Winchester Live Music Events

Live Music Happening Next in Winchester, VA

Nitty Gritty Dirt Band at The Monument

 The Monument 7 Jun 2026
MUSIC

Bryan Martin in Winchester

 Backseat Events 28 May 2026

Strawberry Festival

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

Rodney Atkins in Winchester

 Backseat Events 24 Oct 2026
ENTERTAINMENT

Peach Festival

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

NAACP Winchester Area Juneteenth 2026

 Museum of the Shenandoah Valley 14 Jun 2026
JUNETEENTH

Sunflower Festival

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

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
OPEN-MIC

Strawberry Festival

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

Apple Harvest Festival

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

Apple Harvest Festival

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

First Friday

 Old Town Winchester 5 Jun 2026
FIRST-FRIDAY

VA250 Fireworks Celebration

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

Honeycrisp Festival

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

Peaches & Beaches Festival

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

Homestead Harvest Festival

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

80s Prom Rescue Fundraiser

 Backseat Events 30 May 2026
DOG

Dawg Days of Summer: Hot Dog Crawl

 Old Town Winchester 22 Aug 2026
MUSIC USD 34

Friday Night West Oaks Farm Concert! Chris Darlington Band

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

America 250th Celebration Elks 867

 Fraternal Order of Elks Lodge 867 3 Jul 2026
MUSIC

Patriotic Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 11 Jul 2026
FESTIVALS

Corks & Cakes

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

Friday Night West Oaks Farm Concert! CAZHMIERE

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

Winchester, VA @ Bright Box Theater

 Bright Box Theater 31 Jul 2026
PARTIES

Fall Harvest Festival

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

Yappy Hour: Tail-Gate

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

Emo Night Karaoke 7/25 @ Bright Box Theater

 Bright Box Theater 25 Jul 2026
KARAOKE USD 20

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

 Backseat Events USA 31 Jul 2026
USD 18

Murphy's Bluegrass Bandits

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 May 2026

Live Music with Rachel Brinkmeier

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 23 May 2026
MUSIC

Bluegrass on the Farm

 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 11 Jun 2026
MUSIC

Charlie Collins & Matthew Goodnough w/ Your Friend Death

 Bright Box Theater 23 May 2026

Live Music- Ryan Jewell

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

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

 Winchester Virginia Eagles Club 824 3 Jul 2026
MUSIC

Open Music Jam on the Farm, Phelpsmore Lane

 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 5 Jun 2026
MUSIC

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

 Bright Box Theater 22 Aug 2025
BINGO FREE