Winchester Festivals Events

Festivals Happening Next in Winchester, VA

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 James R. Wilkins, Jr. Athletic & Events Center 1 May 2026
ENTERTAINMENT

Cash Party

 250 Costello Dr, Winchester, VA 22602-4310, United States 24 Jan 2026
PARTIES

Carter Myers Automotive Jimmy Buffett Tribute Show

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

Strawberry Festival

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

66th Annual Apple Blossom Antique Car Meet

 Jim Barnett Park 9 May 2026
CAR-SHOWS

Kids Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 27 Jun 2026
FESTIVALS

FredCo Eats Restaurant Week 2026

 Various Locations Across Frederick County, Virginia 26 Jan 2026
WORKSHOPS

Beltane Luna Market 2026

 125 S. Loudoun Street, Winchester, VA 9 May 2026
FESTIVALS

Paella Day

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 28 Feb 2026
MUSIC

Malloy Toyota Country Music Party

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

Dancing Thru the Decades

 Backseat Events 7 Feb 2026
FESTIVALS

Winchester Celtic Festival 2026

 Downtown Walking Mall 14 Mar 2026
FESTIVALS

Miss Honorary Fire Chief Contest

 James Wood Middle School 14 Mar 2026
CONTESTS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 31 Jan 2026
FESTIVALS

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

 Bright Box Theater 3 May 2026
MUSIC

6th Annual Nitro Spring Fling

246 Sulky Dr., Winchester, VA, United States, Virginia 22602 21 Mar 2026
SPRING-BREAK

Beltane Magic Market

 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 3 May 2026

United Bank Bloomin' Wine Fest

 Downtown Walking Mall 25 Apr 2026
FESTIVALS

United Bank Bloomin' Wine Fest

 Downtown Walking Mall 24 Apr 2026
FESTIVALS

Ostara Magic Market

 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 15 Mar 2026

Queen's Ball and Dance Party

 1300 Senseny Rd, Winchester, VA 22602-6418, United States 1 May 2026
PARTIES

Bloomin' Wine Fest

 Backseat Events 23 Apr 2026
FESTIVALS

Trex Music Fest

 John Handley High School 1 May 2026
FIREWORKS

The YDC Spring Spectacular

302 S Loudoun Street, Winchester, VA 21 Mar 2026
KIDS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 4 Apr 2026
FESTIVALS

McDonald's Apple Blossom Gaming Festival

 608 Millwood Ave, Winchester, VA 22601-5167, United States 25 Apr 2026
CONTESTS

Valley Health 10K Race

 John Handley High School 2 May 2026
SPORTS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 18 Apr 2026
FESTIVALS

Contemporary Christian Concert presented by Clean Water of Virginia

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

Claudio's Pizzeria The Bloom Store

 Apple Blossom Mall 3 Apr 2026
FESTIVALS

WVU Medicine Pickleball Tournament

 1300 Senseny Rd, Winchester, VA 22602-6418, United States 24 Apr 2026
SPORTS

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

 Millwood Station Banquet Hall 1 May 2026
KIDS

Valley Pediatric Dentistry Family Fun Party

 James R. Wilkins, Jr. Athletic & Events Center 28 Apr 2026
ART