Gloucester Live Music Events

2026 Gloucester Wine Festival Attendee & Vendor Tickets

Brent & Becky's 19 Sep 2026

Davy Knowles And His Band Sept 19, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 19 Sep 2026

RiverJam Music Festival 2026

Arts on Main 12 Sep 2026

Fireside Collective August 15, 2026

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

Concerts On The Green

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

Tan and Sober Gentlemen September 26, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 26 Sep 2026

The Jared Stout Band October 3, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 3 Oct 2026

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

Damon & Company 5 Sep 2026

Live Music: Joshua Martin

Duke’s Aloha Eats 30 Oct 2026

JD Simo and Luther Dickinson August 8, 2026

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

OCT 03 RETRO at Damon & Co. \m/(^_^)\m/

Damon & Company 3 Oct 2026

SIPE, HADDEN, STERNBERG, COMBS August 29, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 29 Aug 2026

Flat Iron Crossroads

7709 Flat Iron Rd, Gloucester, VA 23061-5120, United States 10 Oct 2026

Live Music: Tre Smith Duo

Duke’s Aloha Eats 12 Jun 2026

Live Music: Ray Meeks

Duke’s Aloha Eats 14 Aug 2026

Live Music: Ami Baker

Duke’s Aloha Eats 23 Oct 2026

Live Music: Phil Poteat

Duke’s Aloha Eats 11 Sep 2026

Live Music: Vines & Vinegar Duo

Duke’s Aloha Eats 9 Oct 2026

Live Music: Ray Meeks

Duke’s Aloha Eats 16 Oct 2026

Live Music: Lane Rice

Duke’s Aloha Eats 4 Sep 2026

Josh Grigsby and County Line at Flat Iron Crossroads

Flat Iron Crossroads 10 Oct 2026