Upcoming Live Music Events

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

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

Heavy Metal Horns - Live at The Cut Album Release Party

 177 Main Street, Gloucester, MA, United States, Massachusetts 01930 15 Aug 2025
ENTERTAINMENT

Blackburn Brew Fest

 Stage Fort Park 13 Sep 2025
FESTIVALS USD 10 TO 60

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Upcoming Comedy Events

SOLD OUT! Gloucester Rotary Comedy Show 2025

 Cruiseport Gloucester 28 Aug 2025
COMEDY

Preview #2: MS. HOLMES & MS. WATSON – APT. 2B by Kate Hamill

 267 E Main St, Gloucester, MA, United States, Massachusetts 01930 5 Sep 2025
COMEDY

THE FOOLS

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

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Upcoming Festivals Events

Gloucester Waterfront Festival

 Stage Fort Park 16 Aug 2025
FESTIVALS

Boat Parade of Lights

 The Hotel at Cape Ann Marina 30 Aug 2025
PARADES

Cape Ann Guitar Society Presents Fabiola Mendez

 The Cut Live 29 Aug 2025
MUSIC

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Upcoming Food & Drinks Events

Friday, August 15th, Sunset Sessions at Beauport Hotel

 Beauport Hotel Gloucester 15 Aug 2025
PARTIES USD 34 TO 322

Fish Tales Pub | King Saison

 Fish Tales Pub 23 Aug 2025
FESTIVALS

Saturday, August 16th, Sunset Sessions at Beauport Hotel

 Beauport Hotel Gloucester 16 Aug 2025
PARTIES USD 34 TO 322

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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

Soul Rebel Project - The Halloween Show

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

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Upcoming Music Festivals Events

Duane Betts & Palmetto Motel with Wood & Bone

 The Cut Live 31 Aug 2025
MUSIC

Mamadou at the Lanesville Music Festival

 8 Vulcan St, Gloucester, MA 01930-1125, United States 13 Sep 2025
MUSIC

A Night of Art Songs with Svetlana Sozdateleva

 House of Arts 16 Aug 2025
ART USD 45

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Trending Events in Gloucester

Spiritualism Tours by Candlelight

 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 14 Aug 2025
CANDLELIGHT-CONCERTS

41st Annual Gloucester Schooner Festival

 23 Harbor Loop, Gloucester, MA, United States, Massachusetts 01930 27 Aug 2025
FESTIVALS

Self-Care Social: Pop-Up

 Revive Wellness 23 Aug 2025
POP-UPS FREE

The Backyard Growcery

 Burnham's Field, Gloucester, MA, United States, Massachusetts 01930 13 Aug 2025
FARMERS-MARKETS

Saturday, August 30th, Labor Day Weekend Celebration at Beauport Hotel

 Beauport Hotel Gloucester 30 Aug 2025
LABOR-DAY USD 55 TO 322

Fireworks Cruise Gloucester (Labor Day Weekend) & Schooner Festival Viewing Cruises

 63 Rogers Street, Gloucester, MA, United States, Massachusetts 01930 27 Aug 2025
FIREWORKS

Jeff Fraser solo at the Beauport

Beauport Hotel Gloucester 21 Aug 2025

Live Music with Dennis Dulong

 75 Essex Ave (Rt. 133), Gloucester, MA, United States, Massachusetts 01930 24 Aug 2025
MUSIC

Back to the 80s live at The Cut

 The Cut Live 30 Aug 2025
MUSIC

Friday, August 29th, Sunset Sessions at Beauport Hotel

 Beauport Hotel Gloucester 29 Aug 2025
PARTIES USD 34 TO 322

The Rasa String Quartet

80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 24 Aug 2025
MUSIC

Hey Nineteen - A Tribute to Steely Dan

 The Cut Live 27 Sep 2025
MUSIC

Ripple In, Ripple Out

 Burnham's Field 13 Aug 2025
ART FREE

Neon 90’s at Blue Collar Lobster

 Blue Collar Lobster Co. 30 Aug 2025

51 ROCKY NECK Music Fridays

 51 Rocky Neck, Gloucester, MA, United States, Massachusetts 01930 15 Aug 2025
MUSIC

More things to do in Gloucester

Live Music
Comedy
Festivals
Food & Drinks
Labor Day
Pop-Ups
Halloween
Music Festivals
Parades
Candlelight Concerts