Entertainment events in Gloucester

Check out happening entertainment events all around Gloucester, VA

Abingdon Ruritan Club Seafood Festival

 Wed, 20 May 8784 Guinea Road, Hayes, VA, USA Free

Symphony Under the Stars

 Sat, 06 Jun at 06:00 pm Walter Reed Way, Gloucester, VA 23061, United States

SKYDOG

 Sat, 13 Jun at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

90's Theme Trivia Night at Gloucester Brewing Company

 Sat, 02 May at 06:00 pm 6778 Main Street, Gloucester, VA, United States, Virginia 23061

The Nighthawks May 30, 2026

 Sat, 30 May at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Food Truck Frenzy 2026

 Sat, 25 Jul at 11:00 am 5644 George Washington Memorial Hwy, Gloucester, VA 23061-3749, United States

Florencia & the Feeling May 2, 2026

 Sat, 02 May at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Willie Williams Band May 23, 2026

 Sat, 23 May at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Hustle Souls

 Sat, 06 Jun at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Fireside Collective August 15, 2026

 Sat, 15 Aug at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Grateful Jed June 27, 2026

 Sat, 27 Jun at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

BBQ & Beats

 Sun, 24 May at 04:00 pm Damon & Company USD 15 to 50

Guilty FIXX Returns to Damon & Company Sports Bar & Grill

 Sat, 16 May at 09:30 pm Damon's Sports Bar & Grill

The Gabe Stillman Band with Special Guest Bobby Blackhat August 22, 2026

 Sat, 22 Aug at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

Reggae Rise Up at Flat Iron Crossroads May 16, 2026

 Sat, 16 May at 06:00 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

JD Simo and Luther Dickinson August 8, 2026

 Sat, 08 Aug at 06:30 pm 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061

LIVE MUSIC: Part Time Live at Mi Casa Azteca Mexican Restaurant Cantina

 Sat, 02 May at 09:00 pm Mi Casa Azteca Mexican Restaurant & Cantina

Fine Arts Museum of Gloucester concert (free)

 Wed, 27 May at 07:00 pm 6894 Main St, Gloucester, VA 23061, United States

Kids Movie Night

 Fri, 15 May at 05:30 pm Gloucester-Mathews Humane Society

Live Music: Phil Poteat

 Fri, 22 May at 07:00 pm Duke’s Aloha Eats

Live Music: Vines & Vinegar Duo

 Fri, 29 May at 07:00 pm Duke’s Aloha Eats

Live Music: Charlie Perger

 Fri, 05 Jun at 07:00 pm Duke’s Aloha Eats

Live Music: Mason Brown Band

 Fri, 03 Jul at 07:00 pm Duke’s Aloha Eats

Parking Lot Party

Thu, 21 May at 04:00 pm 7356 Walker Avenue, Gloucester, VA

Bookish Bingo

 Fri, 08 May at 06:00 pm 6619 Main Street, Gloucester, VA, United States, Virginia 23061