Live Music in Winchester

Check out happening live music events all around Winchester, VA

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 pm James R. Wilkins, Jr. Athletic & Events Center

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 pm James R. Wilkins, Jr. Athletic & Events Center

Sammy Kershaw in Winchester

 Fri, 20 Mar at 08:00 pm Backseat Events

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

 Thu, 30 Apr at 08:00 pm Shenandoah Apple Blossom Festival®

First Friday

 Fri, 07 Aug at 05:00 pm Old Town Winchester Walking Mall

The Travelin McCourys at Backseat Events

 Fri, 27 Mar at 08:00 pm Backseat Events

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Peaches & Beaches Festival

Sat, 01 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

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

Sat, 21 Mar at 07:00 pm Bright Box Theater

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

 Fri, 20 Mar at 07:30 pm Bright Box Theater

Tracy Byrd in Winchester

 Fri, 17 Apr at 07:00 pm

For Whom the Bell Tolls: The Four Horsemen

 Sat, 21 Mar at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Lovesong - The Cure Tribute w/ First Wave

 Sun, 29 Mar at 06:00 pm Bright Box Theater

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

 Sun, 03 May at 07:00 pm Bright Box Theater

Graham Barham in Winchester

 Sat, 02 May at 05:00 pm James R. Wilkins

West Oaks Bloomin' Brunch and Bubbly 2026

 Sun, 26 Apr at 10:30 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

90s & 00s Night @ Backseat Bar & Grill

 Sat, 18 Apr at 08:30 pm Backseat Bar and Grill

Jackyl — Chainsaws, Southern Rock and Loud Guitars

 Thu, 09 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

First Friday

 Fri, 05 Jun at 05:00 pm Old Town Winchester

Backseat Rocks with That Arena Rock Show

 Sat, 11 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Glow in the Dark Easter Egg Hunt (Adults Only)

 Fri, 03 Apr at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Empanadas & Wine Pairing

 Sat, 25 Apr at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

First Friday

 Fri, 03 Jul at 05:00 pm Old Town Winchester

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Country Nite @ Crooked Run Fermentation in Sterling, VA

 Sat, 28 Mar at 07:00 pm Bright Box Theater USD 18 to 82

First Friday

 Fri, 04 Sep at 05:00 pm Old Town Winchester

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Corks & Cakes

 Sat, 20 Jun at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Willie Watson

 Fri, 10 Apr at 07:00 pm Bright Box Theater - VA

Willows At Meadow Branch Young at Heart Dance

 Thu, 30 Apr at 11:00 am Millwood Station Banquet Hall

5AM Trio: Esoterra Tour

 Thu, 26 Mar at 08:00 pm Bright Box Theater

Greener Living Day

 Sat, 25 Apr at 10:00 am 302 S Loudoun Street, Winchester, VA

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

 Sat, 11 Apr at 08:00 pm Backseat Events

Country Music Party

 Fri, 01 May at 07:00 pm James R. Wilkins Jr. Athletics and Event Center

JILL FULTON BAND @ PICCADILLY'S

 Sat, 09 May at 07:30 pm Piccadilly's Public House and Restaurant

Concern Hotline presents: A Taste of Winchester

 Thu, 09 Apr at 05:30 pm Fox Meadow Barn

Symphony Orchestra

 Thu, 02 Apr at 07:30 pm 1460 University Dr, Winchester, VA, United States, Virginia 22601

The Crown College Choir Live at Lighthouse Baptist Church

 Wed, 25 Mar at 06:30 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603

Balance Campaign

 Wed, 18 Mar at 08:00 pm Bright Box Theater

Rosie Soul Returns to the Blue Fox!

Sat, 28 Mar at 07:00 pm Blue Fox Billiards

Sin City at Backseat Bar & Grill

Sat, 28 Mar at 08:30 pm Backseat Bar and Grill

Backseat Events | THUNDERSTRUCK

 Fri, 03 Apr at 08:00 pm Backseat Events

Winchester Elks - Tuff Luck Band

Sat, 25 Apr at 07:00 pm Fraternal Order of Elks Lodge 867

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

 Fri, 03 Jul at 07:00 pm Winchester Virginia Eagles Club 824

Open Music Jam on the Farm, Phelpsmore Lane

 Fri, 07 Aug at 06:00 pm 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

Tuba-Euphonium Studio

 Tue, 24 Mar at 07:30 pm Goodson Chapel Recital Hall

Combs Apple Blossom Party!

 Fri, 01 May at 12:00 pm Combs Wastewater Management