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

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

Bright Box (Winchester, VA) 21 Apr 2026

Carter Myers Automotive Jimmy Buffett Tribute Show

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

Peach Festival

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

Sunflower Festival

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

Tracy Byrd in Winchester

17 Apr 2026

NAACP Winchester Area Juneteenth 2026

Museum of the Shenandoah Valley 14 Jun 2026

Nitty Gritty Dirt Band at The Monument

The Monument 7 Jun 2026

First Friday

Old Town Winchester Walking Mall 7 Aug 2026

Apple Harvest Festival

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

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

Shenandoah Apple Blossom Festival® 30 Apr 2026

Graham Barham in Winchester

James R. Wilkins 2 May 2026

90s & 00s Night @ Backseat Bar & Grill

Backseat Bar and Grill 18 Apr 2026

Peaches & Beaches Festival

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

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

Bright Box Theater 3 May 2026

West Oaks Bloomin' Brunch and Bubbly 2026

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

Ambrogi Acres 2nd Annual 420 Event

Backseat Events 18 Apr 2026

Empanadas & Wine Pairing

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

First Friday

Old Town Winchester 5 Jun 2026

Honeycrisp Festival

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

Patriotic Festival

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

VA250 Fireworks Celebration

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

Mother’s Day Cheesecake Pairing

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

80s Prom Rescue Fundraiser

Backseat Events 30 May 2026

Corks & Cakes

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

America 250th Celebration Elks 867

Fraternal Order of Elks Lodge 867 3 Jul 2026

Greener Living Day

302 S Loudoun Street, Winchester, VA 25 Apr 2026

Willows At Meadow Branch Young at Heart Dance

Millwood Station Banquet Hall 30 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

Gunshine Live: No Limits, Just Rock

114 Full House Drive , Winchester, VA, United States, Virginia 22603 24 Apr 2026

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

Elks Club 2 May 2026

Bluegrass on the Farm

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

Winchester Elks - Tuff Luck Band

Fraternal Order of Elks Lodge 867 25 Apr 2026

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

Backseat Events USA 31 Jul 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

Combs Apple Blossom Party!

Combs Wastewater Management 1 May 2026