Trunk or Treat on Loudoun Street Sat, 17 Oct at 02:30 pm 302 S Loudoun Street, Winchester, VA HALLOWEEN
Apple Harvest Festival Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
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
Fall Fun after dark at West Oaks! Fri, 09 Oct 4305 Middle Road, Winchester, VA, United States, Virginia 22602 MUSIC
Pete Evick's Retro Rock Revival Sat, 10 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 ENTERTAINMENT
The YDC's 2026 Festival of Trees Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA FESTIVALS
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
Sun Dogs: A Tribute to RUSH Sat, 17 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 MUSIC
Emo Night Karaoke 11/7 @ Bright Box Theater Sat, 07 Nov at 07:00 pm Bright Box Theater USD 20 KARAOKE
MURDER MYSTERY Paint Night "The Ravens Secret" at Easely Created Sat, 10 Oct at 05:00 pm Easely Created Winchester DRAWING-PAINTING
JILL FULTON BAND @ PICCADILLY'S Sat, 10 Oct at 07:30 pm Piccadilly's Public House and Restaurant MUSIC
James & Joel Tribute Returns to Brightbox Winchester Sun, 25 Oct at 06:00 pm The Bright Center in Old Town Winchester MUSIC
A Diva's Halloween Special Benefiting Winchester's First LGBTQ Center Sat, 24 Oct at 07:00 pm Bright Box Theater HEALTH-WELLNESS
Odie and The Country Band at the Winchester Moose #1283 Fri, 23 Oct at 07:00 pm Winchester Moose Lodge 1283 MUSIC
Dancing with the Goats at Peaceful Fields Sanctuary! Sat, 07 Nov at 03:00 pm Peaceful Fields Sanctuary USD 17 FITNESS
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 MUSIC
Leadership: Most People Don't Fri, 23 Oct at 08:30 am The Green House Of Old Town USD 54 TO 249 BUSINESS
Faith, Love and Laughter - A Country Christmas Sat, 05 Dec at 06:00 pm 252 Costello Drive Winchester Va. 22602 ENTERTAINMENT
Joey Harkum (Love & Labor 10 Year Anniversary Celebration) w/ Ray Wroten Fri, 13 Nov at 08:00 pm Bright Box Theater FRIDAY-THE-13TH
Katie's Country Music Fest Sat, 14 Nov at 08:00 pm Backseat Events USD 39 TO 135 COUNTRY-MUSIC-FESTIVALS
God Blessed Winchester - Little Texas at Backseat! Fri, 13 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 MUSIC
Winchester Moose #1283 presents Odie and The Country Band Sat, 05 Dec at 07:00 pm Winchester Moose Lodge 1283 ENTERTAINMENT
Homestead Harvest Festival Sat, 24 Oct at 05:00 am 2502 N Frederick Pike, Winchester, VA 22603-4162, United States FESTIVALS
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
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