Pride at the MSV with Winchester Pride Sat, 03 Oct at 10:00 am Museum of the Shenandoah Valley FOOD-DRINKS
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
Addicted to Hope 2026 Sat, 03 Oct at 04:00 pm 329 N Cameron St, Winchester, VA 22601-4805, United States ART
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
Addicted to Hope - Brandon Novak - Meet and Greet Sat, 03 Oct at 06:30 pm 329 N Cameron St FREE FITNESS
Fall Harvest Festival Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 HARVEST-FESTIVAL
Midnight Margaritas: Practical Magic 2 at Alamo Drafthouse Mon, 21 Sep at 06:00 pm Alamo Drafthouse Winchester (Winchester, VA) TRIPS-ADVENTURES
The YDC's 2026 Festival of Trees Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA FESTIVALS
Fort Collier Open House 2026 Sat, 19 Sep at 09:00 am 922 Martinsburg Pike, Winchester, VA, United States, Virginia 22601
Oktoberfest Presented by Alesatian Brewing Company Sat, 26 Sep at 12:00 pm The Newberry Building USD 13 TO 18 FITNESS
SPOOKY RIDDIM HOURS - HALLOW'S EVE EDITION Fri, 30 Oct at 08:00 pm Bright Box Theater USD 13 TO 29 HALLOWEEN
MURDER MYSTERY Paint Night "The Ravens Secret" at Easely Created Sat, 10 Oct at 05:00 pm Easely Created Winchester DRAWING-PAINTING
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
JILL FULTON BAND @ PICCADILLY'S Sat, 10 Oct at 07:30 pm Piccadilly's Public House and Restaurant MUSIC
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
September Full Moon Night: Corn Moon Sat, 26 Sep at 05:00 pm 125 S. Loudoun Street, Winchester, VA MID-AUTUMN-FESTIVALS
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
Katie's Country Music Fest Sat, 14 Nov at 08:00 pm Backseat Events USD 39 TO 135 COUNTRY-MUSIC-FESTIVALS
Joey Harkum (Love & Labor 10 Year Anniversary Celebration) w/ Ray Wroten Fri, 13 Nov at 08:00 pm Bright Box Theater FRIDAY-THE-13TH
Winchester Moose #1283 presents Odie and The Country Band Sat, 05 Dec at 07:00 pm Winchester Moose Lodge 1283 ENTERTAINMENT
KIDS NIGHT OUT "Holiday Themed" AGES 6-12 at Easely Created Fri, 11 Dec at 05:30 pm Easely Created Winchester KIDS
Weekly SINGO Music Bingo Nights at Bright Box - Winchester Fri, 22 Aug at 06:30 pm Bright Box Theater FREE BINGO
Local Boy Timmy @ Winchester Virginia Eagles Club 824 Fri, 30 Oct at 07:00 pm Eagle's Club Aerie #824 PERFORMANCES
Chick-fil-a Class of 2027 SPIRIT NIGHT! Tue, 13 Oct at 05:00 pm Chick-fil-A Rutherford Crossing (Winchester, VA) WORKSHOPS
Winchester, Frederick, Clarke Republican Women Christmas Lunch Wed, 09 Dec at 11:30 am Village Square Restaurant USD 29 CHRISTMAS