Upcoming Food & Drinks Events

Second Glance Fashion Show: Thrift the Runway 2025

 The Cut - Stage • Studio • Restaurant • Bar 14 Sep 2025
FASHION USD 0 TO 34

Fall Harvest Dinner

 2 Main St., Gloucester, MA, United States, Massachusetts 01930 23 Sep 2025
WORKSHOPS

Lone Gull 10K Road Race - USATF Sanctioned

Good Harbor Beach 21 Sep 2025
SPORTS

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Upcoming Live Music Events

Hey Nineteen - A Tribute to Steely Dan

 The Cut Live 27 Sep 2025
MUSIC

Gavin Marengi Band w/s/g Nate Perry & Ragged Company

 177 Main Street, Gloucester, MA, United States, Massachusetts 01930 20 Sep 2025
MUSIC

Booty Vortex - Boston's Finest Funk and Disco Band

 The Cut Live 11 Oct 2025
ENTERTAINMENT

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Upcoming Comedy Events

THE FOOLS

 Capt. Lester S. Wass American Legion Post 3 20 Sep 2025
ENTERTAINMENT

Dueling Pianos

 The Cut Live 19 Sep 2025
ENTERTAINMENT

Gloucester Stage presents: MS. HOLMES & MS. WATSON – APT. 2B by Kate Hamill

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 18 Sep 2025
COMEDY

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Upcoming Festivals Events

Cape Ann Plein Air 2025 Gala and Art Sale

North Shore Arts Association 10 Oct 2025
ART

5th Annual Magtoberfest

 1 Lexington Ave, Gloucester, MA, United States, Massachusetts 01930 12 Oct 2025
FOOD-DRINKS

Cape Ann Makers Market at Magtoberfest 2025

 Magnolia Library and Community Center 12 Oct 2025
MUSIC

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Upcoming Halloween Events

SOLD OUT - 2025 Goblin King Ball at Hammond Castle Museum

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 24 Oct 2025
PARTIES

SAFETY - The Neverending Safety Show - 80s Fantasy & Magic

 177 Main Street, Gloucester, MA, United States, Massachusetts 01930 24 Oct 2025
ENTERTAINMENT

Phantom of the Opera with Live Accompaniment by Peter Krasinski

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 26 Oct 2025
ENTERTAINMENT

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Trending Events in Gloucester

The Backyard Growcery

 Burnham's Field, Gloucester, MA, United States, Massachusetts 01930 17 Sep 2025
FARMERS-MARKETS

Soul Rebel Project - The Halloween Show

 177 Main Street, Gloucester, MA, United States, Massachusetts 01930 31 Oct 2025
MUSIC

Black Uhuru

 The Cut Live 2 Oct 2025
ENTERTAINMENT

JoeNation Car Show

 148 Eastern Ave, Gloucester, MA, United States, Massachusetts 01930 21 Sep 2025
CAR-SHOWS

Spiritualism Tours by Candlelight

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

Bluegrass Music Sail - Joe Wilkins & The Clements Brothers

 63 Rogers St, Gloucester, MA, United States, Massachusetts 01930 21 Sep 2025

Fortune

 The Cut Live 26 Sep 2025
MUSIC

Nooks at Night

 75 Eastern Point Blvd, Gloucester, MA, United States, Massachusetts 01930 20 Sep 2025

The Warped Tour Band

 The Cut Live 10 Oct 2025
ENTERTAINMENT

Renaissance Faire Day at Hammond Castle Museum

 Hammond Castle Museum 8 Nov 2025
NONPROFIT

Exploring Blatchford’s Waterfront ✍️

 Cape Ann Museum Green, 13 Poplar St, Gloucester, MA 20 Sep 2025
SPORTS

Moss Henry Live at Lobsta Land

 Lobsta Land Restaurant 4 Oct 2025
MUSIC

Line's End @ The Rhumb Line: Sunday Funday

 The Rhumb Line 28 Sep 2025
MUSIC

GMGI Open House & Art Unveiling

 Gloucester Marine Genomics Institute 16 Sep 2025
ART FREE

Ms. Holmes and Ms. Watson

 Gloucester Stage Company 13 Sep 2025
TRIPS-ADVENTURES

More things to do in Gloucester

Food & Drinks
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Comedy
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Halloween
Candlelight Concerts
Car Shows
Music Festivals
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