Winter in Gloucester, MA
Winter in Gloucester brings coastal charm, cozy dining, unique shopping and outdoor strolls, and more. Wander through downtown, set out for some birdwatching, or take in the picturesque winter views from walking trails or beaches. With local shopping, seasonal events, and cozy coastal vibes, Gloucester is the perfect place to embrace the warmth and wonder of winter by the sea.
December in Gloucester, MA: Holiday Fun & Cozy Winter Activities
In December, Gloucester, Massachusetts glows with a special kind of coastal magic.
Off-Season Dog-Friendly Beaches
Find options to explore local beaches with your furry friend during the off-season months.
5 Things to do in the Winter
Here are just five ideas to inspire your next wintery visit to Gloucester and Cape Ann.
Winter Events
Cupid's Cabaret
February 13, 2026
Celebrate Valentine’s Day early this year at Gloucester Stage with…
Folly Cove Designer-Inspired Valentine’s Day Card-Making
February 14, 2026
Drop into the Teen Room at the Sawyer Free Library…
Kids' Free Week: Self-Guided Tours
February 16, 2026
Discover, Explore, and Learn at Hammond Castle Museum this February…
Kids' Free Week: Self-Guided Tours
February 17, 2026
Discover, Explore, and Learn at Hammond Castle Museum this February…
Kids' Free Week: Self-Guided Tours
February 18, 2026
Discover, Explore, and Learn at Hammond Castle Museum this February…
KPop Huntrix Concert Experience and Meet & Greet
February 18, 2026
Join us for a one-of-a-kind KPop Demon Hunters-themed musical experience.…
Kids' Free Week: Self-Guided Tours
February 19, 2026
Discover, Explore, and Learn at Hammond Castle Museum this February…
Kids' Free Week: Self-Guided Tours
February 20, 2026
Discover, Explore, and Learn at Hammond Castle Museum this February…
The History of Medieval Arms & Armor and Self-Guided Tours
February 20, 2026
10:30 am - 11:30 am: Presentation followed by the opportunity…
Bridgerton Afternoon Tea at the Castle
February 28, 2026
Please note: As one of our major fundraisers of the…
Bridgerton Ball at the Castle
February 28, 2026
Please note: As one of our major fundraisers of the…
This Season’s Must-Do’s:
Igloo Dining at Mile Marker One
Don’t miss Mile Marker One’s new Igloo Dining Experience! A unique new concept that promises to elevate dining and celebrations in a way that blends innovation, nature, and luxury on the water at Cape Ann Marina. Experience Gloucester’s enchanting atmosphere with family and friends with a curated selection of food and beverages in a one-of-a-kind igloo dining dome under the stars. New winter menus start Dec. 14 and Sunday brunch begins Dec. 17!
Photo credit: Matthew Sheehan
Winter Birdwatching on Cape Ann
Cape Ann, renowned for its stunning coastline and charming towns, isn’t just a haven for summer vacationers. In fact, it holds a well-kept secret for bird enthusiasts: its exceptional winter birdwatching experiences.
Plan Your Visit
Plan your perfect winter getaway and find seasonable things to do in Gloucester with our guide to the best places to shop, stay, dine, and explore this season!
Shop
Shop for unique holiday gifts at Gloucester’s local stores, where you’ll find handcrafted treasures and coastal-inspired items, perfect for the season.
Stay
Stay in one of Gloucester’s charming inns, hotels, or B&Bs, offering cozy accommodations by the sea or in the heart of downtown.
Dine
Dine at Gloucester’s local restaurants, serving fresh seafood and seasonal dishes to warm you up after a day of exploring.
Things to Do
From festive events to winter adventures, there’s plenty to experience during your visit to Gloucester.
Funded, in part, by the Massachusetts Office of Travel and Tourism.
