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

Celtic Fest

 Old Town Winchester 14 Mar 2026
FESTIVALS

Strawberry Festival

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

Carter Myers Automotive Jimmy Buffett Tribute Show

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

An Evening with Stephane Wrembel

 Bright Box (Winchester, VA) 27 Feb 2026
MUSIC

Peaches & Beaches Festival

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

Cash Party

 250 Costello Dr, Winchester, VA 22602-4310, United States 21 Mar 2026
PARTIES

McDonald's Apple Blossom Gaming Festival

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

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

Guest Reading: Kindred Roots Tarot

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

The All Access Dance Party | Apple Blossom Festival Weekend

 Backseat Events USA 1 May 2026
FESTIVALS USD 18 TO 77

Paella Day

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

Dancing Thru the Decades

 Backseat Events 7 Feb 2026
FESTIVALS

Malloy Toyota Country Music Party

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

Trex Music Fest

 John Handley High School 1 May 2026
FIREWORKS

Miss Honorary Fire Chief Contest

 James Wood Middle School 14 Mar 2026
CONTESTS

United Bank Bloomin' Wine Fest

 Downtown Walking Mall 24 Apr 2026
FESTIVALS

6th Annual Nitro Spring Fling

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

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

 Bright Box Theater 3 May 2026
MUSIC

United Bank Bloomin' Wine Fest

 Downtown Walking Mall 25 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

The YDC Spring Spectacular

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

Bloomin' Wine Fest

 Backseat Events 23 Apr 2026
FESTIVALS

Chocolate Festival

 115 Wolfe St, 22601 7 Feb 2026
KIDS

Beltane Magic Market

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

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

Claudio's Pizzeria The Bloom Store

 Apple Blossom Mall 3 Apr 2026
FESTIVALS

Contemporary Christian Concert presented by Clean Water of Virginia

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

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

Apple Blossom Wine Festival

Taylor Pavillion Winchester Va 25 Apr 2026
FESTIVALS

Lunch & Learn: About Blooming Time

 901 Amherst St, Winchester, VA, United States, Virginia 22601 7 Apr 2026
FESTIVALS

Valley Pediatric Dentistry Family Fun Party

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