Upcoming Events in Gloucester

Firebird Pops Orchestra Presents Christmas at the Castle

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025
ENTERTAINMENT

BrassFed Nation's Holiday Bash

 177 Main Street, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025
MUSIC

Cape Ann Big Band New Year’s Concert

 10 Church St, Gloucester, MA, United States, Massachusetts 01930 2 Jan 2026
ENTERTAINMENT

Holiday Drag Bingo

 1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930 19 Dec 2025
BINGO

Elemental Balancing Experience in the Salt Cave

 232 Main Street, Gloucester, MA, United States, Massachusetts 01930 27 Dec 2025
HEALTH-WELLNESS

An Enchanted Evening of Winter Solstice Ritual & Mediumship

 232 Main St 20 Dec 2025
HEALTH-WELLNESS USD 55

A Special Film Screening: TOWNIE, Starring Steve Sweeney

 The Cut Live 16 Jan 2026
ENTERTAINMENT

Battle of the Bands Alumni - Fundraiser for the Gloucester Public Schools Band Programs

 The Cut Live 27 Dec 2025
MUSIC

Santa Retruns to the Castle

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 14 Dec 2025

F-BOMB PRE-XMAS PARTY

 Minglewood Harborside 13 Dec 2025
CHRISTMAS

Dead to the Core - January Show

 The Cut Live 23 Jan 2026
MUSIC

An Enchanting Evening of Winter Solstice Ritual & Mediumship

 232 Main St 19 Dec 2025
HEALTH-WELLNESS USD 55

Deck the Halls by Candlelight at Hammond Castle Museum

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 18 Dec 2025
CANDLELIGHT-CONCERTS

Masshole Walking Group

 137 Main St, Gloucester, MA, United States, Massachusetts 01930 18 Dec 2025
DOG

Livin' On Luck at Salted Cod

 Salted Cod Arthouse & Wine Bar 13 Feb 2026
FREE

Acoustic View Bill Dwyer &Friends

 Snug Harbor Studio 39 Ye Olde County Rd Gloucester 20 Dec 2025
MUSIC

Deck the Halls at Hammond Castle Museum

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 14 Dec 2025
EXHIBITIONS

Last Minute Holiday Market at The Cut!

 177 E Main St, Gloucester, MA 01930-3801, United States 21 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

LIVE FROM THE LOUNGE - ToniAnn Enes

 8 Washington St, Gloucester, MA 01930-5734, United States 31 Jan 2026

Glitz & Glam NYE 2026 Party at Harbor 9

 Harbor 9 Golf & Sports Bar 31 Dec 2025
NEW-YEAR USD 29 TO 322

More things to do in Gloucester

Live Music
Christmas Light Displays
New Year
Christmas Markets & Fairs
Festivals
Pop-Ups
Halloween
Comedy
Christmas Wreath Workshops
Food Truck Festivals