Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

Hop Blossom Craft Beer Festival 2026

 Sat, 06 Jun at 12:00 pm Old Town Winchester USD 9 to 39

Independence at the Park - Red, White, and Boom!

 Fri, 03 Jul at 12:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Red, White, & Lights! Drone Show

 Sat, 30 May at 09:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

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

Bryan Martin in Winchester

 Thu, 28 May at 08:00 pm Backseat Events

Peach Festival

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

NAACP Winchester Area Juneteenth 2026

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

KidzFest

 Sat, 13 Jun at 12:00 pm Old Town Winchester Walking Mall

Sunflower Festival

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

Pre-Release Club Tasting

 Fri, 17 Jul at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Chris Cagle at Backseat Events

 Fri, 29 May at 08:00 pm Backseat Events

First Friday

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

Strawberry Festival

 Sat, 23 May at 05:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 4305 Middle Rd, Winchester, VA 22602, United States

Apple Harvest Festival

Sat, 03 Oct 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

VIP Meet and Greet (General Admission Sold Separately)

 Thu, 04 Jun at 08:00 pm Backseat Events USA USD 82

First Friday

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

Samhain Luna Market 2026

 Sat, 31 Oct at 10:00 am 125 S. Loudoun Street, Winchester, VA

VA250 Fireworks Celebration

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

Honeycrisp Festival

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

Peaches & Beaches Festival

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

Homestead Harvest Festival

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

Flutterby Fairy Festival 2026

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

39th Loudoun Street Mile

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

Kids Festival

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

Celebracion of Winchester

Sat, 19 Sep at 12:00 pm Taylor Pavilion Winchester

ARE R.I.S.E Center's Inaugural Queer Book Fair

 Sat, 13 Jun at 01:00 pm 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

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

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

Calendar Girls at Winchester Little Theatre Inc.

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

DACK JANIELS Real Riddim Hours Anniversary Show

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

Friday Night West Oaks Farm Concert! Souled Out

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

Dawg Days of Summer: Hot Dog Crawl

 Sat, 22 Aug at 12:00 pm Old Town Winchester USD 34

12th Annual Splash Bash

 Sat, 30 May at 12:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Friday Night West Oaks Farm Concert! Chris Darlington Band

 Fri, 21 Aug at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

America 250th Celebration Elks 867

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

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, 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

Pumpkin Festival

 Sat, 24 Oct 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

The Healing Field of Honor

 Thu, 21 May at 03:00 pm John Handley High School

Corks & Cakes

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

Lebanese Wine Pairing Dinner at Byblos Winchester

 Sun, 12 Jul at 06:00 pm Byblos Winchester USD 77 to 87

2026 Winchester Greek Festival

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

Friday Night West Oaks Farm Concert! CAZHMIERE

 Fri, 18 Sep at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Winchester, VA @ Bright Box Theater

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

251st USMC Ball

 Sat, 14 Nov at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Pride Drag Show

 Sat, 27 Jun at 08:00 pm Winchester Brew Works USD 18

Revolutionary War Guided Walking and Trolley Tour of Winchester, Virginia

 Wed, 01 Jul at 05:15 pm 20 N Loudoun St USD 29

2026 Wings and Wheels - Winchester, VA

 Sat, 03 Oct at 10:00 am Winchester Regional Airport - OKV

Summer Of Love Scavenger Hunt For Charity

 Sat, 20 Jun at 04:00 pm Winchester Brew Works USD 17 to 30

Date Night Sip&Paint

 Fri, 12 Jun at 06:00 pm 16 S Loudoun St USD 34

Fall Harvest Festival

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

Paella Day

 Sat, 23 May at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Pierogies!

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

Fun in the Sun

 Sat, 18 Jul at 12:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Kisses For Charity!

 Sat, 30 May at 02:00 pm Peaceful Fields Sanctuary USD 13

Winchester Revolt: A Bike Ride Around Historic Winchester

 Sat, 06 Jun at 10:00 am Our Health USD 13

Yappy Hour: Tail-Gate

 Fri, 11 Sep at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

WINCHESTER VA - MID ATLANTIC REPTILE EXPO

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

2026 Third Winchester Battlefield 5k/10k/Half

 Sat, 08 Aug at 07:30 am 251 First Woods Dr, Winchester, VA 22603-5800, United States

Mabon Luna Market 2026

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

W.O.W. - June Networking Event

 Tue, 09 Jun at 11:00 am The George Washington A Wyndham Grand Hotel USD 34 to 82

Emo Night Karaoke 7/25 @ Bright Box Theater

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

Hop Phased Makers Market

Sat, 06 Jun at 12:00 pm 125 S. Loudoun Street, Winchester, VA

2026 Heatwave Hustle 5k/10k

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

Family Day Fishing Rodeo

 Sat, 13 Jun at 07:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

3rd Annual Navy Federal 5K - Winchester, VA

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

Fairytale on the Farm

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

2026 Vintage Offroad Nationals

 Fri, 11 Sep at 12:00 pm Adrenaline RC Raceway

Litha Luna Market 2026

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

Breaking Bread

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

Speed Dating & Ice Cream Social

 Fri, 19 Jun at 05:00 pm The Homestead Farm at Fruit Hill Orchard LLC USD 29

FemininiTea

 Tue, 06 Oct at 11:00 am The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA USD 55

Comedy to the Rescue

 Tue, 23 Jun at 05:30 pm 15 N Loudoun St, Winchester, VA 22601-4715, United States

MSGBR 80'S Prom Unleashed at Backseat Events

 Sat, 30 May at 07:00 pm Backseat Events

Bryan Martin at Backseat Events

 Thu, 28 May Backseat Events

Music Bingo

 Thu, 11 Jun at 07:30 pm 125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601

Effective Change Management 1-Day Course in Winchester, VA

 Fri, 22 May at 09:00 am Regus Center USD 654 to 861

Live Music: Chris Brunn

Fri, 22 May at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Bryan Martin

 Wed, 27 May at 07:00 pm Backseat Events

June Guided Tour of Peaceful Fields Sanctuary

 Sun, 28 Jun at 02:00 pm Peaceful Fields Sanctuary USD 8

Yoga in the Gardens

 Fri, 05 Jun at 09:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

COMMUNITY DANCE NIGHT -- Still Freee!

 Wed, 27 May at 07:00 pm 10 N Kent St, Winchester, VA, United States, Virginia 22601

TalkWALK Community Walks - June 2026

 Mon, 15 Jun at 06:00 pm 1 N Loudoun St Free

Samhain Magic Market

 Sun, 04 Oct at 10:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

Revival Vintage Co Grand Opening

Thu, 21 May at 11:00 am 3 S. Loudoun St. Winchester Va

Grow YOUR BUSINESS Without Limits

 Thu, 28 May at 11:00 am HIVE — Hub for Innovators, Veterans and Entrepreneurs Free

4th Annual Winchester Zombie Walk

 Sun, 04 Oct at 02:00 pm 105 Millwood Ave, Winchester, VA, US

Family Wellness & Water Safety Event

 Sat, 30 May at 09:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Yard Sale

 Sat, 13 Jun at 08:00 am 22 Clark St, Winchester, VA 22601-4848, United States

Mediumship Luna Market 2026

 Sat, 15 Aug at 11:00 am 125 S. Loudoun Street, Winchester, VA

BUSINESS RESOURCE FAIR

 Wed, 29 Jul at 11:00 am HIVE — Hub for Innovators, Veterans and Entrepreneurs Free

Murphy's Bluegrass Bandits

 Fri, 29 May at 05:30 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

From the Land of Spices: Indian Favorites III

 Sat, 23 May at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

“The Colored Patriot: The Un-Erased Story of Thomas Laws”

 Thu, 28 May at 06:00 pm 100 W Piccadilly St, Winchester, VA 22601-3916, United States

Sheet Pan Event

 Thu, 04 Jun at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
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