Holiday Events in Gloucester, Massachusetts 

December 01, 2023 / Food and Drink, Good to Know, Outdoor Adventures, Things to Do & See

Are you ready to celebrate the season with some festive music, delicious meals, and some unique shopping options? Gloucester has so many events, activities and dining options that you won’t want to miss a thing this holiday season. 

From picturesque snowy beaches to festively decorated downtown streets, Gloucester has something for everyone this time of year. Join us and find your spirit of the season at one of the many events listed below. 

4th Annual Winter Lights on Cape Ann

Discover Gloucester & The Greater Cape Ann Chamber of Commerce are thrilled to bring you the 4th Annual Winter Lights on Cape Ann, running from Small Business Saturday through New Year’s Day across Greater Cape Ann: Gloucester, Rockport, Essex, Ipswich and Manchester-by-the-Sea. Businesses from each community will be illuminating their storefronts with festive lights and decor, making it a beautiful driving route, and encouraging visits to each of the five downtowns. Some businesses are taking part in the decorating contest again this year, so keep an eye out for opportunities to vote for your favorites! All who cast a ballot will be entered to win a $50 Greater Cape Ann Gift Check in the new year. Find the lineup at

Photo courtesy of the Kent Circle Tree Lighting

Gloucester’s Tree Lighting at Kent Circle & Christmas Parade

Gloucester’s Tree has been brought down from Nova Scotia for another festival Kent Circle Tree Lighting & Christmas Parade happening Sunday, November 26th! Hosted by the Christmas Parade Committee, this annual parade kicks off at the State Fish Pier at 3:00 pm and fills downtown Gloucester with holiday cheer en route to the parade end and tree lighting at Kent Circle. 

Annisquam Christmas Fair 

Also being held on December 2, 2023, members of the Annisquam Sewing Circle are hosting a Christmas Fair. 

The fair is being held from 8 am to noon, December 2, 2023, at the Village Hall, 34 Leonard Street in Gloucester. Some of the crafts and goods you will find include wreaths, table and mantle pieces, cards, needlepoint ornaments and so much more. 

The proceeds from this Annisquam Sewing Circle event are donated to Cape Ann nonprofits and as scholarships to Gloucester High School graduating seniors who are going on to further study.

2nd Annual Gloucester Fishtown Horribles Parade of Trees 

Don’t miss out on this family-friendly and free tradition in Gloucester. The 2nd Annual Gloucester Fishtown Horribles Parade of Trees encourages visitors to take a stroll to enjoy the decorations on beautifully adorned trees. 

Being held on December 3, 2023, at the First Baptist Church on Gloucester Avenue, this event promises to put you in a festive mood. Enjoy the twinkle of these trees decorated by local groups and organizations and take a chance to win one in the raffle. 

Happy Half Merry-thon Run 

Sunday, December 3, 2023, join a festive and fun-loving running crew as they enjoy beautiful ocean views along the scenic coastline in Gloucester and Rockport! Take part in the Happy Half Merry-thon Run by lacing up your sneakers for the half-marathon, 5K or run both back-to-back! The 5K starts at 9 am and the half-marathon at 10 am on beautiful Good Harbor Beach, Thatcher Road in Gloucester. Register on their site

Ladies Night Downtown Gloucester 

Grab your shopping list and your best girlfriends and head to Gloucester on December 7, 2023. Enjoy the 50th Annual Ladies Night Downtown Gloucester from 10 am to 10 pm as you get some shopping done, enjoy holiday music, view the Lobster Trap Tree and taste some of the best cuisine on the North Shore. 

Lobster Trap Tree Lighting on Harbor Loop

Did you know…?

Gloucester’s famous Lobster Trap Tree is going to be at Captain Solomon Jacobs Park on the Harbor Loop this year!

Supported by Art Haven, volunteers, and sponsors, the Lobster Trap Tree is a beautifully illuminated tree-shaped structure consisting of lobster traps donated by local fishermen and suppliers. Hung along the traps are buoys artistically decorated by children from the community. The Lobster Trap Tree, along with the Lobster Trap Menorah at Temple Ahavat Achim each year, and coming back for its second year: Cape Ann Museum’s Lobster Trap Lighthouse, are symbols of Gloucester’s active working waterfront, authenticity, and community togetherness during the holiday season. The Lobster Trap Tree Lighting is scheduled for Saturday, December 9th at 4:30 pm. Find buoy decorating workshops for your little one at

Deck the Docks 

Sponsored by Maritime Gloucester, Deck the Docks is being held on Saturday, December 9, 2023 at 23 Harbor Loop. From 10 am to 6 pm, enjoy the museum, crafts for kids, storytime, Art Haven art, and cocoa and cookies before the pier lighting at 6 pm. Check out the full schedule on the Maritime Gloucester site. 

A Heavenly Baroque Christmas with Gloucester Meetinghouse Foundation & Gloucester 400+

Love music? Don’t miss Gloucester Meetinghouse Foundation’s A Heavenly Baroque Christmas: Celestial Works From Spain and New Spain happening on the 7th at 7:30 pm in collaboration with Gloucester 400+. The Meetinghouse is located at 10 Church Street in Gloucester. 

Middle Street Walk 

This time-honored event is one you won’t want to miss. Free events are scheduled all day along Middle Street and beyond including bell ringers, wreaths and greenery sales, trolley rides, live music and concerts, baked goods, Gingerbread Houses, sing-a-longs, performances and so much more! 


The Middle Street Walk Committee has planned quite the walk for the 25th year and hopes to see you there. The events start at 10 am on December 9th and run until the Lobster Trap Tree Lighting at 4:30 pm. 

Men’s Night Downtown Gloucester 

Being held this year on December 14th, Gloucester’s 47th Annual Men’s Night is similar in the festivities to the Ladies’ Night, except this time the treats and specials are geared toward the men doing the shopping.


Gloucester offers so much to do every holiday season from joining friends for a scrumptious dinner to enjoying all the festivities leading up to Christmas. There truly is something for everyone in Gloucester during the holidays.