucester has something for everyone. Don’t miss out on the chance to sample some of the freshest seafood around.

Whale Watching and Fishing

If you’re in Gloucester, Massachusetts, you can’t miss out on the chance to go whale watching and fishing. It’s one of the most fun and exciting things to do in the area. Here are some of the best options for whale watching and fishing tours in Gloucester:

Cape Ann Whale Watch

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

7 Seas Whale Watch

7 Seas Whale Watch is another great option for whale watching in Gloucester. The tour guides are friendly and informative, and they’ll make sure you see as many whales as possible. You’ll 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’re out on the water.

Fishing Port Tour

If you’re interested in the fishing industry in Gloucester, you should take a fishing port tour. You’ll get to see the fishing boats coming in and out of the harbor, and you’ll learn about the history of fishing in the area. You’ll 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, you can book a private charter for whale watching or fishing. You’ll have the boat all to yourself, so you can customize the tour to your liking. Plus, you’ll get to spend quality time with your friends or family without any distractions.

Overall, whale watching and fishing are some of the best things to do in Gloucester, Massachusetts. Whether you’re interested in seeing whales up close or learning about the fishing industry, there’s something for everyone. So, grab your camera and get ready for an adventure you’ll never forget!

Lighthouses and Scenic Views

Gloucester is home to some of the most beautiful lighthouses and scenic views in Massachusetts. Whether you’re a history buff or just looking for a picturesque spot for your Instagram feed, the lighthouses of Gloucester are a must-visit. Here are two lighthouses that you should definitely check out:

Eastern Point Lighthouse

Built in 1890, the Eastern Point Lighthouse is a classic New England beacon with red-roofed white ancillary buildings, located 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 can enjoy panoramic views of the harbor and the Atlantic Ocean.

Don’t forget to bring your camera, because the Eastern Point Lighthouse is one of the most photographed lighthouses in the world. You can also take a tour of the lighthouse and learn about its fascinating history.

Thacher Island Lighthouse

Thacher Island is home to two lighthouses: the North Tower and the South Tower. The North Tower was built in 1771, making 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, you can take a boat tour from Gloucester Harbor. Once you arrive, you can hike to the top of the island and enjoy stunning views of the Atlantic Ocean. You can also take a tour of the lighthouses and learn about their history.

Both Eastern Point Lighthouse and Thacher Island Lighthouse are must-visit spots in Gloucester. So, grab your camera and head out to these beautiful lighthouses for a scenic adventure you won’t forget.

Live Music and Entertainment

Looking for some live music and entertainment while in Gloucester? You’re in luck, because this charming town has plenty of options to choose from!

Downtown Gloucester

If you’re 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 has a great selection of craft beers and cocktails, as well as live music on the weekends.

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

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’s not hard to see why. In addition to their delicious seafood dishes, they also offer live music on select nights throughout the summer.

Their outdoor deck is the perfect spot to soak up some sun and enjoy the sounds of local musicians. Plus, they have a great selection of beer and wine to choose from.

No matter where you go, you’re sure to find some great 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’re 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 has plenty of attractions to keep you busy, but if you’re looking to venture out a bit, there are some great 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’re feeling really adventurous, take a day trip up to Maine and indulge in some fresh lobster!

Where can I find the best seafood in Gloucester?

Ah, the age-old question! There are plenty of great seafood restaurants in Gloucester, but if you’re looking for the freshest catch, head to the docks and buy directly from the fishermen. You can’t get any fresher than that! And if you’re 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 vibrant arts scene, and there are plenty of events to celebrate it. Check out the Gloucester Schooner Festival, where you can see some of the most beautiful 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’s never a dull moment in Gloucester!

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