Take a Back Road to Backseat: Rodney Atkins LIVE! Sat, 24 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 COUNTRY-MUSIC-FESTIVALS
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
Old Town Winchester Ghost Tales Walking Tour Sat, 24 Oct at 07:30 pm Shenandoah Valley Civil War Museum ART
Pumpkin Festival Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
Fall Harvest Festival Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 HARVEST-FESTIVAL
Farm-to-Table Harvest Dinner with Chef Brandon Milhon Sat, 17 Oct at 06:00 pm Patti's Place USD 49 TO 97 FOOD-DRINKS
2026 YES Conference (Youth Empowered for Success) Tue, 20 Oct at 09:00 am Halpin-Harrison Hall USD 39 FITNESS
SPOOKY RIDDIM HOURS - HALLOW'S EVE EDITION Fri, 30 Oct at 08:00 pm Bright Box Theater USD 13 TO 29 FITNESS
Celebrate Community Cats this Fall in Style Sun, 18 Oct at 02:00 pm The George Washington A Wyndham Grand Hotel USD 50 FITNESS
Fall Fun after dark at West Oaks! Fri, 09 Oct 4305 Middle Road, Winchester, VA, United States, Virginia 22602 MUSIC
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
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
Spooktacular Scavenger Hunt For Charity Sat, 24 Oct at 04:00 pm Winchester Brew Works USD 17 TO 30 FITNESS
Bright Box Theater | THUNDERSTRUCK W/ SO LOW Fri, 09 Oct at 07:00 pm Bright Box (Winchester, VA) CONCERTS
LAPTOP EVENT FOR VETERANS 10/16/26 Fri, 16 Oct at 09:00 am HIVE — Hub for Innovators, Veterans and Entrepreneurs FREE FITNESS
Emo Night Karaoke 11/7 @ Bright Box Theater Sat, 07 Nov at 07:00 pm Bright Box Theater USD 20 KARAOKE
Colby T. Helms & The Virginia Creepers w/ Brennan Edwards Fri, 23 Oct at 08:00 pm Bright Box Theater MUSIC
Swing Into Giving Fundraiser Dance with a Live Swing Band! Fri, 09 Oct at 06:00 pm Braddock Street United Methodist Church NONPROFIT
Concern Hotline's 6th Annual Boo Kees Memorial Golf Tournament Fri, 09 Oct at 09:00 am Rock Harbor Golf Course SPORTS
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
MJ The Illusion - The Michael Jackson Experience Thu, 22 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 CONCERTS
251st USMC Ball Sat, 14 Nov at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 NONPROFIT
James & Joel Tribute Returns to Brightbox Winchester Sun, 25 Oct at 06:00 pm The Bright Center in Old Town Winchester MUSIC
"Halloween Whodunit 3" - A Murder Mystery Show 10PM Sat, 17 Oct at 10:00 pm Bright Box Theater ENTERTAINMENT
KIDS NIGHT OUT "SPOOKY HOUSE" AGES 6-12 at Easely Created Fri, 23 Oct at 05:30 pm Easely Created Winchester KIDS
Backseat Halloween Bash with Davisson Brothers Band Sat, 31 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 MUSIC
Fire and Rescue 5K Sat, 10 Oct at 08:00 am Village Square Restaurant and V2 Oyster Bar & Lounge SPORTS
Spooky Fun 2026 Fri, 16 Oct at 05:30 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601 HALLOWEEN
A Diva's Halloween Special Benefiting Winchester's First LGBTQ Center Sat, 24 Oct at 07:00 pm Bright Box Theater HEALTH-WELLNESS
Bluegrass on the Farm Thu, 15 Oct at 06:00 pm 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 MUSIC
THE HAUNT | Halloween Bass Takeover @ Blue Fox Sat, 24 Oct at 07:00 pm 1160 Millwood pike Winchester va MUSIC
Odie and The Country Band at the Winchester Moose #1283 Fri, 23 Oct at 07:00 pm Winchester Moose Lodge 1283 MUSIC
Orchard View Elementary Nest Fest! A Benefit Concert for Frederick County Families in Need Fri, 09 Oct at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602 MUSIC
CD’s 10th Annual Car Show & $5 Propane fill-up Sat, 10 Oct at 09:00 am 2951 Northwestern Pike Winchester Va 23603, Winchester, VA CAR-SHOWS
Shepherd of the Hills Trunk or Treat Sat, 17 Oct at 12:00 pm 200 Sulky Dr (Near Alamo Theater), Winchester, VA, United States, Virginia 22602 NONPROFIT
Nest Fest - Student and Families in Need Benefit Concert Fri, 09 Oct at 05:00 pm 4275 Middle Rd, Winchester, VA, United States, Virginia 22602 MUSIC
Dancing with the Goats at Peaceful Fields Sanctuary! Sat, 07 Nov at 03:00 pm Peaceful Fields Sanctuary USD 17 FITNESS
Winchester - Virginia Concealed Carry Class - $55 Sun, 25 Oct at 11:00 am Sportsman's Warehouse (Winchester, VA) WORKSHOPS
Women Entrepreneurs Coffee Networking Event Wed, 23 Sep HIVE — Hub for Innovators, Veterans and Entrepreneurs FREE FITNESS
2026 Winchester Local CE Tue, 13 Oct at 06:00 pm The George Washington A Wyndham Grand Hotel (Garden Room) USD 25 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
West Oaks Small Business Saturday Holiday Craft Show 2026 Sat, 28 Nov at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602
Sip and Paint "Vintage Christmas Tree" Bisque Workshop AT Easely Created Sat, 21 Nov at 05:00 pm Easely Created Winchester WORKSHOPS
Hell Yeah! Montgomery Gentry featuring Eddie Montgomery LIVE Fri, 06 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603 COUNTRY-MUSIC-FESTIVALS
Sip & Paint Couples and Solo Painters Paint Night AT Easely Created Sat, 24 Oct at 05:00 pm Easely Created Winchester WORKSHOPS
2026 Trunk or Treat & Fall Festival Wed, 21 Oct at 06:00 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 FESTIVALS
Art Again Trash Bash @ Hideaway Cafe Sat, 24 Oct at 05:00 pm 141 S Loudoun St, Winchester, VA 22601-4717, United States ART
Leadership: Most People Don't Fri, 23 Oct at 08:30 am The Green House Of Old Town USD 54 TO 249 BUSINESS
Free Fall Festival and Trunk or Treat Sun, 25 Oct at 01:00 pm 181 Nazarene Dr, Winchester, VA, United States, Virginia 22601 FESTIVALS
SAVE THE DATE DIY Wooden Barn Quilt Class at Easely Created Sat, 10 Oct at 02:00 pm Easely Created Winchester WORKSHOPS
WILD ADVENTURES: A Smart Zoo Experience in WINCHESTER - Sunday (10/11)!!! Sun, 11 Oct at 12:00 pm Lowe's Home Improvement (2200 S. Pleasant Valley Road, ) KIDS
Faith, Love and Laughter - A Country Christmas Sat, 05 Dec at 06:00 pm 252 Costello Drive Winchester Va. 22602 ENTERTAINMENT