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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: Beauport Cruiselines
Discover Gloucester Spotlight
Cruise historic Gloucester harbor in style! Beauport Cruiselines is the perfect venue for your celebration, corporate meeting or wedding rehearsal dinner.
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Winter in Gloucester just got sweeter with seasonal hot cocoa specials at Cape Ann Lanes! ☕️❄️
Cozy up to a fire pit in their winter beer garden, or stop by the bar to grab one after candlepin bowling this month.
We tried the Salted Caramel with caramel syrup, whipped cream, and chocolate sauce and sprinkles, and the Snow Day Sprinkle with whipped cream, vanilla snowman marshmallows, and sprinkles. ☃️
#GloucesterMA #winter #NewEngland #capeannlanes #hotcocoa
@commoncrowglo has everything you need for cozy winter meals here in Gloucester, MA!
Pick up prepared foods like their special lasagna, or cozy up with something sweet like seasonal cheesecakes or hot cocoa.
Don’t forget to pick up some tea to get through these chilly winter days! 🍵
#shopsmall #supportlocal #GloucesterMA #newengland #winter
Save the date! Gloucester`s So Salty takes place January 24-25, 2026! ❄️
This two-day festival features ice sculptures, live music, salty treats, and engaging cultural activities scattered throughout Downtown Gloucester.
Plan your visit at capeannmuseum.org, or check out our latest blog post on discovergloucester.com / the link in our bio.
📸: Aram Boghosian
#GloucesterMA #NewEngland #CapeAnn #NewEnglandWinter #January
Escape to Gloucester this winter and enjoy breathtaking views and cozy adventures.
Read our latest blog post to start planning your trip today: discovergloucester.com or click the link in our bio.
📸:
Igloo dining at @milemarkerone
Live music at @thecutlive
@harbor9golf indoor golf & sports bar
Pizza and bowling at @capeannlanes, photo by @theprettypostcard
Snowy owl during winter birdwatching
#GloucesterMA #NewEngland #Winter #CapeAnn #WinterTravel
Still searching for the perfect gift on Cape Ann? 🎁
Add in a quick trip to Rockport while shopping for the holidays in #GloucesterMA. From local art at Rockport Art Association and Coastal Locals to tickets for your next night out with Rockport Music, or something cozy and comfortable from Denim Blanket Company, there are some great last-minute gifts to be found on Cape Ann.
Visit discovergloucester.com for more local shopping ideas in Gloucester and Rockport, and you’re sure to find something for everyone on your list.
#CapeAnn #RockportMA #SupportLocal
Stop by @denimblanketco in Rockport to pick up thoughtful, American-made gifts with a coastal feel. This shop blends classic New England style with modern craftsmanship, offering American-made blankets, apparel, and gifts that feel as good as they look.
Learn more about this local favorite on the blog at discovergloucester.com.
#RockportMA #CapeAnn #NewEngland #ShopSmall #SupportLocal
Turner`s Seafood has so many great additions to your holiday table this season!
From fresh, locally caught seafood, to chowders and bisques, prepared foods, and more, you can view all the options and place your order at turners-seafood.com.
#GloucesterMA #Holidays #VisitNorthofBoston #CapeAnn #NewEngland
Last-minute holiday shopping is the best when you shop local. Find something for everyone on your list this weekend in #GloucesterMA! 🎁❄️
Stroll down Main Street to shop shoes, olive oil, books, home goods, art, clothing and accessories, and so much more.
And don’t forget to explore beyond downtown with shops like Second Glance Thrift Store, the galleries in Rocky Neck Art Colony, or by picking up a gift card for a favorite restaurant or activity in town.
#newengland #capeann #supportlocal #holidays
Celebrate the holiday season at Deck the Halls at Hammond Castle Museum 🎄✨
This festive holiday experience runs through January 4, transforming the castle with elegant décor inspired by medieval and Renaissance Europe. While you’re there, we also recommend visiting the Hammond in Italy exhibit, on view through January 4 as well. Tickets may be reserved at hammondcastle.org.
#HammondCastle #GloucesterMA #CapeAnn #NewEngland #Holidays
❄️ Winter in Gloucester ❄️
Explore America’s oldest seaport this winter and experience cozy dining, local shopping, and festive sights around town.
Plan your visit at discovergloucester.com/winter
#GloucesterMA #NewEngland #Holidays #NewEnglandWinter #CapeAnn
goodlinens studio is a go-to holiday shopping destination right on Main Street in #GloucesterMA!
From linen towels to cozy winter socks, accessories, home decor, and so much more, this is one local shop where you`re sure to find something for everyone on your list.
#goodlinens #NewEngland #CapeAnn #ShopSmall
Celebrate the holidays this weekend in Gloucester, MA! ☃️
Swipe for a peek at this weekend`s events, and check the calendar on discovergloucester.com for the full lineup.🎄 ❄️
#GloucesterMA #Holidays #NewEngland #CapeAnn #Winter
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