Winchester Live Music Events

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

James R. Wilkins, Jr. Athletic & Events Center 1 May 2026

Strawberry Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 23 May 2026

Carter Myers Automotive Jimmy Buffett Tribute Show

James R. Wilkins, Jr. Athletic & Events Center 30 Apr 2026

Sammy Kershaw in Winchester

Backseat Events 20 Mar 2026

Sunflower Festival

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

Nitty Gritty Dirt Band at The Monument

The Monument 7 Jun 2026

Jackyl in Winchester

Backseat Events 9 Apr 2026

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

Shenandoah Apple Blossom Festival® 30 Apr 2026

First Friday

Old Town Winchester Walking Mall 7 Aug 2026

The Travelin McCourys at Backseat Events

Backseat Events 27 Mar 2026

NAACP Winchester Area Juneteenth 2026

Museum of the Shenandoah Valley 14 Jun 2026

Peaches & Beaches Festival

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

MONOFLO Presents: Ben Chapman & Meg McRee + The Jared Stout Band & Ali Tod

Bright Box Theater 21 Mar 2026

Tracy Byrd in Winchester

17 Apr 2026

For Whom the Bell Tolls: The Four Horsemen

114 Full House Drive , Winchester, VA, United States, Virginia 22603 21 Mar 2026

Lovesong - The Cure Tribute w/ First Wave

Bright Box Theater 29 Mar 2026

Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers

Bright Box Theater 3 May 2026

Graham Barham in Winchester

James R. Wilkins 2 May 2026

West Oaks Bloomin' Brunch and Bubbly 2026

4305 Middle Road, Winchester, VA, United States, Virginia 22602 26 Apr 2026

90s & 00s Night @ Backseat Bar & Grill

Backseat Bar and Grill 18 Apr 2026

CASH UNCHAINED: The Ultimate Johnny Cash Experience w/ James Tamelcoff

Bright Box Theater 20 Mar 2026

Jackyl — Chainsaws, Southern Rock and Loud Guitars

114 Full House Drive , Winchester, VA, United States, Virginia 22603 9 Apr 2026

First Friday

Old Town Winchester 5 Jun 2026

Backseat Rocks with That Arena Rock Show

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

Glow in the Dark Easter Egg Hunt (Adults Only)

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 3 Apr 2026

Empanadas & Wine Pairing

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 25 Apr 2026

Ambrogi Acres 2nd Annual 420 Event

Backseat Events 18 Apr 2026

First Friday

Old Town Winchester 3 Jul 2026

Country Nite @ Crooked Run Fermentation in Sterling, VA

Bright Box Theater 28 Mar 2026

First Friday

Old Town Winchester 4 Sep 2026

Mother’s Day Cheesecake Pairing

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 9 May 2026

Corks & Cakes

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 20 Jun 2026

Willie Watson

Bright Box Theater - VA 10 Apr 2026

Willows At Meadow Branch Young at Heart Dance

Millwood Station Banquet Hall 30 Apr 2026

5AM Trio: Esoterra Tour

Bright Box Theater 26 Mar 2026

Greener Living Day

302 S Loudoun Street, Winchester, VA 25 Apr 2026

NICHOLAS PARÉ & THE JAGS (Opening 60 Minute Set), THAT ARENA ROCK SHOW at Backseat Event Center

Backseat Events 11 Apr 2026

Country Music Party

James R. Wilkins Jr. Athletics and Event Center 1 May 2026

JILL FULTON BAND @ PICCADILLY'S

Piccadilly's Public House and Restaurant 9 May 2026

Concern Hotline presents: A Taste of Winchester

Fox Meadow Barn 9 Apr 2026

Symphony Orchestra

1460 University Dr, Winchester, VA, United States, Virginia 22601 2 Apr 2026

The Crown College Choir Live at Lighthouse Baptist Church

2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 25 Mar 2026

Balance Campaign

Bright Box Theater 18 Mar 2026

Rosie Soul Returns to the Blue Fox!

Blue Fox Billiards 28 Mar 2026

Sin City at Backseat Bar & Grill

Backseat Bar and Grill 28 Mar 2026

Backseat Events | THUNDERSTRUCK

Backseat Events 3 Apr 2026

Winchester Elks - Tuff Luck Band

Fraternal Order of Elks Lodge 867 25 Apr 2026

The Eagles Club 824 presents Odie and The Country Band (members and invited guests only)

Winchester Virginia Eagles Club 824 3 Jul 2026

Open Music Jam on the Farm, Phelpsmore Lane

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

Tuba-Euphonium Studio

Goodson Chapel Recital Hall 24 Mar 2026

Combs Apple Blossom Party!

Combs Wastewater Management 1 May 2026