Upcoming Live Music Events

Booty Vortex - Boston's Finest Funk and Disco Band at The Cut

 The Cut Live 11 Oct 2025
ENTERTAINMENT

The Warped Tour Band

 The Cut Live 10 Oct 2025
ENTERTAINMENT

Dead to the Core - Fall Tour

 The Cut Live 18 Oct 2025
MUSIC

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Upcoming Halloween Events

SKUNK HALLOWEEN AT THE CUT, with Liquid light Bros, and four special musical guests

The Cut Live 25 Oct 2025
MUSIC

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

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

Soul Rebel Project - The Halloween Show

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

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Upcoming Festivals Events

Renaissance Faire Day at Hammond Castle Museum

 Hammond Castle Museum 8 Nov 2025
KIDS

Cape Ann Makers Market at Magtoberfest 2025

 Magnolia Library and Community Center 12 Oct 2025
MUSIC

5th Annual Magtoberfest

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

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Upcoming Food & Drinks Events

The NONNAS Dinner

 2 Main St., Gloucester, MA, United States, Massachusetts 01930 19 Oct 2025
WORKSHOPS

O'Brien's OBoru @ Blue Collar Lobster

 Blue Collar Lobster Co. 26 Oct 2025
PARTIES

O'Brien's OBoru @ Blue Collar Lobster

 Blue Collar Lobster Co. 16 Nov 2025
PARTIES

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Upcoming Comedy Events

Madame Mozart: The Lacrimosa

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 10 Oct 2025
COMEDY

Edgar Allan Poe Double Header

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 25 Oct 2025
ART

Madame Mozart: The Lacrimosa

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 11 Oct 2025
COMEDY

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Trending Events in Gloucester

Trick-or-Treat at the Castle

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 30 Oct 2025
TRICK-OR-TREAT

Holiday Wreath Making

 232 Main Street, Gloucester, MA, United States, Massachusetts 01930 22 Nov 2025
HOLIDAY

Holiday Craft Night: Wooden Gnome Decorating

 Revive Wellness 7 Nov 2025
CRAFTS USD 39

East Veterans Holiday Craft Fair

 Veterans Memorial 13 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

Neon 90’s Thanksgiving Eve at Minglewood

 Minglewood Harborside 26 Nov 2025
THANKSGIVING

Autumn Breakfast 2025

 Beauport Hotel Gloucester 23 Oct 2025
HOLIDAY USD 0 TO 39

SOLD OUT - 2025 Goblin King Ball at Hammond Castle Museum

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

Restorative Gentle Somatic Yoga® Workshop

 3A Pond Road, Gloucester, MA, United States, Massachusetts 01930 17 Oct 2025
HEALTH-WELLNESS

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

 The Cut Live 7 Nov 2025
ENTERTAINMENT

LIVE FROM THE LOUNGE - Jake Pardee

 8 Washington St, Gloucester, MA 01930-5734, United States 11 Oct 2025
PERFORMANCES

Cape Ann Plein Air 2025 Gala and Art Sale

North Shore Arts Association 10 Oct 2025
ART

Edgar Allan Poe Double Header

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 24 Oct 2025
ART

Undone

 Movement Arts Gloucester MA 25 Oct 2025
ENTERTAINMENT USD 0 TO 31

DMTB - A Celebration of Dave Matthews Band

 The Cut Live 14 Nov 2025
MUSIC

Live Band Karaoke Showcase with Groove Therapy - hosted by DJ Lou

 The Cut Live 17 Oct 2025
MUSIC

More things to do in Gloucester

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