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Gloucester
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Popular Events in Gloucester, MA
Dec
11
John Cafferty and The Beaver Brown Band
Dec 11, 2026 03:00 PM
The Cut Live
Dec
5
4th Annual Operation Keep Gloucester Warm
Dec 05, 2026 05:00 AM - 09:00 AM
Trinity Congregational Church
Dec
12
15th Annual Spruce Road Extravaganza
Dec 12, 2026 06:00 PM - 10:45 PM
Blue Collar Lobster Company
100.00 USD
Dec
13
Once Upon a Winter: Tales of Wonder Through a Child's Eyes
Dec 13, 2026 11:00 AM
Gloucester Unitarian Universalist Church
Dec
12
Middle Street Walking Tour
Dec 12, 2026 06:00 AM - 09:00 AM
27 Pleasant St
Dec
6
Happy Holidays Half MerryThon & 5K
Dec 06, 2026 04:00 AM
Good Harbor Beach
Dec
9
Beauport Hotel's Mistletoe Lounge: Jingle Bells & Cowboy Boots
Dec 09, 2026 01:00 PM - 04:00 PM
Beauport Hotel Gloucester
USD 18 to 162
Dec
5
Special Jewelry Event! Diva Donna
Dec 05, 2026 06:00 AM - Dec 06, 2026 01:00 PM
242 Main St
Nov
21
OCW: Terminus
Nov 21, 2026 06:00 PM - 10:00 PM
Magma
25.00 USD
Dec
5
Photos with Santa
Dec 05, 2026 05:30 AM - 06:30 AM
160 Main St
Gloucester, MA · Latest Local
Events
Upcoming
Weekend
New
Dec
5
Photos with Santa
Dec 05, 2026 05:30 AM - 06:30 AM
160 Main St
Dec
9
Beauport Hotel's Mistletoe Lounge: Jingle Bells & Cowboy Boots
Dec 09, 2026 01:00 PM - 04:00 PM
Beauport Hotel Gloucester
USD 18 to 162
Dec
13
Gloucester Elks 892 Annual Holiday Fair
Dec 13, 2026 05:00 AM - 10:00 AM
97 Atlantic Rd
Dec
13
Once Upon a Winter: Tales of Wonder Through a Child's Eyes
Dec 13, 2026 11:00 AM
Gloucester Unitarian Universalist Church
Dec
12
15th Annual Spruce Road Extravaganza
Dec 12, 2026 06:00 PM - 10:45 PM
Blue Collar Lobster Company
100.00 USD
Dec
2
Tree of Lights 2026: Cape Ann Ceremony
Dec 02, 2026 12:00 PM
BankGloucester
Dec
11
John Cafferty and The Beaver Brown Band
Dec 11, 2026 03:00 PM
The Cut Live
Dec
12
Middle Street Walking Tour
Dec 12, 2026 06:00 AM - 09:00 AM
27 Pleasant St
Nov
11
Veterans Bowl Free on 11/11
Nov 11, 2026 06:00 AM - 05:30 PM
Cape Ann Lanes
Nov
9
LIVE@!~ Gloucester vs Old Rochester Regional Field Hockey <livestream>
Nov 09, 2026 12:00 PM - 03:00 PM
Gloucester High School Theatre Program
Nov
20
Dead to the Core - November Show
Nov 20, 2026 03:00 PM
The Cut Live
Nov
29
Chanukah Pop Up Shop
Nov 29, 2026 08:00 AM
37 Main Street
Nov
12
Level Up Gloucester: Thursday Night Magic
Nov 12, 2026 01:00 PM - 05:00 PM
Gloucester Fraternity Club
Dec
6
Happy Holidays Half MerryThon & 5K
Dec 06, 2026 04:00 AM
Good Harbor Beach
Nov
21
Reiki Level One
Nov 21, 2026 05:00 AM - 01:00 PM
6 Lexington Ave.
Dec
4
5th Annual Parade of Trees
Dec 04, 2026 12:00 PM - Dec 06, 2026 02:00 PM
First Baptist Church
Dec
5
4th Annual Operation Keep Gloucester Warm
Dec 05, 2026 05:00 AM - 09:00 AM
Trinity Congregational Church
Dec
5
Special Jewelry Event! Diva Donna
Dec 05, 2026 06:00 AM - Dec 06, 2026 01:00 PM
242 Main St
Nov
21
OCW: Terminus
Nov 21, 2026 06:00 PM - 10:00 PM
Magma
25.00 USD
Nov
29
Holiday Sip and Shop at Cruiseport
Nov 29, 2026 05:00 AM - 11:00 AM
Cruiseport Gloucester
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