Upcoming Festivals Events

Valley Health 10K Race

 John Handley High School 2 May 2026
SPORTS

2026 Apple Blossom Grand Feature Parade Seats - Troop 9

 Market Street United Methodist 2 May 2026
FESTIVALS USD 13 TO 15

Malloy Toyota Country Music Party

 James R. Wilkins, Jr. Athletic & Events Center 2 May 2026
COUNTRY-MUSIC-FESTIVALS

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Upcoming Live Music Events

Rodney Atkins in Winchester

 Backseat Events 24 Oct 2026
ENTERTAINMENT

Bryan Martin in Winchester

 Backseat Events 28 May 2026

Peach Festival

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

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Upcoming Food & Drinks Events

Strawberry Festival

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

Sunflower Festival

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

NAACP Winchester Area Juneteenth 2026

 Museum of the Shenandoah Valley 14 Jun 2026
JUNETEENTH

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Upcoming Music Festivals Events

Homestead Harvest Festival

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

Apple Harvest Festival

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

Bloomin' Brews & Boogie

 145 N Loudoun St, Winchester, VA 22601-4717, United States 2 May 2026
MUSIC

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Trending Events in Winchester

The Employer Expo - Regional Hiring Fair

 James R. Wilkins, Jr. Athletic & Events Center 13 May 2026
BUSINESS

VA250 Fireworks Celebration

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

Pack 46 Grand Feature Parade Seats

 Winchester 2 May 2026
FESTIVALS USD 14

2026 Shenandoah Apple Blossom Grand Feature Parade

 Shenandoah Apple Blossom Festival® 2 May 2026
PARADES

Contemporary Christian Concert presented by Clean Water of Virginia

 James R. Wilkins, Jr. Athletic & Events Center 3 May 2026
CONCERTS

Partlow Insurance Sports Breakfast

 James R. Wilkins, Jr. Athletic & Events Center 2 May 2026
SPORTS

Nitty Gritty Dirt Band at The Monument

 The Monument 7 Jun 2026
MUSIC

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
OPEN-MIC

Apple Harvest Festival

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

66th Annual Apple Blossom Antique Car Meet

 Jim Barnett Park 9 May 2026
CAR-SHOWS

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

 Bright Box Theater 3 May 2026
MUSIC

Peaches & Beaches Festival

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

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

 Bright Box (Winchester, VA) 9 May 2026
POKEMON

Cole Chaney & Kyova w/ Brennan Edwards

 Bright Box Theater 6 May 2026
MUSIC

"Hit Me 90's One More Time!" Comedy Murder Mystery Show (7PM)

 Bright Box Theater 6 Jun 2026
COMEDY

More things to do in Winchester

Festivals
Live Music
Food & Drinks
Parades
Fireworks
Music Festivals
St. Patrick's Day
Speed Dating
Carnivals
Job Fairs
Food Truck Festivals