Festivals in Winchester

Check out happening festivals events all around Winchester, VA

United Bank Bloomin' Wine Fest

 Fri, 24 Apr at 03:00 pm Downtown Walking Mall

United Bank Bloomin' Wine Fest

 Sat, 25 Apr at 11:00 am Downtown Walking Mall

Malloy Toyota Country Music Party

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Trex Music Fest

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

Valley Health 10K Race

 Sat, 02 May at 08:30 am 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

Valley Pediatric Dentistry Family Fun Party

 Tue, 28 Apr at 05:00 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

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 pm James R. Wilkins, Jr. Athletic & Events Center

Coronation of Queen Shenandoah

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

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

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®

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Peaches & Beaches Festival

Sat, 01 Aug 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

66th Annual Apple Blossom Antique Car Meet

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

McDonald's Apple Blossom Gaming Festival

 Sat, 25 Apr at 10:00 am 608 Millwood Ave, Winchester, VA 22601-5167, United States

WVU Medicine Pickleball Tournament

 Fri, 24 Apr at 09:00 am 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

Cash Party

 Sat, 21 Mar at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

The YDC Spring Spectacular

Sat, 21 Mar at 12:00 pm 302 S Loudoun Street, Winchester, VA

Pickle-chester

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

Fiesta Latina

 Sun, 26 Apr at 11:00 am Winchester Sportsplex

Queen's Ball and Dance Party

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

VA250 Fireworks Celebration

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

Beltane Luna Market 2026

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

West Oaks Farm Market's 2026 Spring Vendor Fair

 Sat, 04 Apr at 09:00 am West Oaks Farm Market

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

The All Access Dance Party | Apple Blossom Festival Weekend

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

10th Annual Nitro Spring Fling

Sat, 21 Mar at 09:00 am 246 Sulky Dr., Winchester, VA, United States, Virginia 22602

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

 Fri, 01 May at 09:00 am Millwood Station Banquet Hall

Apple Pie Baking Contest

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

Claudio's Pizzeria The Bloom Store

 Fri, 03 Apr at 10:00 am Apple Blossom Mall

Record Store Day 2026 at Back to the Media

 Sat, 18 Apr at 09:00 am 48 South Loudoun St., Winchester, VA, United States, Virginia 22601

Symphony Orchestra

 Thu, 02 Apr at 07:30 pm 1460 University Dr, Winchester, VA, United States, Virginia 22601

Beltane Magic Market

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

Bloomin' Wine Fest

 Thu, 23 Apr at 07:00 pm Backseat Events

Lunch & Learn: About Blooming Time

 Tue, 07 Apr at 12:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Apple Blossom Wine Festival

Sat, 25 Apr at 03:00 pm Taylor Pavillion Winchester Va

Guest Reading: Kindred Roots Tarot

Sat, 04 Apr at 11:00 am 125 S. Loudoun Street, Winchester, VA

World Tai Chi & Qigong Day

Sat, 25 Apr at 10:00 am 740 Merriman's Ln Winchester VA 22601

Guest Reading: Kindred Roots Tarot

Sat, 18 Apr at 11:00 am 125 S. Loudoun Street, Winchester, VA

Teen Art Club: Apple Blossom

 Thu, 09 Apr at 04:30 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Guest Reading: Kindred Roots Tarot

Fri, 03 Apr at 12:00 pm 125 S. Loudoun Street, Winchester, VA

Guest Reading: Kindred Roots Tarot

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