Plan a Fall Trip to Gloucester, MA: Things to Do, See & Eat by the Coast

August 18, 2025 / Good to Know, Things to Do & See

Located less than an hour from Boston and just a quick drive or train ride from Salem, Gloucester offers a relaxing and scenic escape that’s easy to reach but feels a world away. Hop on the commuter rail, take CATA around town, or stroll around town on foot — it’s all part of the fall fun.

From art walks to harbor tours, cozy restaurants to coastal hikes, and so much more, here’s how to spend a fall day (or weekend) in America’s oldest seaport.

Take in the Fall Views from Land or Sea

Get out on the water for a look at Cape Ann’s stunning coastline before winter rolls in. Cape Ann Whale Watch and 7 Seas Whale Watch continue running trips into the fall — the perfect time to see the whales.  You can also explore the Essex River marshes with Essex River Cruises, or hop aboard a historic schooner sail with the Schooner Adventure, Schooner Thomas E. Lannon, or Maritime Heritage Charters.

Prefer to stay on land? Greenbelt, Essex County’s Land Trust offers miles of hiking trails with coastal views and changing foliage. For a more leisurely round of fall fun, Harbor 9 Golf & Sports Bar is open year-round with indoor golf simulators and special events, and Cape Ann Lanes is a go-to for candlepin bowling, arcade games, beer, pizza, and more.

Explore Gloucester’s Arts & Culture Scene

Fall is the perfect season for arts lovers to explore Gloucester’s two Cultural Districts — Harbortown and Rocky Neck Art Colony — as well as the thriving creative scene across Cape Ann.

Plan your visit around Cape Ann Plein Air, a weeklong celebration of outdoor painting, or stop by Cape Ann Museum Green to experience rotating exhibits, historic collections, a Contemporary Art Wetu, and more. On Rocky Neck, browse local galleries and check out current exhibitions at the Cultural Center and Cove Gallery, just to name a few.

Nearby in Rockport, don’t miss Rockport Art Association & Museum, Coastal Locals, and Rockport Music, all located close to the restaurants, shops, and galleries on Bearskin Neck. For more local art around the area, check out Cape Ann Artisans‘ seasonal tours and directory of nearby artists.

Taste Fall Flavors Around Cape Ann

Settle into a cozy booth or waterfront deck for comfort food, fresh seafood, or seasonal cocktails here in Gloucester and throughout Cape Ann. Whether you’re looking for pumpkin spice, candied apples, or traditional New England fare, local restaurants are offering something for every taste this fall.

Head over to Blue Collar Lobster to pick up a lobster roll, fried seafood plate, or poke bowl with a handcrafted cocktails and views of Gloucester’s working waterfront. Nearby, Minglewood Harborside serves up fresh seafood (including delicious sushi), burgers, salads, and more complete with a full bar and waterfront views. Oak to Ember is also located by the water with seafood, meat, and seasonal vegetable offerings flavored by their wood-fired grill and 500-gallon smoker.

Across the street, Machaca is a go-to for tacos plus their large selection of tequila, perfect for flights. Inside the Beauport Hotel, 1606 Restaurant & Oyster Bar boasts a full raw bar plus stone-fired pizza, pasta, additional seafood entrees and more, all right off the lobby by Pavilion Beach.

Several favorite Gloucester restaurants are located right downtown, making them the perfect dinner option for a night out after a day exploring the shops. For Italian cuisine that seafood lovers and pasta enthusiasts are sure to love, try Tonno. Further down Main Street, you can’t miss Jalapeño’s, a favorite spot for authentic Mexican cuisine.

Just outside of downtown, Turner’s Seafood Market and Fish ‘n’ Chips Shoppe is a must-visit for ordering delicious fish ‘n’ chips, sandwiches, or chowder, or for picking up fresh seafood to stock your vacation rental. On Washington Street, Captain Vito’s combines a seafood market with dine-in and takeout options like lobster rolls and tacos. And, George’s Restaurant & Bar is a great place for weekly dinner specials and tasty breakfast options. For a last taste of summer, Mile Marker One offers indoor and outdoor waterfront dining with views of Cape Ann Marina.

If local craft brews are on your must-try list, head over to Cape Ann Lanes & Laneside Pub and Brewery. For local beers from around the region, mark your calendar for Blackburn Brewfest on September 13. This annual event features live music and samples of beers, ciders, and meads from 20 breweries, all in support of the Cape Ann Community Foundation.

Our recs for fall treats? Turtle Alley Chocolates is a go-to for turtles, classic chocolates, and seasonal sweets like candy apples, and Holy Cow Ice Cream is a beloved local ice cream spot with an ever-changing flavor selection. And Virgilio’s, in addition to serving local favorite Italian sandwiches, has a case full of cookies, pastries, ad more to pick something up for dessert.

Discover Local Shops

Whether you’re getting ahead on shopping for holiday gifts or just browsing for yourself, Gloucester’s shops are packed with local flavor.

Stop by Mark Adrian Shoes for the perfect fall boots, find coastal-inspired home goods and decor at goodlinens studio, or stock up on seasonal snacks at Common Crow Natural Market. Cape Ann Olive Oil is a must for seasonal flavors (think fig or maple balsamic), and Second Glance Thrift Shop is a great spot for vintage and resale finds.

Stay a While: Accommodations Perfect for Fall

If you’re planning an overnight or weekend getaway, Gloucester has plenty of welcoming spots to rest your head — many with ocean views or walkable downtown access.

Close to downtown, you’ll find the Beauport Hotel (home of 1606 Restaurant and Oyster Bar) and Harborview Inn, both with views of the harbor right by Stacy Boulevard. The Hotel at Cape Ann Marina is also a short ride to downtown with boat access at Cape Ann Marina and Mile Marker One for its on-site restaurant. For places to stay close to some of Gloucester’s best beaches, you’ll want to check out Blue Shutters Beachside Inn and The Vista by Good Harbor Beach, or Cape Ann Motor Inn, located right on Long Beach.

Additional ocean views can be enjoyed from your room at the Atlantis Oceanfront Inn or the Ocean House Hotel at Bass Rocks, and several Rockport locales like The Cove at Rockport, the Emerson Inn, Captain’s Bounty. Also in Rockport is Addison Choate, an upscale boutique hotel just a short walk from the train station and Bearskin Neck.

Need more space? Try the cottages at Sea Lion Motel or book a rental in Gloucester or elsewhere around Cape Ann with Atlantic Vacation Homes.

More to Explore in Gloucester

Fall is also a great time to connect with Gloucester’s local history.

Right on Main Street, you can break from shopping to visit the Sargent House Museum, where visitors can learn about Judith Sargent Murray, an 18th century advocate of education and equality for women, and view artwork by John Singer Sargent and his sister, Emily. The museum is seasonal and open weekends 12-3 PM from Labor Day-Indigenous Peoples’ Day.

Hammond Castle Museum, the home of notable inventor John Hays Hammond Jr. offers the opportunity to explore a medieval-inspired castle plus a rotation of exhibits on history, science, and art. Be sure to check the museum’s event calendar for details on special events this fall like Spiritualism Tours by Candlelight, the Renaissance Faire, and more.

Gloucester is only about 45 minutes to an hour from Boston by car or train— and it’s a perfect add-on if you’re already in Salem for Haunted Happenings this fall. Once you arrive in Gloucester, CATA can help you get around town (and around Cape Ann) with no fares through December 31, 2025.

Whether you’re here for the art, the food, the foliage, or just a quiet moment by the sea, Gloucester has everything you need for a classic New England fall. Check event calendars, make your dinner reservations, and book your stay early — and get ready to fall for Gloucester.