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.
Beauport Hotel Winter Offer
Stay at Beauport Hotel with rates starting at just $199 on weekdays from January 3-March 31, 2025.
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
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.
