Upcoming Events in Gloucester

Rock & Roll Circus Benefit Concert Starring Jon Butcher, James Montgomery, and Danny Klein

 The Cut Live 7 Nov 2025
ENTERTAINMENT

Kevin Coan - World Renowned Spirit Medium

 Capt. Lester S. Wass American Legion Post 3 29 Nov 2025

Motor Booty Affair

 The Cut Live 1 Nov 2025
ENTERTAINMENT

Way Up South at Minglewood Harborside Gloucester, MA Sat Nov 1st

 Minglewood Harborside 1 Nov 2025

Autumn Song Swap with Miranda Aisling, Matt Jenson, and Kara Kulpa

 11 Pleasant St., Suite 64, Gloucester, MA, United States, Massachusetts 01930 9 Nov 2025
MUSIC

HOLIDAYS & WINTERTIDE A night of Christmas and Winter Music

 The Cut Live 13 Dec 2025
MUSIC

Fast Times - 80’s Music

 The Cut Live 8 Nov 2025
ENTERTAINMENT

Private event- DJ holiday party

 Beauport Hotel Gloucester 12 Dec 2025
HOLIDAY

BrassFed Nation's Holiday Bash

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

Deb Hardy and Friends Featuring Brian King and Alyce Underhill

 Gloucester Unitarian Universalist Church 8 Nov 2025
MUSIC

Renaissance Faire Day at Hammond Castle Museum

 Hammond Castle Museum 8 Nov 2025
KIDS

Foot Zoning 101

 6 Lexington Ave., Magnolia, MA, United States, Massachusetts 01930 8 Nov 2025
WORKSHOPS

Holiday Craft Night: Wooden Gnome Decorating

 Revive Wellness 7 Nov 2025
CRAFTS USD 39

Once An Outlaw with The Peacheaters

 The Cut Live 15 Nov 2025
MUSIC

A Holiday Evening with Chelsea Berry

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 7 Dec 2025
MUSIC

Cape Ann Shakespeare Troupe presents: Two Gentlemen of Verona by William Shakespeare

 Capt. Lester S. Wass American Legion Post 3 14 Nov 2025
MUSIC

#TeamBenson GOTV Visibility

 St. Peter's Square 1 Nov 2025

Those Who Served - Korean, Vietnam & Cold War Veterans Portraits & Stories

 Gloucester City Hall 8 Nov 2025

LIVE FROM THE LOUNGE - Ye Olde Mitchells

 Capt. Lester S. Wass American Legion Post 3 8 Nov 2025

DMTB - A Celebration of Dave Matthews Band

 The Cut Live 14 Nov 2025
MUSIC

More things to do in Gloucester

Live Music
Halloween
Christmas Markets & Fairs
Christmas Wreath Workshops
Comedy
Trick Or Treat
Festivals
Food & Drinks
Thanksgiving
Job Fairs
Food Truck Festivals
Parades