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.

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!

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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.

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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!