Winchester Live Music Events

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Low Water Bridge Band

Bright Box (Winchester, VA) 25 Nov 2026

The Nighthawks!

Bright Box (Winchester, VA) 28 Nov 2026

Faith, Love and Laughter - A Country Christmas

252 Costello Drive Winchester Va. 22602 5 Dec 2026

Evening With The Babys

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

Picadilly's - Michelle & Jason Hannan

Picadilly's Brewpub Winchester Va 13 Nov 2026

Winchester Moose #1283 presents Odie and The Country Band

Winchester Moose Lodge 1283 5 Dec 2026

JUMPTOWN

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 14 Nov 2026

Little Ozzy: The Nation's Biggest Ozzy Tribute

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

Adam Bennett Live at the Half Note Lounge

103 E Piccadilly St, Winchester, VA, United States, Virginia 22601 27 Nov 2026

Dylan Woelfel Live at the Half Note Lounge

103 E Piccadilly St, Winchester, VA, United States, Virginia 22601 13 Nov 2026

Christmas at the Movies - Guildhall Winchester

Guildhall Winchester 23 Dec 2026

The Koffin Kats / Voodoo Glow Skulls / The Raging Nathans

Bright Box (Winchester, VA) 8 Dec 2026

Symphonic Band

Armstrong Concert Hall 6 Dec 2026

Barker & Schuster

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 20 Nov 2026

YDC Festival of Trees - STREST, LLC (Approved Vendor)

302 S Loudoun St, Winchester, VA 22601-4638, United States 21 Nov 2026

At The End Of May DEBUT SHOW

Granny's Place 21 Nov 2026

Michelle & Jason Hannan

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 13 Nov 2026

The Naghash Ensemble at Shenandoah University

Goodson Chapel – Recital Hall 10 Nov 2026

The Reflex: The Ultimate 80's Tribute Band - 18+

Bright Box Theater 19 Dec 2026

MJT

Bright Box Theater 19 Nov 2026

Country Nite at Bright Box Theater- Winchester, VA

Bright Box Theater 11 Dec 2026

Emo Night Karaoke 2/26 @ Bright Box Theater

Bright Box Theater 26 Feb 2027

SANTALLICA: An Emo, Pop-Punk, & Metalcore Christmas

Bright Box Theater 18 Dec 2026

Rich Ridgell

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 21 Nov 2026

Christmas Dinner and The FOGG Band

1730 Berryville Pike, Winchester, VA 19 Dec 2026

Local Boy Timmy @ Piccadilly's Public House and Restaurant

Piccadilly's Public House and Restaurant 3 Dec 2026

Matt Miller ~ Thursday Night Vibes

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 19 Nov 2026

The Broken Hearts: Tribute to Tom Petty & The Heartbreakers

Bright Box Theater 2 May 2027

TRIVIA: Music by the Decades!

160 N Loudoun St, Winchester, VA, United States, Virginia 22601 25 Nov 2026

Odie and The Country Band at The Winchester Eagles Aerie #824

Winchester Virginia Eagles Club 824 20 Feb 2027

Local Boy Timmy @ Piccadilly's Public House

Piccadilly's Public House and Restaurant 12 Feb 2027

A1A - Apple Blossom Festival - Winchester, Virginia

1188 Ralph Shockey Drive, Winchester, VA, 22602 US 30 Apr 2027

Little Texas at Backseat Events

Backseat Events 13 Nov 2026

NW Works Chimers

Armstrong Concert Hall 12 Dec 2026

CONTEMPO Touring Ensemble: Songs in Rotation

Armstrong Concert Hall 3 Dec 2026

Guitar Ensemble

Goodson Chapel Recital Hall 9 Nov 2026

Choral Ensembles: Sounds of the Season

Armstrong Concert Hall 5 Dec 2026

Miesha Herron

125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 7 Nov 2026

Terri Clark

Backseat Events 3 Dec 2026