Winchester Festivals Events

Celtic Fest

Old Town Winchester 14 Mar 2026

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Carter Myers Automotive Jimmy Buffett Tribute Show

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

Strawberry Festival

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

Coronation of Queen Shenandoah

John Handley High School 1 May 2026

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026

An Evening with Stephane Wrembel

Bright Box (Winchester, VA) 27 Feb 2026

Hop Blossom Craft Beer Festival 2026

Old Town Winchester 6 Jun 2026

32nd Annual Valley Health Community Wellness Festival

Apple Blossom Mall 28 Feb 2026

66th Annual Apple Blossom Antique Car Meet

Jim Barnett Park 9 May 2026

Kids Festival

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

Cash Party

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

McDonald's Apple Blossom Gaming Festival

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

Miss Honorary Fire Chief Contest

James Wood Middle School 14 Mar 2026

West Oaks Farm Market's 2026 Spring Vendor Fair

West Oaks Farm Market 4 Apr 2026

VA250 Fireworks Celebration

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Jul 2026

Beltane Luna Market 2026

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

United Bank Bloomin' Wine Fest

Downtown Walking Mall 24 Apr 2026

The All Access Dance Party | Apple Blossom Festival Weekend

Backseat Events USA 1 May 2026

United Bank Bloomin' Wine Fest

Downtown Walking Mall 25 Apr 2026

Malloy Toyota Country Music Party

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

Guest Reading: Kindred Roots Tarot

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

Paella Day

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

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

Shenandoah Apple Blossom Festival® 30 Apr 2026

Tasting with Misty Mountain Meadworks

Murphy Beverage Company 14 Mar 2026

Record Store Day 2026 at Back to the Media

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

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

Bright Box Theater 3 May 2026

Guest Reading: Kindred Roots Tarot

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

6 YEAR ANNIVERSARY CELEBRATION! Shawnee Springs “Winchester” Market

Shawnee Springs Market & Cannery (Winchester, VA) 14 Mar 2026

10th Annual Nitro Spring Fling

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

Queen's Ball and Dance Party

1300 Senseny Rd, Winchester, VA 22602-6418, United States 1 May 2026

The YDC Spring Spectacular

302 S Loudoun Street, Winchester, VA 21 Mar 2026

Trex Music Fest

John Handley High School 1 May 2026

Valley Health 10K Race

John Handley High School 2 May 2026

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

Millwood Station Banquet Hall 1 May 2026

Contemporary Christian Concert presented by Clean Water of Virginia

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

Claudio's Pizzeria The Bloom Store

Apple Blossom Mall 3 Apr 2026

WVU Medicine Pickleball Tournament

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

Ostara Magic Market

105 Millwood Ave, Winchester, VA, United States, Virginia 22601 15 Mar 2026

Bloomin' Wine Fest

Backseat Events 23 Apr 2026

Beltane Magic Market

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

Valley Pediatric Dentistry Family Fun Party

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

Lunch & Learn: About Blooming Time

901 Amherst St, Winchester, VA, United States, Virginia 22601 7 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

Teen Art Club: Apple Blossom

901 Amherst St, Winchester, VA, United States, Virginia 22601 9 Apr 2026

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 6 Mar 2026

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 3 Apr 2026