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!
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Top Holiday Events In and Around Gloucester
- Gloucester’s Tree Lighting at Kent Circle & Christmas Parade
- Middle Street Walk
- Winter Lights on Cape Ann
- Annisquam Christmas Fair
- A Heavenly Baroque Christmas
- Cape Ann Makers Holiday Market
See these and even more events listed below!
Gloucester Holiday Light Displays
Winter Lights on Cape Ann
What to Expect:
Over 100 lighted locations in five coastal communities.
Description:
Winter Lights on Cape Ann is a spectacular display of lighted locations throughout Gloucester, Essex, Ipswich, Manchester-by-the-Sea, and Rockport. Local businesses decorate their storefronts with twinkling lights and creative window displays, creating a joyful atmosphere for visitors.
Where: Gloucester | More Info: Winter Lights on Cape Ann
Gloucester Holiday Markets and Shopping
Annisquam Christmas Fair
What to Expect:
Handcrafted gifts and local foods in a festive community setting.
Description:
The Annisquam Christmas Fair features handcrafted items, local foods, and beautiful decorations, showcasing the community's spirit and creativity.
Where: Gloucester | More Info: Annisquam Christmas Fair
Cape Ann Makers Holiday Market
What to Expect:
Semi-juried vendor market featuring local hand crafts.
Description:
Cape Ann Makers Holiday Market showcases high-quality, handmade crafts from local makers in Gloucester, Essex, Manchester-by-the-Sea, and Rockport. The event celebrates local artisans and provides a unique shopping experience with original designs and upcycled materials.
Where: Gloucester | More Info: Cape Ann Makers Holiday Market
Gloucester Holiday Shows and Entertainment
A Heavenly Baroque Christmas
What to Expect:
Candlelit concert with classical music from Spain and New Spain.
Description:
The Musicians of the Old Post Road present a candlelit concert featuring celestial works from Spain and New Spain, including music by Iribarren, Salazar, and Zumaya, the first Mexican classical composer of indigenous descent. The event is joined by Ensemble La Fontegara and distinguished soloists Adriana Ruiz and Hilary Anne Walker.
Where: Gloucester | More Info: A Heavenly Baroque Christmas
Gloucester Other Holiday Activities
Gloucester’s Tree Lighting at Kent Circle & Christmas Parade
What to Expect:
Santa's arrival by parade and tree lighting ceremony.
Description:
Join Gloucester for its annual Christmas Parade and Tree Lighting at Kent Circle. The parade starts at the State Fish Pier and winds through downtown Gloucester, culminating in a festive tree lighting ceremony. Children can meet Santa and enjoy free popcorn and cocoa while signing holiday cards for troops overseas.
Where: Gloucester | More Info: Gloucester’s Tree Lighting at Kent Circle & Christmas Parade
Middle Street Walk
What to Expect:
Horse-drawn hay ride and gingerbread creation contest.
Description:
The Middle Street Walk is a festive event in Gloucester's Historic District, featuring a variety of activities including a horse-drawn hay ride, dancing performances, and a gingerbread creation contest. The event showcases local organizations and historic sites, offering a unique blend of community spirit and holiday cheer.
Where: Gloucester | More Info: Middle Street Walk
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Beverly Cove (11 miles)
- Beverly (12 miles)
- Salem (14 miles)
- Danvers (14 miles)
- Peabody (15 miles)
- South Peabody (16 miles)
- Saugus (20 miles)
- Wakefield (22 miles)
- Revere (23 miles)
- Reading (23 miles)
- Melrose (23 miles)
- Haverhill (24 miles)
- Stoneham (24 miles)
- Chelsea (24 miles)
- Malden (24 miles)
- Everett (24 miles)
- North Andover (25 miles)
- Medford (26 miles)
- Wilmington (26 miles)
- Woburn (27 miles)
- Winchester (27 miles)
- Boston (27 miles)
- Somerville (27 miles)
- South Boston (28 miles)
- Methuen (28 miles)
- Cambridge (28 miles)
- Burlington (28 miles)
- Arlington (29 miles)
- Tewksbury (29 miles)
- Salem (30 miles)
- Belmont (30 miles)
- Quincy (30 miles)
- Brookline (30 miles)
- Weymouth (31 miles)
- Lexington (31 miles)
- Billerica (31 miles)
- Watertown (31 miles)
- Jamaica Plain (31 miles)
- Portsmouth (32 miles)
- Milton (33 miles)
- Dracut (33 miles)
- Braintree (33 miles)
- Lowell (33 miles)
- Waltham (33 miles)
- Newton (34 miles)
- Chelmsford (36 miles)
- Dedham (36 miles)
- Randolph (37 miles)
- Needham (37 miles)
- Derry Village (38 miles)
- Derry (38 miles)
- Wellesley (39 miles)
- Westford (39 miles)
- Norwood (40 miles)
- Canton (40 miles)
- Acton (40 miles)
- Stoughton (41 miles)
- Brockton (41 miles)
- Dover (42 miles)
- Natick (42 miles)
- Nashua (42 miles)
- Framingham (45 miles)