Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 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

An Evening with Stephane Wrembel

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

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, 24 Jan at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

FredCo Eats Restaurant Week 2026

 Mon, 26 Jan at 07:00 am Various Locations Across Frederick County, Virginia

Beltane Luna Market 2026

 Sat, 09 May at 10:00 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

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Malloy Toyota Country Music Party

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

Miss Honorary Fire Chief Contest

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

Guest Reading: Kindred Roots Tarot

Sat, 31 Jan at 11:00 am 125 S. Loudoun Street, Winchester, VA

Winchester Celtic Festival 2026

 Sat, 14 Mar at 09:00 am Downtown Walking Mall

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

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

6th Annual Nitro Spring Fling

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

United Bank Bloomin' Wine Fest

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

Beltane Magic Market

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

Ostara Magic Market

 Sun, 15 Mar at 10:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

United Bank Bloomin' Wine Fest

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

The YDC Spring Spectacular

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

Queen's Ball and Dance Party

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

Bloomin' Wine Fest

 Thu, 23 Apr at 07:00 pm Backseat Events

Trex Music Fest

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

Guest Reading: Kindred Roots Tarot

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

Chocolate Festival

 Sat, 07 Feb at 11:00 am 115 Wolfe St, 22601

Guest Reading: Kindred Roots Tarot

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

McDonald's Apple Blossom Gaming Festival

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

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

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

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

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

Fiesta Latina

 Sun, 26 Apr at 11:00 am Winchester Sportsplex

Lunch & Learn: About Blooming Time

 Tue, 07 Apr at 12:00 pm 901 Amherst St, 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