Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Nitty Gritty Dirt Band at The Monument

 Sun, 07 Jun at 07:30 pm The Monument

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Bryan Martin in Winchester

 Thu, 28 May at 08:00 pm Backseat Events

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

KidzFest

 Sat, 13 Jun at 12:00 pm Old Town Winchester Walking Mall

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Strawberry Festival

 Sat, 23 May at 05:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 4305 Middle Rd, Winchester, VA 22602, United States

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Apple Harvest Festival

 Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

VIP Meet and Greet (General Admission Sold Separately)

 Thu, 04 Jun at 08:00 pm Backseat Events USA USD 82

First Friday

 Fri, 05 Jun at 05:00 pm Old Town Winchester

VA250 Fireworks Celebration

 Sat, 11 Jul at 08:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Peaches & Beaches Festival

Sat, 01 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Homestead Harvest Festival

Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

80s Prom Rescue Fundraiser

 Sat, 30 May at 07:00 pm Backseat Events

Friday Night West Oaks Farm Concert! Souled Out

 Fri, 19 Jun at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Dawg Days of Summer: Hot Dog Crawl

 Sat, 22 Aug at 12:00 pm Old Town Winchester USD 34

Friday Night West Oaks Farm Concert! Chris Darlington Band

 Fri, 21 Aug at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

America 250th Celebration Elks 867

 Fri, 03 Jul at 07:00 pm Fraternal Order of Elks Lodge 867

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Corks & Cakes

 Sat, 20 Jun at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Lebanese Wine Pairing Dinner at Byblos Winchester

 Sun, 12 Jul at 06:00 pm Byblos Winchester USD 77 to 87

Friday Night West Oaks Farm Concert! CAZHMIERE

 Fri, 18 Sep at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Winchester, VA @ Bright Box Theater

 Fri, 31 Jul at 09:00 pm Bright Box Theater

Fall Harvest Festival

Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

2026 Third Winchester Battlefield 5k/10k/Half

 Sat, 08 Aug at 07:30 am 251 First Woods Dr, Winchester, VA 22603-5800, United States

Emo Night Karaoke 7/25 @ Bright Box Theater

 Sat, 25 Jul at 07:00 pm Bright Box Theater USD 20

Comedy to the Rescue

 Tue, 23 Jun at 05:30 pm 15 N Loudoun St, Winchester, VA 22601-4715, United States

Bryan Martin at Backseat Events

 Thu, 28 May Backseat Events

Live Music with Rachel Brinkmeier

 Sat, 23 May at 03:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Tea Party Treats

 Sat, 23 May at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Bluegrass on the Farm

 Thu, 11 Jun at 06:00 pm 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

The Eagles Club 824 presents Odie and The Country Band (members and invited guests only)

 Fri, 03 Jul at 07:00 pm Winchester Virginia Eagles Club 824

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

 Fri, 14 Nov at 08:00 pm Escutcheon Brewing Co. USD 13

Open Music Jam on the Farm, Phelpsmore Lane

 Fri, 07 Aug at 06:00 pm 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

11 Principals that Separate Good Leaders from Exceptional CEO's

 Fri, 09 Jan at 08:30 am Winchester Regional Airport (OKV) Free

Winchester Elks Lodge

 Sat, 22 Aug at 07:00 pm Fraternal Order of Elks Lodge 867

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

 Fri, 22 Aug at 06:30 pm Bright Box Theater Free

MoveMentation's FUN-raiser

 Sat, 11 Jul at 05:00 pm 740 Merrimans Ln, Winchester, VA 22601, United States