Winter in Gloucester, MA: Cozy Coastal Escapes in February
January 23, 2026 / Things to Do & SeeThere’s something special about visiting Gloucester, Massachusetts in February. While summer gets all the sun-soaked attention, winter here has its own soft, salty feel with foggy mornings hugging the harbor, the sound of waves whispering against ice-flecked pilings, and cozy long afternoons warming up over comfort food and sea views. If you’re craving a winter… Read more »
Read MoreCozy Up to the Coast: Winter in America’s Oldest Seaport
December 17, 2025 / Things to Do & SeeWinter in Gloucester, Massachusetts, is a season of peaceful beauty, cozy moments, and genuine New England charm. With fewer crowds and abundant local experiences, the colder months offer a chance to slow down, explore at your own pace, and uncover the treasures of America’s Oldest Seaport and its neighboring Cape Ann communities. From outdoor adventures… Read more »
Read MoreDecember in Gloucester, MA: Holiday Fun & Cozy Winter Activities
November 25, 2025 / Things to Do & SeeIn December, Gloucester, Massachusetts glows with a special kind of coastal magic. Imagine historic streets lit by twinkling lights, the salty ocean air mingling with the scent of evergreen, and rich traditions that feel both historic and heartwarming. Whether you’re planning a winter escape, or a local’s staycation, here’s how to really experience the holiday… Read more »
Read MoreShop Local This Small Business Saturday in Gloucester, MA
November 05, 2025 / Things to Do & SeeSmall Business Saturday is just around the corner, and there’s no better place to celebrate than right here in Gloucester, Massachusetts. On Saturday, November 29, join us in supporting the independent shops, restaurants, and artists that give our coastal community its charm. Founded in 2010, Small Business Saturday is a national movement encouraging people to… Read more »
Read MoreYour Guide to Fall Shopping in Gloucester, MA
August 20, 2025 / Things to Do & SeeGloucester is the perfect destination for a fall getaway — and there’s no better time to refresh your wardrobe, update your home, and stock up on seasonal flavors from local shops. Whether you’re looking for cozy layers, autumn-inspired homegoods, or ingredients for your favorite fall recipes, Gloucester offers a variety of shopping spots that blend… Read more »
Read MorePlan a Fall Trip to Gloucester, MA: Things to Do, See & Eat by the Coast
August 18, 2025 / Good to Know, Things to Do & SeeLocated 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… Read more »
Read MoreCan’t-Miss Events at This Year’s Gloucester Schooner Festival
July 29, 2025 / A Local Favorite, History/Maritime, Things to Do & SeeEvery Labor Day weekend, Gloucester, Massachusetts transforms into a bustling celebration of maritime history, community spirit, and—of course—majestic schooners. Now in its 41st year, the Gloucester Schooner Festival returns from Wednesday, August 27 to Sunday, August 31, 2025, bringing with it a full slate of family-friendly events, sailing opportunities, and more. Whether you’re a seasoned… Read more »
Read MoreShop Local in Gloucester, MA This Tax-Free Weekend!
July 24, 2025 / Things to Do & SeeGet ready for a shopping getaway in Gloucester, MA— Tax‑free weekend is back on August 9–10! It’s the perfect chance to explore charming storefronts, score savings, and enjoy seaside breezes, all without paying sales tax on most* items. From luxury fashion and home goods to artisanal finds, here’s your guide to where to go and what… Read more »
Read MoreUnforgettable Gloucester: 15 Places Every Visitor Should Explore
April 30, 2025 / Good to Know, Things to Do & SeeFrom historic homes and scenic lighthouses to world-class museums and a seaside art colony, Gloucester is full of places that celebrate its rich past and creative spirit. Whether you’re drawn to coastal views, cultural attractions, or local history, there’s something here for every kind of explorer. Here’s a roundup of must-visit spots around the city…. Read more »
Read MoreExperience Winter by the Sea During Gloucester’s So Salty
January 09, 2025 / A Local Favorite, Things to Do & SeeWinter in Gloucester comes alive with the 5th Annual Gloucester’s So Salty festival! Free and open to the public, this beloved event runs January 24-25, celebrating the city’s unique blend of maritime heritage, creative spirit, and unmistakably salty character. Whether you’re a local looking to shake off the winter blues or a visitor seeking a… Read more »
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