Winchester Live Music Events

Dawg Days of Summer: Hot Dog Crawl

Old Town Winchester 22 Aug 2026

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026

16th Annual Patsy Cline Block Party

608 South Kent Street, Winchester, VA, United States, Virginia 22601 5 Sep 2026

Fiddles & Fifths 2026

Shenandoah Valley Civil War Museum 12 Sep 2026

Tyler Booth w/ James Tamelcoff

Bright Box Theater 22 Aug 2026

Friday Night West Oaks Farm Concert! Chris Darlington Band

4305 Middle Road, Winchester, VA, United States, Virginia 22602 21 Aug 2026

Struggle Jennings at Backseat Events

Backseat Events 10 Sep 2026

Honeycrisp Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 Sep 2026

Country. Patriotism. ALL the Hits. - Aaron Tippin LIVE

114 Full House Drive , Winchester, VA, United States, Virginia 22603 11 Sep 2026

Down on the Farm Dinner to Support Mutima Ministries

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 22 Aug 2026

Doyle Lawson and the Quicksilver Band

252 Costello Drive Winchester Va. 22602 12 Sep 2026

Aaron Tippin - Ages 16+

Backseat Events 11 Sep 2026

Hungry for History

Winchester-Frederick County Convention & Visitors Bureau 28 Aug 2026

Friday Night West Oaks Farm Concert! CAZHMIERE

4305 Middle Road, Winchester, VA, United States, Virginia 22602 18 Sep 2026

Apple Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 3 Oct 2026

Rodney Atkins in Winchester

Backseat Events 24 Oct 2026

Yappy Hour: Tail-Gate

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Sep 2026

Apple Harvest Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 10 Oct 2026

PICKLECHESTER! Dill Pickers at West Oaks Farm Market Saturday, August 29, 2026

West Oaks Farm Market 29 Aug 2026

2nd Annual Community Picnic

Willow Grove Farm 30 Aug 2026

Foreign Company at Back Seat Winchester Va.

Backseat Bar and Grill 26 Sep 2026

Austin Meade LIVE at Bright Box

Bright Box Theater 1 Oct 2026

Phil Zuckerman's Summer Rock Room Concert

Bright Box (Winchester, VA) 23 Aug 2026

Bluegrass on the Farm

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 9 Jul 2026

Bearded Harmony

4305 Middle Road, Winchester, VA, United States, Virginia 22602 28 Aug 2026

Passport to Discovery - Shenandoah Valley Discovery Museum's Annual Gala

19 W Cork St, Winchester, VA, United States, Virginia 22601 26 Sep 2026

Homestead Harvest Festival

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 24 Oct 2026

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Sevendust Tribute Show, feat. Illusion & Sonic Disciple @Backseat Events

Backseat Events USA 12 Sep 2026

Fall Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 17 Oct 2026

Evening With The Babys

The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA 31 Dec 2026

Local Boy Timmy @ Piccadilly's Public House and Restaurant in Winchester, Virginia

Piccadilly's Public House and Restaurant 17 Oct 2026

Emo Night Karaoke 11/7 @ Bright Box Theater

Bright Box Theater 7 Nov 2026

JILL FULTON BAND @ PICCADILLY'S

Piccadilly's Public House and Restaurant 10 Oct 2026

Saxsquatch

Backseat Events 23 Oct 2026

Odie and The Country Band at the Winchester Moose #1283

Winchester Moose Lodge 1283 23 Oct 2026

Little Ozzy: The Nation's Biggest Ozzy Tribute

114 Full House Drive , Winchester, VA, United States, Virginia 22603 28 Nov 2026

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 17 Oct 2026

Wichita Falls Band "Something about Sunday"

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 4 Oct 2026

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025

Local Boy Timmy @ Winchester Virginia Eagles Club 824

Eagle's Club Aerie #824 30 Oct 2026

Trainwreck LIVE at the Winchester Moose

Winchester Moose Family Center 1283 6 Nov 2026

Come From Away Musical Presented by Selah Theatre Project

302 N Braddock St 11 Jul 2026