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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: Hammond Castle Museum
Discover Gloucester Spotlight
Hammond Castle Museum was the home and laboratory of John Hays Hammond Jr. and now serves as a museum, cultural arts center and venue welcoming guests daily throughout the season.
Learn More
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
Cape Ann Plein Air returns October 4–12, bringing incredible artists to Gloucester, Rockport, Essex, and Manchester-by-the-Sea to paint Cape Ann’s beauty in the open air.
Find the full event lineup at capeannpleinair.org or the link in our bio.
🎨: Kirk Larsen
📸: Cape Ann Plein Air Staff
#CapeAnnPleinAir #PleinAir #LocalArt #GloucesterMA #CapeAnn #VisitNorthofBoston #VisitMA #NewEngland
Step inside history at Hammond Castle Museum this fall! 🏰
Hammond Castle Museum has a packed lineup of special events this fall— from Spiritualism Tours by Candlelight on Thursdays through October, to Trick or Treat at the Castle on October 30, and Renaissance Faire Day on November 8. Plan your visit and see the full lineup at hammondcastle.org or through the link in our bio.
📸: @theprettypostcard
#HammondCastle #GloucesterMA #CapeAnn #VisitNorthofBoston #VisitMA #NewEngland
Fall is one of the best times to spot whales at Stellwagen Bank, just 12 miles off Gloucester’s coast!🐋🍂
Cape Ann Whale Watch runs daily trips through November 2—don’t miss your chance to experience these incredible animals up close. Learn more and grab your tickets at seethewhales.com or through the link in our bio!
📸: Tina McMahon-Foley, head naturalist at Cape Ann Whale Watch
#GloucesterMA #CapeAnn #WhaleWatching #NewEngland #VisitNorthofBoston #VisitMA
Kick off the weekend with tacos and tequila at Machaca! 🌮🍹
Machaca brings the flavors of Mexico City to downtown Gloucester with street tacos, margaritas, and one of the North Shore’s largest selections of tequila and mezcal.
#DiscoverGloucester #GloucesterMA #NewEngland #Tacos #CapeAnn
Fall is right around the corner, but schooners are still sailing here in #GloucesterMA!
⛵ Join Schooner Lannon for a sail through early October, and help raise the sails, take in breathtaking views of the harbor, or just kick back on the water to cap off the summer on Cape Ann.
Book your sail at schooner.org.
#DiscoverGloucester #VisitNorthofBoston #CapeAnn #NewEngland #SchoonerLannon #OntheWater #sailing
Fall getaway, anyone? 🍂 Sea Lion Motel & Cottages is just minutes from downtown Gloucester and 1 mile from Good Harbor Beach — the perfect home base for exploring, then cozying up in your own cottage after a day out in America’s oldest seaport.
#DiscoverGloucester #VisitMA #VisitNorthOfBoston #GloucesterMA #FallGetaway
Not all of Gloucester’s ghosts are resting…
Step into the shadows on a 90-minute Haunted Harborwalk tour this fall. On Gloucester’s new original ghost tour, you’ll stroll along the harbor and through downtown while hearing chilling tales of sea serpents, spectral sailors, the witches of Dogtown, and more.
🕯️ Book your tour now:
haunted-harborwalk-gloucester.squarespace.com
#GloucesterMA #NewEngland #NewEnglandFall #GhostTour #CapeAnn #VisitNorthofBoston
What a weekend on the water! ⛵ Gloucester Schooner Festival is an annual Labor Day weekend tradition, so mark your calendars to join us next year.
Want to get out on the water sooner? Schooner sails, whale watches, and harbor cruises are still running in September (and some through October!) Find ways to get on the water this month at discovergloucester.com or the link in our bio.
#GloucesterMA #Schooner #NewEngland #CapeAnn #OnTheWater #VisitNorthofBoston #Sailing
Explore Gloucester this month with walking tours, schooner sails, Blackburn Brewfest, and unique events like Stand Up for Art and Science, celebrating creativity and discovery!
🌊⚓ Check out our full event calendar at the link in bio or discovergloucester.com.
P.S. Whale watches run through most of October! Be sure to add an excursion with @7seaswhalewatch or @capeannwhalewatch to your fall trip to Gloucester! 🍂🐳
📸: Tina McMahon, @capeannwhalewatch
#GloucesterMA #CapeAnn #NewEngland #VisitNorthofBoston #VisitMA #ThingstoDo
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