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“America’s oldest seaport” is getting ready to reopen along with the rest of the state, just in time for the summer months. There’s never been a better time to rediscover what makes this local community so special.

“It’s worth noting that Gloucester locals love their hometown,” said Jenn Record of the Coast2CoastWithKids blog. “In every single place we visited, we were greeted by friendly, enthusiastic people who were eager to share their stories, their history, and what makes Gloucester special to them. Being from Boston, I’ve always been proud to be New Englanders, but Gloucester raises the bar just a little higher.”

Below is a roundup of some of the many points of interest in Gloucester where you can enjoy the lovely seaside town while maintain safe social distancing measures this summer.

Stage Fort Park

This park is the site of the landing of the first settlers in 1623. Gloucester became the second permanent settlement of the early Puritans in the New World, preceded by Plymouth in 1620. Enjoy the park with over 25 acres of natural beauty including beaches and spectacular views of the harbor and beyond. The Welcoming Center will be open to visitors to assist with brochures, maps, and guides. Stage Fort park is part of the Essex Coastal Scenic Byway.

Ravenswood Park

Explore a shrouded landscape of hemlock groves, a magnolia swamp, and other trees species where you’ll find remnants of Colonial habitation. Ravenswood Park offers 600 acres for solitude and quiet contemplation of nature. The park is a testament to one man’s conservationist philosophy, and to all those who have cared for this special place. With 10 miles of carriage paths and trails that meander through the park, you can find plenty of room to picnic, bird watch, walk, and simply appreciate the outdoors. Children love the Ledge Hill Trail, a two-mile round-trip walk among magical looking, fern-covered boulders.

Wicked Tuna Captains and Vessels

In March 2020, Wicked Tuna premiered its ninth season on National Geographic TV. This “monstah” of a show landed in 2012 and brought viewers around the world to America’s oldest seaport. The show features five local bluefin tuna fishing captains who share their real-world tales and trails of the fishing industry. Fans travel to Gloucester hoping to meet the captains, see their boats, buy Wicked Tuna gear, and see all the city has to offer. You might even catch a glimpse of one of the captains in town—their vessels are docked throughout the inner harbor.

Rocky Neck Art Colony 

America’s oldest continually operating art colony (since 1850), Rocky Neck has played a vital role in America’s art history. Artists such as Fitz Henry Lane, Winslow Homer, John Sloan, Stuart Davis, and Edward Hopper have all captured the light of Gloucester, as many artists do to this day. This quaint neighborhood is a lovely area to stroll, shop, and get up close and personal with many artisans who showcase their work with pride. You can catch some beautiful water views and enjoy an ice cream cone, fresh seafood or a nice iced cold beverage along the way.

Man at the Wheel Statue

The statue, also known as the Gloucester Fisherman Memorial, presides over Stacy Boulevard, at the edge of Gloucester Harbor. Sculpted by artist Leonard Craske and modeled after a local fisherman, the monument was completed in 1925 in honor of Gloucester’s 300th anniversary. It has become the symbol of the city and a place to remember the 10,000+ men lost at sea during the city’s long history. Their names are recorded on memorial plaques surrounding the structure.

Eastern Point

Eastern point is the southern tip of the peninsula between the Atlantic Ocean and the eastern portion of Gloucester Harbor. Poet T. S. Eliot summered here for 20 years (“The sea is all about us,” he wrote in “The Dry Salvages”), and painter Winslow Homer lived at the lighthouse for a time. Come sunset, it’s easy to see why. Get a better look by walking or fishing on Dog Bar Breakwater, a quarter-mile stretch of granite blocks built in 1904 to keep ships from running aground and to shelter Gloucester Harbor from storms, which offers panoramic views of the water and shorelines.

Shopping Gloucester

Gloucester’s charming Main Street features some of your favorite recognized brands, along with many unique locally made items handcrafted by resident artists and craftsmen. Find antiques, art, pottery, books, jewelry, toys, clothing, shoes, home goods, and souvenirs—perfect for that one-of-a-kind item to take home. Food lovers will also delight in the offerings downtown from charming coffee shops to unique olive oils, fresh pasta, chocolate, Italian bread, pastries, and cheese.

Maritime History

Nearly 400 years of history and innovation are written in the streets and buildings of this town. Wander the downtown Harbor Walk or visit Maritime Gloucester (Phase 3) to learn more about Gloucester’s past and present as one of America’s most important fishing towns. Walk along the harbor to view the working vessels and pleasure craft. Or get on the water with your own vessel or a chartered fishing excursion or water shuttle. Being a mariner in Gloucester allows you to view the city and coastline from a new perspective.


Find the best views from every angle in town. The 1.2 mile path traverses through town between the Gloucester House and Stage Fort Park. Make sure to stop at the Fisherman’s Memorial and the Fishermen’s Wives’ Memorial. The walk is defined by 42 granite pillars which tell the stories of important people and events of Gloucester’s history. Bookmark this link, which has a list of public restrooms open during business hours. If you are looking for more outdoor fun at the water, check out Good Harbor and Wingaersheek Beaches, both accessible to the public and with facilities that include restrooms, showers, and lifeguards.

Outdoor Dining

Here are a few restaurants that are providing outdoor dining that coincides with the Massachusetts regulations as we enter Phase 2.

Minglewood Harborside has for large portions, several gluten free choices, at least 12 sushi options, tons of open space for families, and attentive service.

Mile Marker One is a beautiful setting right along the Annisquam River. You can sip a cocktail and enjoy their menu selections while watching the activity on the river. 

Castle Manor Inn Restaurant on Essex Avenue offers outdoor dining under a tent surrounded by the perfectly groomed landscaping of the Inn. Laura and Don are gracious hosts who will make you feel right at home!

Blue Collar Lobster has downtown water views and great seafood. The restaurant is walking distance to many shops, museums, boat tours, and the Harborwalk path. And if you see Lenny, whose family has owned the restaurant since it opened in 1957, ask him to pull up a seat—he’ll be glad to share local folklore and history.

1606 Restaurant at the Beauport Hotel for outdoor seating on the waterfront and unique takes on traditional favorites. The stunning views are the perfect ambience for date night and special celebrations. The outdoor patio has a large deck with comfortable seating, and an outdoor fireplace and blankets are available should your evening get cooler.