December in Gloucester, MA: Holiday Fun & Cozy Winter Activities

November 25, 2025 / Things to Do & See

In 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 spirit in Gloucester.

Deck the Halls at Hammond Castle Museum

At Hammond Castle Museum, “Deck the Halls” transforms the iconic stone halls into a candlelit wonderland. From November into early January, the rooms are draped in lush garlands, white birch, and lights, with holiday decor around every corner. On Thursday evenings in December, you can even join a Candlelight Tour and wind through the Great Hall and hidden nooks by lantern glow.

While at the museum, be sure to check out the Hammond in Italy temporary exhibition, which showcases John Hays Hammond Jr.’s interest in Italian art and architecture through his travels in Italy.

Reservations are encouraged for Deck the Halls and can be made at hammondcastle.org.

Festive Gatherings

At the Beauport Hotel, the annual Holiday Open House is a beloved tradition. This year’s open house takes place on December 2, and guests can stroll the hotel’s historic rooms, enjoy live jazz, sweet treats. The hotel is also running a toy drive that you can support by bringing an unwrapped gift.

The hotel’s Jingle Bar also returns on select December 3, 10, 17, and 22, offering the opportunity mingle by the fireplace with champagne, seasonal cocktails, and live music in the oceanfront ballroom.

Gloucester’s Iconic Lights & Sights

One of Gloucester’s most charming holiday traditions? The Lobster Trap Tree! Local lobstermen donate traps, volunteers stack them into a towering tree, with painted buoys by Cape Ann Art Haven and lights completing the look. This year’s lighting is set for December 13 at 4:30 pm at Solomon Jacobs Landing.

This year’s Lobster Trap Menorah Lighting is set for December 16 at 6:00 pm at Temple Ahavat Achim. This annual Chanukah celebration includes songs and sweet treats outside, then moves indoors for a concert with the renowned Ezekiel’s Wheels Klezmer Band. Events are free, with registration required to attend the concert.

Strolling & Shopping

• The Middle Street Walk on December 13 is a winter tradition: Enjoy live music, stop into shops and galleries, and enjoy seasonal festivities and holiday cheer all along one of Gloucester’s loveliest streets.

• Art lovers will want to plan for the Rocky Neck Holiday Art Trek on December 13, where local galleries, studios, and shops open their doors for a festive seasonal showcase.

• For more local shopping, Gloucester holds Ladies’ Day and Men’s Day downtown each December. Both days are the perfect excuses for holiday shopping, drinks, and community merriment. Ladies’ Day takes place annually on the first Thursday in December, and Men’s Day is on the second Thursday.

Cozy Winter Dining & Seasonal Stays

• Igloos at Mile Marker One: For a truly magical winter dinner, dine in a heated waterfront igloo at Mile Marker One (at the Hotel at Cape Ann Marina). Nothing says cozy like a glass of wine by the water as snow drifts outside.

• Restaurant Week at Minglewood Harborside: Serenitee Restaurant Group is offering a special Restaurant Week menu at Minglewood Harborside, December 1-15. Dine-in for a special pre-fixe menu, plus featured cocktails and $1.25 oysters.

Looking to stay in Gloucester this month? Several hotels are open year-round and are perfect for winter stays. In addition to the Hotel at Cape Ann Marina and the Beauport Hotel, be sure to check out Cape Ann Motor Inn on Long Beach and Harborview Inn right by the Fishermen’s Memorial statue.

Featured image credit: Melissa Cox