Enjoy the charm of the season in Gloucester with our comprehensive guide. Whether you call Gloucester home or are just visiting, this guide unlocks the best of the season.
Popular events light up the holiday spirit in Gloucester, starting with the enchanting Gloucester's Tree Lighting at Kent Circle & Christmas Parade, a festive gathering that brings the community together to celebrate. With delightful floats and local performers, the event showcases the heart of Gloucester. The Middle Street Walk invites everyone to stroll through beautifully decorated streets, where unique shops and seasonal cheer await. And the Winter Lights on Cape Ann is something you definitely don't want to miss, featuring a dazzling display that captures the magic of Christmas. For more details on these and other fun events and activities, see below!
Happy Holidays!
Top Events Events In and Around Gloucester
- Middle Street Walk
- Gloucester's Tree Lighting at Kent Circle & Christmas Parade
- Winter Lights on Cape Ann
- Deck the Halls at Hammond Castle
- Annisquam Christmas Fair
- Christmas with the Back Bay Ringers (Rockport)
- Cape Ann Makers Holiday Market
🎃 Explore all 7+ featured events below!
Gloucester Events Events
Middle Street Walk (Gloucester) • 0.2 miles
Historic street transformed with holiday cheer and diverse activities.
Gloucester's Tree Lighting at Kent Circle & Christmas Parade (Gloucester) • 0.8 miles
Santa's arrival and a special tree lighting ceremony
Winter Lights on Cape Ann • 1.0 miles
Festive light displays across five coastal communities
Deck the Halls at Hammond Castle (Gloucester) • 2.6 miles
Historic castle transformed into a STEAM museum
Annisquam Christmas Fair (Gloucester) • 2.9 miles
Handmade items crafted by members throughout the year
Christmas with the Back Bay Ringers (Rockport) • 3.8 miles
Acclaimed handbell ensemble performing holiday classics.
Cape Ann Makers Holiday Market • 4.3 miles
Showcasing local artisans and crafters
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