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Rockport and Gloucester MA Things To Do

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Cape Ann Marina | Thing to do in Rockport and Gloucester MA
Cape Ann Marina

The neighboring coastal communities of Rockport and Gloucester, Massachusetts share deep ties to the sea, a rich fishing culture, and spectacular coastal scenery. Our list of favorite things to do in Rockport and Gloucester, MA includes activities that will help you to immerse in the area’s rich maritime culture and rocky coast.

Mile Marker Rum Shack | Things to do in Rockport and Gloucester MA
Mile Marker Rum Shack

Many of the 20 things-to-do on our list are outdoor activities. Rockport and Gloucester are great destinations for families with kids who enjoy beachcombing, wharf-trekking, and spotting the boats from Nat Geo’s hit series, “Wicked Tuna.” See our Rockport and Gloucester MA Travel Guide for information on the weather, hotels, and restaurants at this fun New England travel destination.

Rockport Harbor | Things to do in Rochester and Gloucester MA
Rockport Harbor
Rockport and Gloucester MA Things to Do At A Glance | New England Travel Blog

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Bearskin Neck Jetty | Things to do in Rockport and Gloucester MA | New England Travel Blog
Bearskin Neck Jetty


Discover the Rockport Art Galleries

Rockport is an active artist’s colony. There are many art galleries throughout the village featuring the work of hundreds of artists. Meander among the studios in downtown Rockport along Broadway, Dock Square, Main Street, and Bearskin Neck. Marvel at the creativity and craftsmanship of painters, sculptors, woodworkers, potters, photographers, and jewelry designers who call the area home. Often, the artist will be on hand to discuss their works.

Judi Rolenberg Studio | Rockport Art Galleries | things to do in Rockport MA
Judi Rolenberg Studio
Do a photoshoot at the iconic Rockport Motif No. 1

Motif No. 1 is a red fishing shack at the end of Rockport’s Bradley Wharf. The shack was built in the 1800s to store fishermen’s gear. The artist Lester Hornby dubbed the storage facility “Motif #1” in reference to how often it was painted by area artists. The building is said to be the most photographed and painted building in the world. The shack was featured in the Sandra Bullock movie, “The Proposal,” and a photograph of Motif #1 is in the movie, “Finding Nemo.” You can get great views of Motif #1 from T-Wharf. While in town, do a photoshoot of your family using Motif #1 as the backdrop. Don’t miss the opportunity to capture your own iconic shots.

Motif #1 - Rockport Harbor | Things to do in Rockport MA | New England Travel Blog
Motif #1 - Rockport Harbor
Go on a Whale Watch or Fishing Charter

The Cape Ann peninsula is known for its humpback, minke, and finback whale population. The whale watching season generally runs from April to October. There are several well-established companies offering trips to see these magnificent mammals in their natural habitat. There are also many companies throughout the area offering charter fishing day trips. On either journey, be sure to have a hat, sunscreen, rain gear, and sturdy footwear on hand.

7 Seas Whale Watch | Things to do in Rockport and Gloucester MA
7 Seas Whale Watch
Get lost in the Bearskin Neck Shops

Bearskin Neck is a quarter-mile strip of land off Rockport’s Main Street that juts out into Rockport Harbor. The area has developed into a maze of narrow streets where you will find shingled cape houses crammed full of small shops. Whether the merchandise you seek is a silly summer purchase or a smart artisan treasure, the goods always seem to be just a little bit more unique than you would find in other beach towns.

|Bearskin Neck Shops | Things to do in Rockport MA | New England Travel Blog
Bearskin Neck Shops
Walk Front Beach looking for Sea Shells and Sea Glass

Front Beach is small, scenic beach in the village of Rockport. On the shores of Sandy Bay, the beach is within walking distance of the downtown Rockport. The beach is well-loved by visitors and locals, and is busy year-round (although much more crowded in the summer). This Rockport MA beach has metered street parking, and nearby lots for overflow. Enjoy an afternoon at Front Beach swimming, and searching for sea shells and glass.

Vintage Car - Class of 1971 | Rockport Harbor | New England Travel Blog
Vintage Car - Class of 1971
Visit Halibut Point State Park

Halibut Point State Park is about a 7-minute drive from downtown Rockport. The State Park offers hiking trails through the woods, past an old quarry, and over ledges that run along the ocean. This is a great place to picnic and have a game of frisbee. There is per-car entrance fee. Leased dogs are allowed.

Beach Cottages | Things to do in Rockport and Gloucester MA
Beach Cottages
Get out on the Water with a Sunset Sail

A cruise navigating the islands, lighthouses, and harbors of Cape Ann is a great way to spend the day. It is not unusual on these tours to spot local wildlife including flocks of sea birds, harbor seals, and the occasional whale. Visitors can choose from historic schooners to lightning-fast catamarans. In Rockport Harbor make your way to the Tuna Wharf on Bearskin Neck to book a charter.

Schooner Sails | Things to do in Rockport and Gloucester MA | New England Travel Blog
Schooner Sails
Catch a show at the Shalin Liu Performance Center

If you are a lover of the performing arts (music, dance, theater) check out the Shalin Liu Performance Center’s schedule before heading to Rockport MA. The 300-seat venue features a full schedule of acts. The center’s stunning concert hall has floor to ceiling windows overlooking Sandy Bay. Shalin Liu is within walking distance to the restaurants of downtown Rockport and Bearskin Neck.

Lobster Boat | Rockport Harbor | Rockport and Gloucester Things to do
Lobster Boat
Enjoy fresh Seafood and Beachside Treats

When in Rockport, it’s hard not to plan your day around food. The seafood is fresh and much of the other food is locally sourced. Venues range from swanky dining rooms to take-out shacks. There are many wonderful nautical-themed restaurants offering New England regional favorites; chowder, lobster rolls, and fried clams. There are also Rockport restaurants specializing in hot dogs, ice cream, candy, delis, and much more. Look for a venue with a dining room or deck that has ocean views such as Roy Moore’s Fish Shack or My Place By The Sea Restaurant.

Roy Moore's Fish Shack - 21 Dock Square | Downtown Rockport MA
Roy Moore's Fish Shack
Enjoy a round of Golf

Enjoy a round of golf at the Rockport Golf Club. The semi-private Par 70 course features clubhouse views of Rockport’s Sandy Bay and the Cape Ann Light Station. The golf center has a full-service pro shop and takes tee times online.

Eating out in Gloucester | Things to do in Gloucester MA | New England Travel Blog
Eating out in Gloucester


Visit the Gloucester Fisherman’s Memorial

Visiting the Gloucester Fisherman’s Memorial helps visitors to quickly understand the significance of Gloucester’s fishing culture. Walk along the Stacy Avenue Esplanade to view the monument. The statue features a lone fisher man in oilskin overalls at the wheel of a boat. “The Man at the Wheel” fisherman is positioned to gaze out over Gloucester Harbor. The bronze figure honors 400 years of Gloucester fishermen who have been lost at sea, including the names on the men on the Andrea Gail who were taken in 1991 (from the book and movie The Perfect Storm).

Gloucester Fisherman's Memorial | Things to do in Gloucester MA | New England Travel Blog
Gloucester Fisherman's Memorial

A short distance from The Gloucester Fisherman’s Memorial there is a monument to the families of those lost to the sea. The Gloucester Fishermen’s Wives Memorial features a woman with two children gazing out at Gloucester Harbor waiting for their loved one to return.

 Fishermen's Wives Memorial | Gloucester MA | Cape Ann | New England Travel Blog
Fishermen's Wives Memorial
Walk Gloucester’s Jodrey State Fish Pier

This is one of our favorite places to hang out while in Gloucester. At the 8-acre Jodrey State Fish Pier you are sure to see all kinds of watercraft including huge tankers, commercial fishing boats, yachts, and pleasure boats. On our last trip we saw the Angela + Rose fishing boat chugging into port (the boat used in the Academy Award winning movie, CODA). In this real world setting you can see what’s happening by the seafood processing plant, talk to the locals who are fishing, and watch the trawlers unload their catch. What is not to love?

Fishing Tankers | Jodrey State Fish Pier | Things to do in Gloucester MA
Jodrey State Fish Pier
Stretch your legs at Gloucester’s Stage Fort Park

Stage Fort Park sits on a hill right outside of downtown Gloucester. The gorgeous swath of land overlooks Gloucester Harbor. The park has large stone Visitor’s Center with bathrooms. Onsite there are hiking and biking trails, two beaches (Half Moon and Cressy), a playground, dog park, basketball courts, tennis courts, ball fields, picnic grounds, and panoramic ocean views. This is a great place for couples, families, and anyone who enjoys the outdoors.

Stage Fort Park | Things to do in Gloucester MA | New England Travel Blog
Stage Fort Park
Wander Gloucester’s Main Street & Harbor

Gloucester MA has a charming Main Street. There are book stores, cafes, and antique shops to wander. A block over on the waterfront, visitors will find colorful signs for whale watches and sailing adventures. Stroll behind the buildings on Rogers Street to see the docks where seafood is unloaded off the boat. Trek along Commercial Street to find the Cape Pond Ice Company’s warehouse. The company has been supplying ice to fishermen since the 1800s. In the summer the warehouse offers tours, and there is a company store.

Gloucester Harbor & Waterfront | Cape Ann | Things to do in Gloucester MA
Gloucester Harbor & Waterfront
Follow the Fishermen of Nat Geo's “Wicked Tuna”

Gloucester is the home base of National Geographic’s hit TV series, Wicked Tuna. Visit the marinas and wharves where the captains moor their boats such as the Cape Ann Marina, 7 Seas Wharf, and Smith Cove on Rocky Point. Or, stock up on Wicked Tuna merchandise at area stores. If you are lucky, you might see the crew of a boat unloading their catch or swabbing the decks. On our last trip, we were fortunate to meet Captain Dave Marciano who said ‘hello,’ and treated us to a picture. Bluefin tuna fishing is in season between June and November, but the boats are in port (when not in use) year-round.

Captain Dave Marciano, Wicked Tuna | Things to do in Gloucester MA | New England Travel
Captain Dave Marciano, Wicked Tuna
Tour Hammond Castle Museum

In the 1920s John Hays Hammond, Jr. decided to build a castle in Gloucester, MA. The stone structure is melding of several European architectural styles. For an admission fee, the museum can be explored on your own, or on a tour. The grounds offer stunning views of the Atlantic Ocean. John Hammond dabbled in the arts, science, and technology; and it is fun to see the artifacts he collected.

Hammond Castle Museum | Things to do in Gloucester MA | New England Travel Blog
Hammond Castle Museum
Visit Rocky Neck Art Colony

Enjoy the vibrant Gloucester art scene by visiting the Rocky Neck Art Colony. Rocky Neck is one of the oldest art colonies in America. As you wander, you can chat with many of the artists who are selling their wares. Shop for jewelry, ceramics, wood carvings, watercolors, and so much more. After you finish shopping, stop for a seafood supper at one of the nearby restaurants. The colony bustles in the summer (in the off-season a smaller number of vendors remain open).

Pottery for Sale | Things to do in Rockport and Gloucester MA | New England Travel Blog
Pottery for Sale
Go see Gloucester’s Eastern Point Lighthouse

There is no denying the stark and desolate beauty of Gloucester’s Eastern Point Lighthouse. The Coast Guard runs the lighthouse which cannot be visited. However, across from the lighthouse there is a large lot where visitors can park, and then hike the breakwater that protrudes into the sea. The views are worth the trip.

Bell Tower - Hammond Castle | Things to do in Rockport and Gloucester MA
Bell Tower - Hammond Castle
Relax on Good Harbor Beach

Gloucester’s Good Harbor Beach is our choice for a relaxing day by the sea. There is a nice white sand beach. At low tide beachgoers can hike to Salt Island to explore its coastline. Good Harbor is a full service beach with lifeguards, bathrooms, and concessions (in season). Alcohol is prohibited, and the park has a carry-in-carry-out trash policy. Parking is available for a daily rate, but no cash is accepted onsite. Reservations must be made online.

Stacy Avenue Esplanade | Gloucester Harbor | Things to do in Gloucester MA
Stacy Avenue Esplanade
Complete the Gloucester Harborwalk

Gloucester has put together a harborwalk that winds by the waterfront and through the city’s historic districts. It begins at St. Peter’s Square on Rogers Street and takes visitors by the harbor loop, City Hall, the civic center, and back to St. Peter’s Square. There are educational plaques at stops along the way. The walk is free and can be narrated on a cell phone ap. See for more information.

Lobster Traps - Jodrey State Fish Pier | Things to do in Gloucester MA
Lobster Traps - Jodrey State Fish Pier

You won't run out of things to do in Rockport and Gloucester MA, Laura and Randy

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Cruising past Motif #1 | Rockport Harbor | Things to do in Rockport MA
Cruising past Motif #1


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