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Gloucester, Massachusetts
Your coastal escape, just 45 minutes from Boston.
Plan the perfect trip, any time of the year.
No matter when you visit, Gloucester offers something special in every season. From sun-soaked beach days to cozy coastal escapes, let this guide help you plan your ideal getaway year-round.
The 2025-2026 Discover Gloucester Visitor Guide is now available in print and digitally!
Featured Business: 1606 Restaurant
Discover Gloucester Spotlight
Located in the Beauport Hotel Gloucester, the 1606 Restaurant & Oyster Bar offers modern American cuisine prepared with local ingredients. Open year-round, guests and visitors can dine in elegance in the main dining room, sit back and unwind at the bar, or cozy up on the deck around the firepit with a delicious seasonal dish, appetizer, or signature cocktail while taking in the oceanfront views.
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Fall is the perfect time for a coastal getaway, and The Vista offers easy access to Good Harbor Beach, downtown Gloucester’s shops and restaurants, and all the charm of Cape Ann. Plus, if your autumn adventures include a trip to Salem, it’s just a short drive or train ride away. 🍂
#VisitNorthOfBoston #VisitMA #GloucesterMA #CapeAnn #NewEngland #Fall #FallTravel #SalemMA #Salem
Weekend mornings are better by the water. Enjoy breakfast at Mile Marker One every Saturday and Sunday! ☀️🍴
#GloucesterMA #VisitNorthofBoston #CapeAnn #MileMarkerOne #Breakfast #NewEngland
Come explore the newly reopened Sawyer Free Library with us 📚 — a beautiful blend of Gloucester’s history and modern design. From cozy corners filled with new reads to the light-filled reading lounge overlooking City Hall, every space invites you to slow down and stay awhile.
Learn more about the library and upcoming events at sawyerfreelibrary.org.
#sawyerfreelibrary #gloucesterma #capeann #library #supportlocal
Fall vibes on tap 🍁 Harbor 9 Golf & Sports Bar is serving up Pumpkinhead Ale, Spiked Cider, and the must-try Pumpkin Espresso Martini.
This fall, don’t miss Gloucester’s go-to spot for golf simulators, great drinks, and good times. ⛳️
#GloucesterMA #CapeAnn #Harbor9Golf #PumpkinSpice #Fall #NewEngland #VisitMA
🍂There`s still time to get out on the water this fall in #GloucesterMA! ⛵️
Start planning your next day on the water with:
@capeanncruises - Scenic Gloucester Harbor Tours and Sunset Cruises run through October! Book at CapeAnnCruises.com. (Photo credit: Cape Ann Cruises.)
@artemis_sails - Artemis has a heated on-deck pilot house with 360-degree views and a climate-controlled cabin. Visit ArtemisSails.com to learn more about sailing this fall.
@schoonerlannon_ Sailing select dates through mid-October. Don`t miss the ghost stories sail with @hauntedharborwalk on Oct. 15! Book at Schooner.org.
@capeannwhalewatch - Trips run through November 2. Book at SeetheWhales.com. (Photo Credit: Tina McMahon-Foley, head naturalist at Cape Ann Whale Watch.)
@7seaswhalewatch - Trips run through October 26. Book at 7SeasWhaleWatch.com. (Photo credit: 7 Seas Whale Watch.)
#DiscoverGloucester #CapeAnn #OntheWater #NewEngland #NewEnglandFall #VisitNorthofBoston
From Cape Ann Plein Air to candlelight tours at Hammond Castle Museum, Haunted Harborwalk tours, and more—Gloucester is packed with fall fun this October! 🍂 Head to discovergloucester.com to see the full calendar.
#DiscoverGloucester #VisitNorthofBoston #GloucesterMA #NewEngland #October #CapeAnn
This is your reminder to take a stroll down Stacy Boulevard to see the beautiful dahlias planted by Generous Gardeners! 🏵️ 🌼
Generous Gardeners will hold their annual, sell-out cut dahlia sale starting at 10 AM on Saturday, October 4th (October 11t rain date) near the tennis courts on Stacy Blvd. Blossoms will be fresh cut and arranged into beautiful bouquets. The sale ends at noon or when they sell out, so be sure to stop by early!
#DiscoverGloucester #GloucesterMA #VisitNorthofBoston #CapeAnn #NewEngland #Gardens #Dahlias
There’s still time to get out on the water with 7 Seas Whale Watch! 🐋🍂
Trips run through October 26, and fall is one of the best seasons to spot whales off Gloucester’s coast. Reserve your spot at 7seaswhalewatch.com
or through the link in our bio.
📸: 7 Seas Whale Watch
#GloucesterMA #NewEngland #WhaleWatching #VisitNorthofBoston #VisitMA
🎨 Wander through Rocky Neck Art Colony while in #GloucesterMA and see why generations of artists have made this seaside destination their home.
Visit RockyNeckArtColony.org or the link in our bio to find upcoming events and exhibitions, gallery hours, and more.
#DiscoverGloucester #CapeAnn #RockyNeckArtColony #RockyNeck #VisitNorthofBoston #VisitMA #LocalArt
Fall may be upon us, but there`s still time to dine outside by the water here in #GloucesterMA!
Swipe for a peek at 51 Rocky Neck and view the full menu or book your table at the link in our bio / 51RockyNeck.com
#VisitNorthofBoston #CapeAnn #VisitMA #RockyNeck #NewEngland
🦞 It’s National Lobster Day, and where better to celebrate than #GloucesterMA? From rolls to lobster smash burgers, there’s no wrong way to enjoy lobster in America’s Oldest Seaport.
📍 @bluecollarlobsterco / 📸: @tasteofmassachusetts
📍 @milemarkerone
📍 @minglewoodharborside / 📸: @magba__
📍 @1606restaurantandoysterbar
📍 Captain Vito`s
📍 @seaport_grille
📍 @51rockyneck / 📸: @tasteofmassachusetts
#DiscoverGloucester #VisitMA #VisitNorthofBoston #Lobster #LobsterRolls #CapeAnn #NewEngland
Discover your fall look at Second Glance Thrift Store 🍂🧥 From cozy layers to unique finds, it’s a go-to spot for autumn fashion in Gloucester. And, every purchase supports The Open Door, helping to nourish and strengthen the community. 💙
#GloucesterMA #CapeAnn #Thrifting #Fall #NewEngland #VisitMA #supportlocal
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