Winchester Festivals Events

United Bank Bloomin' Wine Fest

Downtown Walking Mall 24 Apr 2026

United Bank Bloomin' Wine Fest

Downtown Walking Mall 25 Apr 2026

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Valley Health 10K Race

John Handley High School 2 May 2026

2026 Apple Blossom Grand Feature Parade Seats - Troop 9

Market Street United Methodist 2 May 2026

Trex Music Fest

John Handley High School 1 May 2026

Malloy Toyota Country Music Party

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

Coronation of Queen Shenandoah

John Handley High School 1 May 2026

Strawberry Festival

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

Carter Myers Automotive Jimmy Buffett Tribute Show

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

Valley Pediatric Dentistry Family Fun Party

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

Peach Festival

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

Contemporary Christian Concert presented by Clean Water of Virginia

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

Sunflower Festival

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

NAACP Winchester Area Juneteenth 2026

Museum of the Shenandoah Valley 14 Jun 2026

Hop Blossom Craft Beer Festival 2026

Old Town Winchester 6 Jun 2026

Apple Blossom Firefighters Parade Seats26 - Troop 9

Market Street United Methodist 1 May 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

Pack 46 Grand Feature Parade Seats

Winchester 2 May 2026

Kids Festival

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

McDonald's Apple Blossom Gaming Festival

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

66th Annual Apple Blossom Antique Car Meet

Jim Barnett Park 9 May 2026

WVU Medicine Pickleball Tournament

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

Pickle-chester

4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 Aug 2026

Honeycrisp Festival

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

Taste of Community Food Truck Festival

1460 University Dr, Winchester, VA 22601, United States 16 May 2026

Queen's Ball and Dance Party

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

Winchester Police Dept. 5th Annual Auto Show

100 W Piccadilly St, Winchester, VA 22601-3916, United States 23 May 2026

Flutterby Fairy Festival 2026

740 Merrimans Ln Winchester, VA 6 Jun 2026

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

Millwood Station Banquet Hall 1 May 2026

2026 Winchester Greek Festival

1700 Amherst St, Winchester, VA, United States, Virginia 22601 22 Aug 2026

Beltane Luna Market 2026

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

The All Access Dance Party | Apple Blossom Festival Weekend

Backseat Events USA 1 May 2026

Pack 46 Firefighter's Parade Seats

Winchester 1 May 2026

Record Store Day 2026 at Back to the Media

48 South Loudoun St., Winchester, VA, United States, Virginia 22601 18 Apr 2026

2026 Shenandoah Apple Blossom Grand Feature Parade

Shenandoah Apple Blossom Festival® 2 May 2026

April TalkWALK - SU Campus & Connections

Winchester-Frederick County Visitors Center 20 Apr 2026

Bloomin' Wine Fest

Backseat Events 23 Apr 2026

Beltane Magic Market

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

Kubota Orange Days at Winchester Equipment

121 Indian Hollow Rd, Winchester, VA, United States, Virginia 22603 25 Apr 2026

Apple Blossom Wine Festival

Taylor Pavillion Winchester Va 25 Apr 2026

World Tai Chi & Qigong Day

740 Merriman's Ln Winchester VA 22601 25 Apr 2026

Guest Reading: Kindred Roots Tarot

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

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 8 May 2026