Winchester Live Music Events

Paul Anka in Winchester

Ohrstrom-Bryant Theatre 15 Aug 2026

Peach Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 8 Aug 2026

Rodney Atkins in Winchester

Backseat Events 24 Oct 2026

Sunflower Festival

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

Maybe It Was Winchester: An Evening with Pam Tillis

114 Full House Drive , Winchester, VA, United States, Virginia 22603 17 Sep 2026

Dawg Days of Summer: Hot Dog Crawl

Old Town Winchester 22 Aug 2026

First Friday

Old Town Winchester Walking Mall 7 Aug 2026

Fiddles & Fifths 2026

Shenandoah Valley Civil War Museum 12 Sep 2026

Evening With The Babys

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

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

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

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Apple Harvest Festival

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

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026

Doyle Lawson and the Quicksilver Band

252 Costello Drive Winchester Va. 22602 12 Sep 2026

16th Annual Patsy Cline Block Party

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

Apple Harvest Festival

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

Honeycrisp Festival

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

Friday Night West Oaks Farm Concert! Chris Darlington Band

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

Friday Night West Oaks Farm Concert! CAZHMIERE

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

Homestead Harvest Festival

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

Down on the Farm Dinner to Support Mutima Ministries

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

Prohibition Party w/ Blair Crimmins + the Hookers & The Hot Mamas

Bright Box Theater 31 Jul 2026

Crowded Streets - The Dave Matthews Band Experience presents: Dave and Tim

Bright Box Theater 8 Aug 2026

Winchester, VA @ Bright Box Theater

Bright Box Theater 31 Jul 2026

Fall Harvest Festival

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

Hungry for History

Winchester-Frederick County Convention & Visitors Bureau 28 Aug 2026

Emo Night Karaoke 11/7 @ Bright Box Theater

Bright Box Theater 7 Nov 2026

Yappy Hour: Tail-Gate

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

Rally On Valley - 5th Annual

2818 Valley Avenue, Winchester, VA, United States, Virginia 22601 15 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

Smugglers Moon

4305 Middle Road, Winchester, VA, United States, Virginia 22602 7 Aug 2026

Farm Concert- Chad Laughlin & Riley Kerns

4305 Middle Road, Winchester, VA, United States, Virginia 22602 14 Aug 2026

Little Ozzy: The Nation's Biggest Ozzy Tribute

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

Andrew Renner Live at the Half Note Lounge

103 E Piccadilly St, Winchester, VA, United States, Virginia 22601 31 Jul 2026

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

Piccadilly's Public House and Restaurant 17 Oct 2026

Valerie Smith - Maggie's Journal Historical Musical

Patsy Cline Theatre 1 Aug 2026

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

West Oaks Farm Market 29 Aug 2026

Six Strings & Bourbon

4305 Middle Road, Winchester, VA, United States, Virginia 22602 16 Aug 2026

Silvertung: The Red Tour! Feat. 12 Sins & Cursor

Backseat Events USA 31 Jul 2026

Trainwreck LIVE at the Winchester Moose

Winchester Moose Family Center 1283 6 Nov 2026

Fogg Band

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 31 Jul 2026

Bearded Harmony

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

2nd Annual Community Picnic

Willow Grove Farm 30 Aug 2026

GRAY MATTER @WINCHESTER MOOSE

Winchester Moose Lodge 1283 31 Jul 2026

The Robbie Limon band returns to Piccadillys!

Piccadilly's Public House and Restaurant 14 Aug 2026

Bluegrass on the Farm

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

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 17 Oct 2026

Chris Brunn Live!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 31 Jul 2026

Roaring 20's Prohibition Party

15 N Loudon St. Winchester, VA 22601 31 Jul 2026

Valerie Smith - Maggie’s Journal historical musical!

Winchester, Virginia 1 Aug 2026

Wichita Falls Band "Something about Sunday"

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

Homestead Harvest Festival

2502 N Frederick Pike, Winchester, VA 22603-4162, United States 24 Oct 2026

Family Day Gospel Concert

598 N Kent St, Winchester, VA 22601-5348, United States 1 Aug 2026

The Travelin McCourys - Ages 18+

Backseat Events 14 Aug 2026

Aaron Tippin - Ages 16+

Backseat Events 11 Sep 2026

Open Music Jam on the Farm, Phelpsmore Lane

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 7 Aug 2026

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025