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

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

Valley Health 10K Race

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

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

Coronation of Queen Shenandoah

 Fri, 01 May at 01:30 pm 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

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 pm James R. Wilkins, Jr. Athletic & Events Center

Rodney Atkins in Winchester

 Sat, 24 Oct at 07:00 pm Backseat Events

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Valley Pediatric Dentistry Family Fun Party

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

Bryan Martin in Winchester

 Thu, 28 May at 08:00 pm Backseat Events

Apple Blossom Valley Health 10K and Shenandoah Valley Orthodontics Kids' Bloomin' Mile

 Fri, 01 May at 08:00 am John Handley High School

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

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

Apple Blossom Firefighters Parade Seats26 - Troop 9

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

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

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

Pack 46 Grand Feature Parade Seats

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

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

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

Navy Federal Credit Union Veterans Dinner Show

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

First Friday

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

Valley Cycle Center Stag Luncheon

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

Apple Harvest Festival

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

Graham Barham in Winchester

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

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

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

Homestead Harvest Festival

Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Peaches & Beaches Festival

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

Apple Harvest Festival

 Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

66th Annual Apple Blossom Antique Car Meet

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

Queen's Ball and Dance Party

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

Free Comic Book Day 2026!

 Sat, 02 May at 10:00 am 80 Weems Ln, Winchester, VA, United States, Virginia 22601

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

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

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

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

Joshua Quimby & Matt Pless

 Sat, 16 May at 07:30 pm Bright Box Theater

Valley Health Business at the Bloom

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

Kids Festival

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

Queer Prom - May 30th TICKETS ON SALE NOW!

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

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

First Friday

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

Mother’s Day Cheesecake Pairing

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

Bloomin' Brews & Boogie

 Fri, 01 May at 12:00 pm 145 N Loudoun St, Winchester, VA 22601-4717, United States

Taste of Community Food Truck Festival

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

Patriotic Festival

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

Pickle-chester

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

VA250 Fireworks Celebration

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

39th Loudoun Street Mile

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

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

America 250th Celebration Elks 867

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

Flutterby Fairy Festival 2026

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

Pumpkin Festival

 Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

Corks & Cakes

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

Pack 46 Firefighter's Parade Seats

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

Blue Ridge Care Breakfast Walk

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

2026 Winchester Greek Festival

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

Prayer Brunch presented by Knouse Foods Musselman's

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

Beltane Luna Market 2026

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

The All Access Dance Party | Apple Blossom Festival Weekend

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

Friday Night West Oaks Farm Concert! Souled Out

 Fri, 19 Jun at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

DACK JANIELS Real Riddim Hours Anniversary Show

 Fri, 22 May at 08:00 pm Bright Box Theater USD 15 to 30

Winchester, VA @ Bright Box Theater

 Fri, 31 Jul at 09:00 pm Bright Box Theater

Mother's Day Brunch at Patti’s Place

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

Friday Night West Oaks Farm Concert! Robbie Limon Band

 Fri, 15 May at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Western Swing Dance Night

 Fri, 01 May at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Shenandoah Valley Orthodontics Kids' Bloomin' Mile Race

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

The Amish Outlaws at Backseat Events

 Sat, 02 May at 08:00 pm Backseat Events

Fall Harvest Festival

Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Emo Night Karaoke 7/25 @ Bright Box Theater

 Sat, 25 Jul at 07:00 pm Bright Box Theater USD 20

Country Music Party

 Fri, 01 May at 07:00 pm James R. Wilkins Jr. Athletics and Event Center

2026 Shenandoah Apple Blossom Grand Feature Parade

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

2000s Throwback Party Apple Blossom Edition 21+

 Sat, 02 May at 09:00 pm Bright Box (Winchester, VA)

Apple Pie Baking Contest

 Thu, 30 Apr at 09:00 am Marker-Miller Orchards Farm Market

Willows At Meadow Branch Young at Heart Dance

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

Pajama Party | Ladies Night Out

 Sat, 09 May at 06:00 pm The George Washington A Wyndham Grand Hotel USD 89 to 120

Calendar Girls at Winchester Little Theatre Inc.

 Sat, 23 May at 08:00 pm Winchester Little Theatre Inc.

30 Years of The Reagan Years!

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

WINCHESTER VA - MID ATLANTIC REPTILE EXPO

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

Live Music from Logan Moore

 Fri, 08 May at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Pierogies!

 Sat, 13 Jun at 04:30 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

Bloom After Dark w/ DJ OPHIE & DJ CURFEW

 Fri, 01 May at 09:00 pm Bright Box Theater

2026 Heatwave Hustle 5k/10k

 Sun, 28 Jun at 08:30 am 901 Amherst St, Winchester, VA 22601-3305, United States

Friday Night Fever Disco Dance Party

 Thu, 30 Apr at 07:00 pm James R. Wilkins Jr. Athletics and Event Center

Fairytale on the Farm

 Sat, 27 Jun at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

3rd Annual Navy Federal 5K - Winchester, VA

 Sat, 06 Jun at 08:00 pm 141 Security Drive Winchester, VA

The Souled Out Band - Katie's Backseat Bloom'n Dance Party at Backseat Events

 Thu, 30 Apr at 08:00 pm Backseat Events

Litha Luna Market 2026

 Sat, 20 Jun at 10:00 am 125 S. Loudoun Street, Winchester, VA

CNB Bank Ladies' Commonwealth Social

 Thu, 30 Apr at 03:00 pm The George Washington Hotel

W.O.W. - May Networking Event

 Tue, 12 May at 11:00 am The George Washington A Wyndham Grand Hotel USD 34 to 82

Bryan Martin

 Wed, 27 May at 07:00 pm Backseat Events

May Guided Tour of Peaceful Fields Sanctuary

 Sun, 17 May at 02:00 pm Peaceful Fields Sanctuary USD 8

Bloom Boom!

 Sat, 02 May at 07:00 pm 608 Millwood Ave, Winchester, VA 22601-5167, United States

Breaking Bread

 Sat, 13 Jun at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
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