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
Trunk or Treat on Loudoun Street Sat, 17 Oct at 02:30 pm 302 S Loudoun Street, Winchester, VA HALLOWEEN
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
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
Fall Harvest Festival Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 HARVEST-FESTIVAL
The YDC's 2026 Festival of Trees Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA FESTIVALS
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
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
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
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
Odie and The Country Band at the Winchester Moose #1283 Fri, 23 Oct at 07:00 pm Winchester Moose Lodge 1283 MUSIC
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
Little Ozzy: The Nation's Biggest Ozzy Tribute Sat, 28 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 MUSIC
Wichita Falls Band "Something about Sunday" Sun, 04 Oct at 03:00 pm 125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601 MUSIC
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