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

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

Valley Health 10K Race

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

Trex Music Fest

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

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

2026 Apple Blossom Grand Feature Parade Seats - Troop 9

 Sat, 02 May at 01:30 pm Market Street United Methodist USD 13 to 15

Malloy Toyota Country Music Party

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

HoneyWay Apple Blossom Golf Classic

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

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

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 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

Bright Box Theater - Oliver Anthony, Davisson Brothers , Joey Davis Band, Draven Riffe

 Tue, 21 Apr at 06:30 pm Bright Box (Winchester, VA)

First Bank Men's Commonwealth Luncheon

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

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Contemporary Christian Concert presented by Clean Water of Virginia

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

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

Sunflower Festival

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

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Tracy Byrd at Backseat Events

 Fri, 17 Apr at 08:00 pm Backseat Events

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

Apple Blossom Firefighters Parade Seats26 - Troop 9

 Fri, 01 May at 05:00 pm Market Street United Methodist USD 8 to 10

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

First Friday

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

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

New Playground Grand Opening Event

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

Pack 46 Grand Feature Parade Seats

 Sat, 02 May at 01:30 pm Winchester USD 14

Artisan Market in Old Town

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

Cider Tastings & Orchard Tours

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

Jackyl — Chainsaws, Southern Rock and Loud Guitars

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

Tracy Byrd in Winchester

 Fri, 17 Apr at 07:00 pm

Peaches & Beaches Festival

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

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

90s & 00s Night @ Backseat Bar & Grill

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

66th Annual Apple Blossom Antique Car Meet

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

Navy Federal Credit Union Veterans Dinner Show

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

West Oaks Bloomin' Brunch and Bubbly 2026

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

Pickle-chester

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

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

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

WVU Medicine Pickleball Tournament

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

Valley Cycle Center Stag Luncheon

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

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

 Sat, 09 May at 09:00 am Bright Box (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

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Ballerina Nail & Spa Pumps and Pearls Ladies Party

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

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, 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

First Friday

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

Kids Festival

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

Taste of Community Food Truck Festival

 Sat, 16 May at 11:00 am 1460 University Dr, Winchester, VA 22601, United States

90s Throwback Party ft. Dj OPHIE

 Sat, 18 Apr at 09:00 pm Bright Box Theater

VA250 Fireworks Celebration

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

"Hit Me 90's One More Time!" Comedy Murder Mystery Show (7PM)

 Sat, 06 Jun at 07:00 pm Bright Box Theater

W.O.W. - April Networking Event

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

Queen's Ball and Dance Party

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

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 pm 4063 Middle Rd, 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

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

The Employer Expo - Regional Hiring Fair

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

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

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

WINCHESTER VA - MID ATLANTIC REPTILE EXPO

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

39th Loudoun Street Mile

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

Trex Fire Truck Rodeo, Antique Show & Kids' Activities

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

Corks & Cakes

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

SAVE THE DATE: Queer Prom - May 30th

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

Rise Orthodontic Studio Blossoms & Bubbles with Miss Apple Blossom

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

Beltane Luna Market 2026

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

Spring Equinox Luna Market 2026

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

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

Moon & Moss - Grand Opening Event

 Sat, 11 Apr at 11:00 am 102 S Loudoun St, Winchester, VA 22601-4722, United States

Willie Watson

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

America 250th Celebration Elks 867

 Fri, 03 Jul at 07:00 pm Fraternal Order of Elks Lodge 867

The All Access Dance Party | Apple Blossom Festival Weekend

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

Pack 46 Firefighter's Parade Seats

 Fri, 01 May at 05:30 pm Winchester USD 11 to 12

Car Show

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

2026 Winchester Greek Festival

Sat, 22 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

Mother's Day Brunch at Patti’s Place

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

Prayer Brunch presented by Knouse Foods Musselman's

 Fri, 01 May at 11:00 am Fellowship Bible Church

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

Willows At Meadow Branch Young at Heart Dance

 Thu, 30 Apr at 11:00 am Millwood Station Banquet Hall

Shenandoah Valley Orthodontics Kids' Bloomin' Mile Race

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

30 Years of The Reagan Years!

 Fri, 08 May at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

2026 Spring Third Winchester Battlefield 5k/10k/Half

 Sat, 25 Apr at 08:00 am 251 First Woods Dr, Winchester, VA 22603-5800, United States

The Amish Outlaws at Backseat Events

 Sat, 02 May at 08:00 pm Backseat Events

Blue Ridge Care Breakfast Walk

 Thu, 30 Apr at 08:00 am Museum of the Shenandoah Valley

Sip & Sourdough™ – WASPCA Benefit

 Sun, 19 Apr at 01:00 pm Winchester Area SPCA

Greener Living Day

 Sat, 25 Apr at 10:00 am 302 S Loudoun Street, Winchester, VA

Cooking with Kimchi

 Sun, 26 Apr at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Mabon Luna Market 2026

 Sat, 19 Sep at 10:00 am 125 S. Loudoun Street, Winchester, VA

2026 Shenandoah Apple Blossom Grand Feature Parade

 Sat, 02 May at 11:30 am Shenandoah Apple Blossom Festival®

WINCHESTER VA - MID ATLANTIC REPTILE EXPO

 Sat, 26 Sep at 09:00 am Winchester Sports & Event Center

Pierogies!

 Sat, 13 Jun at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

NICHOLAS PARÉ & THE JAGS (Opening 60 Minute Set), THAT ARENA ROCK SHOW at Backseat Event Center

 Sat, 11 Apr at 08:00 pm Backseat Events
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