If you’re looking to explore a charming coastal New England city, Gloucester, Massachusetts is the place to go. Gloucester was founded in 1642 and has had an important role in the fishing industry for centuries. There’s more to this cape city than fishing, though. It’s filled with history, culture, and seaside fun. There’s a lot to choose from, so where do you even start? Here are some of the best things to do in Gloucester MA on your next trip.
PS if you’re looking for things to do in Gloucester MA this weekend or what to do in Gloucester today, check out this local events calendar to see what will be happening during your Gloucester trip.
Things to Do in Gloucester MA
Visit Good Harbor Beach
Gloucester is known for its incredible beaches, and one of the best to visit is Good Harbor Beach. Good Harbor Beach is located along Thatcher Road and is known for its white sand and rocky coastal views. Bring your beach towel, boogie board, and other beach accessories to enjoy a beautiful day on this New England beach. Afterward, you can get a sweet treat at Ro’s Harbor Scoops or grab a bite to eat at Charlie’s Place — both places are just down the road from the beach.
Make sure you bring money for parking when visiting Good Harbor Beach.
Tour Hammond Castle Museum
One of the coolest things to do in Gloucester, Massachusetts is to tour the Hammond Castle Museum. This European-style castle was built in the late 1920s by John Hays Hammond, Jr. — a scientist and inventor who appreciated old European architecture. He incorporated designs from several eras together to create a truly unique structure that has incredible views of the Massachusetts coast.
Museum visitors can tour the grounds and admire the medieval artifacts and the castle’s unique architecture. You can tour the castle on your own or go on a guided tour. You could even host a special event at the castle. A beautiful castle + a gorgeous view of the ocean = an event you (and your guests) will never forget.
Hang at Stage Fort Park
Stage Fort Park is an important historic park in Gloucester that is the site that the first Gloucester settlers arrived, and today it is an important community gathering space. Not only are two of Gloucester’s beautiful beaches located there (Half Moon and Cressy’s), but there’s a large playgrounds for the kids, a basketball court, tennis court, baseball field, sand volleyball court, and more.
Stage Fort Park hosts many community events and festivals throughout the year, so this lovely coastal park is a great place to visit in Gloucester to get a good feel for the community.
Go Whale Watching
One of the signature things to do in Gloucester, Massachusetts is to go whale watching. Whales are regularly seen along Cape Ann, and you can schedule a time to hop on a boat and see them in their natural habitat. Whale watching season typically runs April through October, but that could vary depending on which whale watching tour you book.
Be sure to pack things like an extra sweatshirt or jacket, sunglasses, and sunscreen when you go on a whale watching tour. You should also wear closed-toe shoes that you’re comfortable walking and standing in. There are multiple companies you can book a whale watching tour through, including Cape Ann Whale Watch and 7 Seas Whale Watch.
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Visit Eastern Point Lighthouse
No Gloucester Massachusetts trip would be complete without a visit to Eastern Point Lighthouse! This gorgeous MA lighthouse perches proudly on the rocky coast, with the lighthouse that stands today having been built in 1848. A long breakwater juts out into the water and the views all around this Gloucester lighthouse are stunning. If you’re looking for a great place to photograph at sunset in Gloucester MA, consider Eastern Point Lighthouse.
See Gloucester Fisherman’s Memorial
This is one of those things to do in Gloucester that gives you a glimpse into the history and spirit of the city. The Gloucester Fisherman’s Memorial, also known as “The Man at the Wheel”, is an eight-foot bronze statue of a fisherman that pays tribute to the thousands of fishermen lost at sea during Gloucester’s existence. The fisherman looks out over Gloucester Harbor.
To see this symbol of Gloucester and its history, head to the south side of Stacy Boulevard. You’ll be one of the thousands of people who visit The Man at the Wheel each year to see this piece of Gloucester history and pay tribute to the fishermen lost at sea.
When I visited this spot, I got chills. Most meaningful to me was to see the names of those lost in the early 90’s, events which are retold in the book and film The Perfect Storm. If you’ve seen that movie or read that book (both of which are excellent and heart-rending) to see these names on the memorial drives home the tragic loss this community must have felt.
The Gloucester Fishermen’s Wives Memorial
Another highly evocative Gloucester attraction is the Gloucester Fishermen’s Wives Memorial, honoring the families left behind when The Man at the Wheel is lost at sea. This stirring memorial features a mother and her two children looking out to sea, scanning the harbor for their missing family member.
Visit Wingaersheek Beach
If you’re an avid beach-goer, you have to make time to visit Wingaersheek Beach in Gloucester. You’ll find this gorgeous beach along the Annisquam River and Ipswich Bay with locals and tourists alike walking in the sand, looking for sand dollars, and spotting hermit crabs.
This Gloucester beach is located at the end of Atlantic Street, and you’ll need to pay to park. There’s a “carry in-carry out” policy at the beach, so if you have trash, make sure you don’t leave it at the beach and get rid of it properly.
See a Show at the Gloucester Stage Theater Company
Professional theater on an intimate stage in Cape Ann’s Gloucester? Absolutely one of the top things to do in Gloucester, especially if you’re looking for a nice evening out in town. Pair it with a lovely dinner and you’re set for a romantic date night in Gloucester. You can check Gloucester Stage Theater Company’s season lineup here!
Tour Beauport, the Sleeper-McCann House
One of the best things to do in Gloucester, Massachusetts is to visit Beauport, the Sleeper-McCann House. This incredible mansion is a National Historic Landmark that has more than 40 rooms and an incredible view overlooking Gloucester Harbor. It was the summer home of the United States’ first interior designers, Henry Davis Sleeper. He used the home to entertain guests and as a professional showcase. After his death, the home was bought by the McCanns.
There’s a reason why this house is a national treasure. No two rooms in the mansion are the same, which means you’ll have a completely different experience in each room. The mansion is dazzling, beautiful, and a place unlike any other. You can visit the house for in-person events or explore the home through digital tours.
Visit Cape Pond Ice Company
If you’re looking for a historic place to cool down in Gloucester, one of the best places to visit is Cape Pond Ice Company. Located along Gloucester’s historic waterfront, the company was founded in 1848 under the name Gloucester Co. A blacksmith named Nathaniel R. Webster saw the need for supplying the fresh fish industry with ice, and thus, started a company that saw incredible success.
Today, Cape Pond Ice Company stands as a local company with great pride in its history. Narrated tours of the ice company are available from June through August. Bring a jacket, though — it is an ice company, after all!
Stay at Beauport Hotel Gloucester
If you’re looking for a place to stay in Gloucester that will pamper you a bit, Beauport Hotel Gloucester is it! With a coastal modern ambiance and luxury touches everywhere you turn, this oceanfront hotel is the perfect place to stay for a romantic couples trip to Gloucester. There’s a rooftop pool and bar, so if you’re planning your Gloucester trip for summer, there’s really no better choice for an impressive place to stay in Gloucester MA.
Click Here to Check Prices & Book!
Stroll Through Downtown Gloucester
If you’re looking for low-key (but still super fun) things to do in Gloucester, one thing you can do is stroll through the downtown area. Downtown Gloucester has a ton of great small businesses and delicious restaurants to check out. If you’re a fan of seafood, eating at a downtown Gloucester restaurant is a must — the seafood is fresh off the boat.
If you like to go out at night, there are plenty of bars and taverns to grab a drink at. Downtown Gloucester is also beautiful, so if the weather’s nice, you can take a lovely stroll and admire the coastal city.
Visit The Cultural Center at Rocky Neck
Gloucester has an art scene that’s a must-see for locals and tourists alike, and seeing the local art scene is one of the most interesting things to do in Gloucester. One place you must visit is the Cultural Center at Rocky Neck. The center hosts rotating exhibitions and events, and people can also rent it out for events.
After you visit the center, you can take a stroll down the Rocky Neck Art Colony. It’s one of the oldest working art colonies in the United States and has been established for more than 150 years. You can stroll along the area and see artists selling paintings, jewelry, sculptures, and other unique gifts. You can also try one of the fabulous restaurants in the area and get a good meal with an even better view.
Rent a Boat
Gloucester is a coastal city, so one of the best things to do in Gloucester is to rent a boat and go out on the water. There are numerous places where you can rent a boat, so it’s best to do your research and look up the requirements for renting a boat at each location. You can rent boats based on their size and how many people they hold, so make sure you know how many people will join you on your outing.
You could take a leisure cruise around the water or go fishing when you rent one of these boats. Some boat rental places even offer rental fishing gear so you don’t have to buy your own just for one trip. Make sure you know Massachusetts boating laws and take the proper safety measures before you set sail.
Gloucester is an incredible city with plenty of history and culture to explore. Its coastal charm and thriving local attractions will help you jam-pack your Gloucester trip with unforgettable activities ranging from whale watching to beach-going. Make sure you take time to capture all the incredible moments and soak in the experience of visiting this beautiful New England city. You’ll be planning your next trip to Gloucester in no time.
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Amy Hartle is the owner and editor of New England With Love, a comprehensive resource for travel in the New England region. Amy lived in Vermont for 15 years, attended Plymouth State University in New Hampshire, and continues to travel regularly around the entire New England region. On this site, Amy aims to share her love of New England and help you to have the best possible adventures!
Amy has been a full time blogger since 2012, and is also the publisher of Two Drifters, where she writes about couples travel and relationships, as well as Let’s Adventure Baby, a family travel site. When not traveling the world or creating epic blog content, Amy can be found cuddling with her husband, son, and cats, & drinking a maple latte.