Gloucester Live Music Events

SKYDOG

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 13 Jun 2026

Food Truck Frenzy 2026

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

The Nighthawks May 30, 2026

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 30 May 2026

2026 Event & Vendor Tickets: Gloucester Wine Festival

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

Hustle Souls

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 6 Jun 2026

Grateful Jed June 27, 2026

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

Fireside Collective August 15, 2026

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

Willie Williams Band at Flat Iron Crossroads

7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 23 May 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

JD Simo and Luther Dickinson August 8, 2026

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

Live Music: Ami Baker

Duke’s Aloha Eats 26 Jun 2026

Live Music: Vines & Vinegar Duo

Duke’s Aloha Eats 29 May 2026

Live Music: Mason Brown Band

Duke’s Aloha Eats 3 Jul 2026

Live Music: Vines & Vinegar Duo

Duke’s Aloha Eats 31 Jul 2026

Live Music: Charlie Perger

Duke’s Aloha Eats 5 Jun 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