Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Celtic Fest

 Sat, 14 Mar at 12:00 pm Old Town Winchester

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 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

Coronation of Queen Shenandoah

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

Peaches & Beaches Festival

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

An Evening with Stephane Wrembel

 Fri, 27 Feb at 08:00 pm Bright Box (Winchester, VA)

32nd Annual Valley Health Community Wellness Festival

 Sat, 28 Feb at 10:00 am Apple Blossom Mall

Hop Blossom Craft Beer Festival 2026

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

66th Annual Apple Blossom Antique Car Meet

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

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

McDonald's Apple Blossom Gaming Festival

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

Miss Honorary Fire Chief Contest

 Sat, 14 Mar at 07:00 pm James Wood Middle School

West Oaks Farm Market's 2026 Spring Vendor Fair

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

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

United Bank Bloomin' Wine Fest

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

The All Access Dance Party | Apple Blossom Festival Weekend

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

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

Guest Reading: Kindred Roots Tarot

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

Paella Day

 Sat, 28 Feb at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

Tasting with Misty Mountain Meadworks

 Sat, 14 Mar at 12:00 pm Murphy Beverage Company

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

Guest Reading: Kindred Roots Tarot

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

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

 Sun, 03 May at 07:00 pm Bright Box Theater

6 YEAR ANNIVERSARY CELEBRATION! Shawnee Springs “Winchester” Market

 Sat, 14 Mar at 07:00 am Shawnee Springs Market & Cannery (Winchester, VA)

10th Annual Nitro Spring Fling

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

Queen's Ball and Dance Party

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

The YDC Spring Spectacular

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

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

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

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

Contemporary Christian Concert presented by Clean Water of Virginia

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

Claudio's Pizzeria The Bloom Store

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

WVU Medicine Pickleball Tournament

 Fri, 24 Apr at 09:00 am 1300 Senseny Rd, Winchester, VA 22602-6418, United States

Ostara Magic Market

 Sun, 15 Mar 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

Fiesta Latina

 Sun, 26 Apr at 11:00 am Winchester Sportsplex

Beltane Magic Market

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

Valley Pediatric Dentistry Family Fun Party

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

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

World Tai Chi & Qigong Day

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

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, 06 Mar at 12:00 pm 125 S. Loudoun Street, Winchester, VA

Guest Reading: Kindred Roots Tarot

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