Apple Harvest Festival Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 FESTIVALS
Pride at the MSV with Winchester Pride Sat, 03 Oct at 10:00 am Museum of the Shenandoah Valley FOOD-DRINKS
Apple Harvest Festival Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
2026 Wings and Wheels presented by United Bank - Winchester, VA Sat, 03 Oct at 10:00 am Winchester Regional Airport - OKV CAR-SHOWS
4th Annual Veterans Festival presented by Capon Valley Bank at Backseat Events! Sat, 19 Sep at 11:00 am 114 Full House Drive , Winchester, VA, United States, Virginia 22603 FESTIVALS
Native Plant Festival Sat, 03 Oct at 10:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601 FESTIVALS
Trunk or Treat on Loudoun Street Sat, 17 Oct at 02:30 pm 302 S Loudoun Street, Winchester, VA HALLOWEEN
Come Back To Earth: Mac Miller Live Band Tribute Sat, 19 Sep at 08:00 pm Bright Box (Winchester, VA) MUSIC
American Tune: Simon, Croce, & Taylor with Tom Glynn Sun, 27 Sep at 07:00 pm Bright Box (Winchester, VA) MUSIC
Little Black Dress Party to Benefit Chain of Checks Fri, 25 Sep at 07:00 pm Bright Box (Winchester, VA) NONPROFIT
Commanders Watch Party Sun, 20 Sep at 03:00 pm 329 N Cameron St # 200, Winchester, VA, United States, Virginia 22601 PARTIES
WINCHESTER VA - MID ATLANTIC REPTILE EXPO Sat, 26 Sep at 09:00 am Winchester Sports & Event Center BUSINESS
Addicted to Hope 2026 Sat, 03 Oct at 04:00 pm 329 N Cameron St, Winchester, VA 22601-4805, United States ART
Soar & Explore Block Party Mon, 21 Sep at 10:00 am 19 W Cork St, Winchester, VA, United States, Virginia 22601 HEALTH-WELLNESS
An Evening of Magic with David Anthony - 7PM Show Fri, 02 Oct at 07:00 pm Bright Box (Winchester, VA) MAGIC-SHOW
K-Pop Demon Hunters Family Friendly Dj show! - 5 and under free entry! Sun, 27 Sep at 12:30 pm Bright Box (Winchester, VA) KIDS
Passport to Discovery - Shenandoah Valley Discovery Museum's Annual Gala Sat, 26 Sep at 07:00 pm 19 W Cork St, Winchester, VA, United States, Virginia 22601 MUSIC
Homestead Harvest Festival Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 FESTIVALS
Pumpkin Festival Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
FemininiTea Tue, 06 Oct at 11:00 am The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA USD 55 FITNESS
Addicted to Hope - Brandon Novak - Meet and Greet Sat, 03 Oct at 06:30 pm 329 N Cameron St FREE FITNESS
Farm-to-Table Harvest Dinner with Chef Brandon Milhon Sat, 17 Oct at 06:00 pm Patti's Place USD 49 TO 97 FITNESS
Fall Harvest Festival Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 HARVEST-FESTIVAL
2026 YES Conference (Youth Empowered for Success) Tue, 20 Oct at 09:00 am Halpin-Harrison Hall USD 39 FITNESS
Winchester Swing Dance Lesson & Social Dancing Thu, 24 Sep at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601
Midnight Margaritas: Practical Magic 2 at Alamo Drafthouse Mon, 21 Sep at 06:00 pm Alamo Drafthouse Winchester (Winchester, VA) TRIPS-ADVENTURES
Petco Day at the WASPCA Sat, 20 Jun 111 Featherbed Lane, Winchester, VA, United States, Virginia 22601
The YDC's 2026 Festival of Trees Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA FESTIVALS
See How They Run at Winchester Little Theatre Inc. Sat, 19 Sep at 08:00 pm Winchester Little Theatre Inc. ART
Walk For Alopecia, National Alopecia Areata Foundation - Winchester, VA Sat, 26 Sep at 09:00 am Jim Barnett Park CHARITIES
Free Winchester, VA Homebuyer Workshop I Ready, Set, Own Sat, 17 Oct at 10:00 am Handley Regional Library FREE FITNESS
Samhain Magic Market Sun, 04 Oct at 10:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 NONPROFIT
Fort Collier Open House 2026 Sat, 19 Sep at 09:00 am 922 Martinsburg Pike, Winchester, VA, United States, Virginia 22601
CONFLUENCE-2026 The Washington International Young Artists Music Series Sat, 19 Sep at 02:30 pm Goodson Chapel – Recital Hall FREE FITNESS
Oktoberfest Presented by Alesatian Brewing Company Sat, 26 Sep at 12:00 pm The Newberry Building USD 13 TO 18 FITNESS
Women Entrepreneurs Coffee Networking Event Wed, 23 Sep at 08:30 am HIVE — Hub for Innovators, Veterans and Entrepreneurs FREE FITNESS
WOW Warrior Walk Chain of Blessings: Fundraiser for The Laurel Center Tue, 13 Oct at 11:00 am The George Washington A Wyndham Grand Hotel USD 34 TO 82 FITNESS
SPOOKY RIDDIM HOURS - HALLOW'S EVE EDITION Fri, 30 Oct at 08:00 pm Bright Box Theater USD 13 TO 29 HALLOWEEN
Third Battle of Winchester 162nd Anniversary Tours Sat, 19 Sep at 10:30 am Third Winchester Battlefield Park WORKSHOPS
4th Annual Winchester Zombie Walk Sun, 04 Oct at 02:00 pm 105 Millwood Ave, Winchester, VA, US NONPROFIT
Blessing of the Harvest Sat, 19 Sep at 02:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602
MURDER MYSTERY Paint Night "The Ravens Secret" at Easely Created Sat, 10 Oct at 05:00 pm Easely Created Winchester DRAWING-PAINTING
LAPTOP EVENT FOR VETERANS 10/16/26 Fri, 16 Oct at 09:00 am HIVE — Hub for Innovators, Veterans and Entrepreneurs FREE FITNESS
Local Boy Timmy @ Piccadilly's Public House and Restaurant in Winchester, Virginia Sat, 17 Oct at 07:30 pm Piccadilly's Public House and Restaurant PERFORMANCES
Spooktacular Scavenger Hunt For Charity Sat, 24 Oct at 04:00 pm Winchester Brew Works USD 17 TO 30 FITNESS
JILL FULTON BAND @ PICCADILLY'S Sat, 10 Oct at 07:30 pm Piccadilly's Public House and Restaurant MUSIC
Sept Guided Tour of Peaceful Fields Sanctuary Sun, 20 Sep at 02:00 pm Peaceful Fields Sanctuary USD 8 FITNESS
Celebrate Community Cats this Fall in Style Sun, 18 Oct at 02:00 pm The George Washington A Wyndham Grand Hotel USD 50 NONPROFIT
Fire and Rescue 5K Sat, 10 Oct at 08:00 am Village Square Restaurant and V2 Oyster Bar & Lounge SPORTS
Rainbow Connection Affinity Group Tue, 09 Jun 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601 NONPROFIT
Emo Night Karaoke 11/7 @ Bright Box Theater Sat, 07 Nov at 07:00 pm Bright Box Theater USD 20 FITNESS
Rusted Blue Sat, 26 Sep at 07:30 pm 125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 MUSIC
"Savings Saturday" $25 Paint Class 16x20 Canvas at Easely Created Sat, 03 Oct at 05:00 pm Easely Created Paint & DIY Studio WORKSHOPS
Willy Blaze And The Bad News Crew Sat, 19 Sep at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 MUSIC
Concern Hotline's 6th Annual Boo Kees Memorial Golf Tournament Fri, 09 Oct at 09:00 am Rock Harbor Golf Course SPORTS
Craft & Create at Chilly Hollow Brewery - Handknit Chunky Pumpkins Wed, 07 Oct at 06:00 pm Easely Created Winchester WORKSHOPS
Pride Kick-Off: Open Mic Fri, 02 Oct at 07:00 pm 124 W Piccadilly St, Winchester, VA 22601-3916, United States ART
Evening With The Babys Thu, 31 Dec at 08:30 pm The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA USD 162 FITNESS
SAVE THE DATE DIY Wooden Barn Quilt Class at Easely Created Sat, 10 Oct at 02:00 pm Easely Created Winchester WORKSHOPS
Commercial and multifamily investing masterclass + JV, team and syndication Tue, 13 Oct at 11:00 am 201 N Loudoun St FREE FITNESS
September Full Moon Night: Corn Moon Sat, 26 Sep at 05:00 pm 125 S. Loudoun Street, Winchester, VA MID-AUTUMN-FESTIVALS
Archives After Hours: Textiles Thu, 24 Sep at 05:30 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601
Monthly Menopause Wellness Circle Sun, 20 Sep at 12:00 pm 3042 Valley Ave #102, Winchester, VA, United States, Virginia 22602 HEALTH-WELLNESS
From Seed to Story | An Experience for the Woman Farmer Thu, 24 Sep at 03:00 pm Marker-Miller Orchards Farm Market BUSINESS
KIDS NIGHT OUT "SPOOKY HOUSE" AGES 6-12 at Easely Created Fri, 23 Oct at 05:30 pm Easely Created Winchester KIDS
251st USMC Ball Sat, 14 Nov at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 NONPROFIT
Community Appreciation Roadside Party at Liberty Tax Winchester Sat, 19 Sep at 11:00 am 30 Weems Ln, Winchester, VA 22601
Story Time on the Farm Tue, 23 Jun 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 KIDS
Winchester / Shenandoah Valley VA-PLA Networking Luncheon Thu, 15 Oct at 12:00 pm Paladin Downtown FREE FITNESS
Community Connect and Serve Tue, 29 Sep at 07:00 pm The Church of Jesus Christ of Latter-day Saints FREE FITNESS