Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Wings and Wheels - Winchester, VA

 Sat, 18 Oct at 10:00 am Winchester Regional Airport - OKV

West Oaks Apple Harvest Festival!

 Sun, 05 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Samhain Market & Zombie Walk

 Sun, 12 Oct at 11:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

Trunk or Treat on Loudoun Street!

 Sat, 18 Oct at 06:00 pm 302 S Loudoun Street, Winchester, VA

Native Plant Festival

 Sat, 04 Oct at 10:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Backseat's Haunted Metal Bash

 Fri, 31 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Farm & Maker’s Saturday Market

Sat, 25 Oct at 10:00 am 2502 N. Frederick Pike, Winchester, VA

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Samhain Luna Market 2025

 Sat, 11 Oct at 10:00 am 125 S. Loudoun Street, Winchester, VA

2025 Winchester Medical Center NICU Reunion

 Sun, 12 Oct at 01:00 pm West Oaks Farm Market

West Oaks Fall Harvest Festival!

 Sun, 19 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

"It Don't Mean a Thing" Swing Dance with the Silver Tones Swing Band

 Sat, 01 Nov at 06:30 pm Brandt Student Center

Guest Reading: Readings with Rachel

Sat, 25 Oct at 11:00 am 125 S. Loudoun Street, Winchester, VA

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

Fall Fest

 Wed, 29 Oct at 07:00 pm 2870 Middle Rd, Winchester, VA, United States, Virginia 22601

The Lowdown Drifters at The Monument

 Sun, 05 Oct at 07:00 pm The Monument

Guest Reading: Kindred Roots Tarot

Sat, 15 Nov at 11:00 am 125 S. Loudoun Street, Winchester, VA

2025 Trunk or Treat & Fall Festival

 Wed, 22 Oct at 06:30 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Guest Reading: Kindred Roots Tarot

Sat, 06 Dec at 11:00 am 125 S. Loudoun Street, Winchester, VA

A Christmas Carol

 Thu, 06 Nov Winchester Little Theatre

Fall Fest 2025

 Fri, 17 Oct at 05:30 pm 2333 Roosevelt Blvd., Winchester, VA, United States, Virginia 22601

TreeFest 2025 at Jim Barnett Park

 Sat, 04 Oct at 10:00 am Jim Barnett Park

3rd Annual Winchester Zombie Walk

 Sun, 12 Oct at 02:00 pm 105 Millwood Ave, Winchester, VA, US

Halloween Ride

 Sat, 25 Oct at 01:00 pm Taylor Pavilion Winchester

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

 Fri, 07 Nov at 09:00 am 102 Montague Ave Free

Cash Party

 Sat, 24 Jan at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

Winchester Moose NYE Celebration - Tuff Luck Band

Wed, 31 Dec at 06:00 pm Winchester Moose Lodge 1283

Trainwreck LIVE at WOFM Fall Festival

 Sat, 18 Oct at 04:00 am 4305 Middle Rd, Winchester, VA 22602, United States

Trainwreck LIVE at WOFM Fall Festival

 Sun, 19 Oct at 01:00 pm West Oaks Farm Market