Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Hang 10 Car & Dog Wash Firefighters' Parade

 Fri, 01 May at 06:00 pm Old Town, Winchester

GloFiber Grand Feature Parade

 Sat, 02 May at 01:30 pm Old Town, Winchester

United Bank Bloomin' Wine Fest

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

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 pm James R. Wilkins, Jr. Athletic & Events Center

Trex Music Fest

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

West Oaks 7th Annual Adult Egg Hunt

 Sun, 29 Mar at 12:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Flashlight Egg Hunt

 Fri, 20 Mar at 06:30 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Valley Health 10K Race

 Sat, 02 May at 08:30 am John Handley High School

HoneyWay Apple Blossom Golf Classic

 Fri, 24 Apr at 12:00 pm Rock Harbor Golf Course

Contemporary Christian Concert presented by Clean Water of Virginia

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

Valley Pediatric Dentistry Family Fun Party

 Tue, 28 Apr at 05:00 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

Coronation of Queen Shenandoah

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

Sammy Kershaw in Winchester

 Fri, 20 Mar at 08:00 pm Backseat Events

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Tracy Byrd at Backseat Events

 Fri, 17 Apr at 08:00 pm Backseat Events

First Bank Men's Commonwealth Luncheon

 Fri, 01 May at 11:00 am Piccadilly's Public House and Restaurant

Partlow Insurance Sports Breakfast

 Sat, 02 May at 09:00 am James R. Wilkins, Jr. Athletic & Events Center

Hop Blossom Craft Beer Festival 2026

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

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

West Oaks Spring Vendor Fair 2026

 Sat, 04 Apr at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

First Friday

 Fri, 07 Aug at 05:00 pm Old Town Winchester Walking Mall

The Travelin McCourys at Backseat Events

 Fri, 27 Mar at 08:00 pm Backseat Events

Rhea Lana's of Winchester Spring/Summer Family Shopping Event!

 Wed, 18 Mar at 04:30 pm 221 Commonwealth Ct, Winchester, VA 22602, USA

Spring Bridal Expo 2026

 Sun, 22 Mar at 12:00 pm The George Washington Hotel

NAACP Winchester Area Juneteenth 2026

 Sun, 21 Jun at 12:00 pm Museum of the Shenandoah Valley

Peaches & Beaches Festival

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

MONOFLO Presents: Ben Chapman & Meg McRee + The Jared Stout Band & Ali Tod

Sat, 21 Mar at 07:00 pm Bright Box Theater

CASH UNCHAINED: The Ultimate Johnny Cash Experience w/ James Tamelcoff

 Fri, 20 Mar at 07:30 pm Bright Box Theater

Tracy Byrd in Winchester

 Fri, 17 Apr at 07:00 pm

The Darkside Experience: A Tribute to Pink Floyd

 Sat, 28 Mar at 08:00 pm Bright Box Theater

Cider Tastings & Orchard Tours

 Sat, 18 Apr at 11:00 am Shawnee Springs Market & Cannery

For Whom the Bell Tolls: The Four Horsemen

 Sat, 21 Mar at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Artisan Market in Old Town

 Fri, 24 Apr at 03:00 pm Old Town, Winchester

Lovesong - The Cure Tribute w/ First Wave

 Sun, 29 Mar at 06:00 pm Bright Box Theater

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

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

66th Annual Apple Blossom Antique Car Meet

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

McDonald's Apple Blossom Gaming Festival

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

Graham Barham in Winchester

 Sat, 02 May at 05:00 pm James R. Wilkins

West Oaks Bloomin' Brunch and Bubbly 2026

 Sun, 26 Apr at 10:30 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

New Playground Grand Opening Event

 Sat, 18 Apr at 11:00 am Winchester VA Parks and Recreation

Navy Federal Credit Union Veterans Dinner Show

 Wed, 29 Apr at 06:00 pm James R. Wilkins, Jr. Athletic & Events Center

90s & 00s Night @ Backseat Bar & Grill

 Sat, 18 Apr at 08:30 pm Backseat Bar and Grill

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

 Sat, 09 May at 09:00 am Bright Box (Winchester, VA)

WVU Medicine Pickleball Tournament

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

Kids Festival

Sat, 27 Jun at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Valley Health Business at the Bloom

 Wed, 29 Apr at 11:00 am James R. Wilkins, Jr. Athletic & Events Center

Jackyl — Chainsaws, Southern Rock and Loud Guitars

 Thu, 09 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Cash Party

 Sat, 21 Mar at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

First Friday

 Fri, 05 Jun at 05:00 pm Old Town Winchester

The YDC Spring Spectacular

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

Backseat Rocks with That Arena Rock Show

 Sat, 11 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Little Chefs Sauce Lab at Chick-fil-A

 Wed, 18 Mar at 04:00 pm Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, )

Glow in the Dark Easter Egg Hunt (Adults Only)

 Fri, 03 Apr at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Pickle-chester

 Sat, 29 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Empanadas & Wine Pairing

 Sat, 25 Apr at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Fiesta Latina

 Sun, 26 Apr at 11:00 am Winchester Sportsplex

Ballerina Nail & Spa Pumps and Pearls Ladies Party

 Mon, 27 Apr at 06:30 pm Bright Box (Winchester, VA)

First Friday

 Fri, 03 Jul at 05:00 pm Old Town Winchester

Little Chefs Sauce Lab at Chick-fil-A

 Wed, 18 Mar at 09:30 am Chick-fil-A Rutherford Crossing (Winchester, VA)

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Queen's Ball and Dance Party

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

Country Nite @ Crooked Run Fermentation in Sterling, VA

 Sat, 28 Mar at 07:00 pm Bright Box Theater USD 18 to 82

Valley Cycle Center Stag Luncheon

 Fri, 01 May at 11:45 am Winchester Cold Storage / WCS Logistics

Easter at Victory Church

 Sun, 05 Apr at 10:00 am 2870 Middle Rd, Winchester, VA, United States, Virginia 22601

Easter at Vibrant City Church (9:00 or 11:00am)

 Sun, 05 Apr at 11:00 am 35 E Jubal Early Drive, Winchester, VA, United States, Virginia 22601

VA250 Fireworks Celebration

 Sat, 11 Jul at 08:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

First Friday

 Fri, 04 Sep at 05:00 pm Old Town Winchester

Lincoln Reagan Dinner

 Sat, 28 Mar at 06:00 pm Winchester Country Club USD 0 to 1,602

Beltane Luna Market 2026

 Sat, 09 May at 10:00 am 125 S. Loudoun Street, Winchester, VA

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

West Oaks Farm Market's 2026 Spring Vendor Fair

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

39th Loudoun Street Mile

 Mon, 25 May at 08:00 am 1512 S Loudoun St, Winchester, VA 22601-4422, United States

SAVE THE DATE: Queer Prom - May 30th

 Sat, 30 May at 07:00 pm Museum of the Shenandoah Valley

Easter Sunday Service

 Sun, 05 Apr at 10:30 am 134 N. Loudoun St., Winchester, VA

Corks & Cakes

 Sat, 20 Jun at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Winchester Police Dept. 5th Annual Auto Show

 Sat, 23 May at 09:00 am 100 W Piccadilly St, Winchester, VA 22601-3916, United States

Flutterby Fairy Festival 2026

 Sat, 06 Jun at 10:00 am 740 Merrimans Ln Winchester, VA

The Employer Expo - Regional Hiring Fair

 Wed, 13 May at 01:00 pm James R. Wilkins, Jr. Athletic & Events Center

Easter Brunch at Patti’s Place

 Sat, 04 Apr at 11:00 am Patti's Place USD 45

Ultimate All-Nighter 2026

 Fri, 03 Apr at 07:00 pm Whats New Worship USD 55

W.O.W. - April Networking Event

 Tue, 14 Apr at 11:00 am The George Washington A Wyndham Grand Hotel USD 34 to 82

Stuff & adopt a Cow Kids spring event at Chick-fil-A Pleasant Valley Road

 Wed, 22 Apr at 03:00 pm Chick-fil-A USD 23

Spring Equinox Luna Market 2026

 Sat, 11 Apr at 10:00 am 125 S. Loudoun Street, Winchester, VA

Comedy Night at James Charles Winery

 Sat, 21 Mar at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

The All Access Dance Party | Apple Blossom Festival Weekend

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

Willie Watson

 Fri, 10 Apr at 07:00 pm Bright Box Theater - VA

WINCHESTER VA - MID ATLANTIC REPTILE EXPO

 Sat, 18 Apr at 09:00 am Winchester Sports & Event Center

Mother's Day Brunch at Patti’s Place

 Sun, 10 May at 11:00 am Patti's Place USD 45

Rise Orthodontic Studio Blossoms & Bubbles with Miss Apple Blossom

 Sun, 26 Apr at 02:30 pm Museum of the Shenandoah Valley

Car Show

 Sat, 18 Apr at 10:00 am Armel Elementary School

Easter Breads

 Sat, 28 Mar at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

March Madness

 Sat, 21 Mar at 12:00 am James R. Wilkins, Jr. Athletic & Events Center

Shenandoah Valley Orthodontics Kids' Bloomin' Mile Race

 Fri, 01 May at 04:00 pm John Handley High School
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