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

Bright Box Theater - Oliver Anthony, Davisson Brothers , Joey Davis Band, Draven Riffe

 Tue, 21 Apr at 06:30 pm Bright Box (Winchester, VA)

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Sunflower Festival

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

NAACP Winchester Area Juneteenth 2026

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

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

First Friday

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

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

Jackyl — Chainsaws, Southern Rock and Loud Guitars

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

Tracy Byrd in Winchester

 Fri, 17 Apr at 07:00 pm

Peaches & Beaches Festival

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

Graham Barham in Winchester

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

90s & 00s Night @ Backseat Bar & Grill

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

West Oaks Bloomin' Brunch and Bubbly 2026

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

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

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

Backseat Rocks with That Arena Rock Show

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

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

First Friday

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

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 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

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

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

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

Monolith, Breach the Silence, Ladder Match - Heavy Metal Night @ Bright Box

 Fri, 10 Apr at 07:00 pm Bright Box (Winchester, VA)

Country Music Party

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

Concern Hotline presents: A Taste of Winchester

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

JILL FULTON BAND @ PICCADILLY'S

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

Winchester Elks Lodge - Mack Berry Band (members & guest)

 Sat, 02 May at 07:00 pm Elks Club

Gunshine Live: No Limits, Just Rock

 Fri, 24 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Bluegrass on the Farm

 Thu, 11 Jun at 06:00 pm 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

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

Combs Apple Blossom Party!

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