Gloucester Live Music Events

Food Truck Frenzy 2026

5644 George Washington Memorial Hwy, Gloucester, VA 23061-3749, United States 25 Jul 2026

2026 Gloucester Wine Festival Attendee & Vendor Tickets

Brent & Becky's 19 Sep 2026

Concerts On The Green

6504 Main St, Gloucester, VA, United States, Virginia 23061 11 Jun 2026

Rebecca Frazier & Band June 20, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 20 Jun 2026

Cris Jacobs July 11, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 11 Jul 2026

The Tidewinders Music @ Gloucester Brewing Company

6778 Main Street, Gloucester, VA 20 Jun 2026

Fireside Collective August 15, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 15 Aug 2026

Grateful Jed June 27, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 27 Jun 2026

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

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 22 Aug 2026

Live Music: Part Time Live at Damon's

Damon & Company 27 Jun 2026

FUELING THE FIGHT | Phillips Energy's Annual END ALZ Fundraising Kickoff

Gloucester Brewing Company 22 Jun 2026

Aint Sisters at Flat Iron Crossroads July 25, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 25 Jul 2026

JD Simo and Luther Dickinson August 8, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 8 Aug 2026

SEPT 05 RETRO at Damon & Co. \m/(^_^)\m/

Damon & Company 5 Sep 2026

Live Music: Part Time Live at Thousand Trails

Thousand Trails Chesapeake Bay 19 Jun 2026

JUL 11th RETRO at Damon & Co. \m/(^_^)\m/

Damon & Company 11 Jul 2026

Live Music: Ami Baker

Duke’s Aloha Eats 26 Jun 2026

Live Music: Vines & Vinegar Duo

Duke’s Aloha Eats 31 Jul 2026

Live Music: Ray Meeks

Duke’s Aloha Eats 14 Aug 2026

Live Music: Tre Smith Duo

Duke’s Aloha Eats 12 Jun 2026

Live Music: Mason Brown Band

Duke’s Aloha Eats 3 Jul 2026

Live Music: Tre Smith

Duke’s Aloha Eats 24 Jul 2026

Live Music: Lane Rice

Duke’s Aloha Eats 4 Sep 2026

Live Music: Lane Rice Duo

Duke’s Aloha Eats 10 Jul 2026