Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Trex Music Fest

 Fri, 01 May at 07:00 pm John Handley High School

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 pm James R. Wilkins, Jr. Athletic & Events Center

Valley Health 10K Race

 Sat, 02 May at 08:30 am John Handley High School

2026 Apple Blossom Grand Feature Parade Seats - Troop 9

 Sat, 02 May at 01:30 pm Market Street United Methodist USD 13 to 15

Malloy Toyota Country Music Party

 Sat, 02 May at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

Coronation of Queen Shenandoah

 Fri, 01 May at 01:30 pm John Handley High School

Contemporary Christian Concert presented by Clean Water of Virginia

 Sun, 03 May at 02:00 pm James R. Wilkins, Jr. Athletic & Events Center

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 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

Valley Pediatric Dentistry Family Fun Party

 Tue, 28 Apr at 05:00 pm James R. Wilkins, Jr. Athletic & Events Center

Apple Blossom Valley Health 10K and Shenandoah Valley Orthodontics Kids' Bloomin' Mile

 Fri, 01 May at 08:00 am John Handley High School

Peach Festival

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

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

Apple Blossom Firefighters Parade Seats26 - Troop 9

 Fri, 01 May at 05:00 pm Market Street United Methodist USD 8 to 10

Hop Blossom Craft Beer Festival 2026

 Sat, 06 Jun at 12:00 pm Old Town Winchester USD 7 to 39

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

Pack 46 Grand Feature Parade Seats

 Sat, 02 May at 01:30 pm Winchester USD 14

Apple Harvest Festival

Sat, 03 Oct at 11:00 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

Homestead Harvest Festival

Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Peaches & Beaches Festival

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

Apple Harvest Festival

 Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

66th Annual Apple Blossom Antique Car Meet

 Sat, 09 May at 08:00 am Jim Barnett Park

Queen's Ball and Dance Party

 Fri, 01 May at 08:30 pm 1300 Senseny Rd, Winchester, VA 22602-6418, United States

Kids Festival

Sat, 27 Jun at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Honeycrisp Festival

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

Bloomin' Brews & Boogie

 Fri, 01 May at 12:00 pm 145 N Loudoun St, Winchester, VA 22601-4717, United States

Taste of Community Food Truck Festival

 Sat, 16 May at 11:00 am 1460 University Dr, Winchester, VA 22601, United States

Patriotic Festival

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

Pickle-chester

 Sat, 29 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

VA250 Fireworks Celebration

 Sat, 11 Jul at 08:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Winchester Police Dept. 5th Annual Auto Show

 Sat, 23 May at 09:00 am 100 W Piccadilly St, Winchester, VA 22601-3916, United States

Flutterby Fairy Festival 2026

 Sat, 06 Jun at 10:00 am 740 Merrimans Ln Winchester, VA

Pumpkin Festival

 Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Pack 46 Firefighter's Parade Seats

 Fri, 01 May at 05:30 pm Winchester USD 11 to 12

2026 Winchester Greek Festival

Sat, 22 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

Beltane Luna Market 2026

 Sat, 09 May at 10:00 am 125 S. Loudoun Street, Winchester, VA

The All Access Dance Party | Apple Blossom Festival Weekend

 Fri, 01 May at 07:00 pm Backseat Events USA USD 18 to 77

Fall Harvest Festival

Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

2026 Shenandoah Apple Blossom Grand Feature Parade

 Sat, 02 May at 11:30 am Shenandoah Apple Blossom Festival®

Apple Pie Baking Contest

 Thu, 30 Apr at 09:00 am Marker-Miller Orchards Farm Market

Beltane Magic Market

 Sun, 03 May at 10:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

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

 Sat, 02 May at 07:00 pm Elks Club

Guest Reading: Kindred Roots Tarot

Fri, 08 May at 12:00 pm 125 S. Loudoun Street, Winchester, VA