Winchester Festivals Events

Festivals Happening Next in Winchester, VA

Wings and Wheels - Winchester, VA

 Winchester Regional Airport - OKV 18 Oct 2025
CAR-SHOWS

Samhain Market & Zombie Walk

 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 12 Oct 2025

West Oaks Apple Harvest Festival!

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 5 Oct 2025
FESTIVALS

Trunk or Treat on Loudoun Street!

 302 S Loudoun Street, Winchester, VA 18 Oct 2025
HALLOWEEN

Native Plant Festival

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 4 Oct 2025
FESTIVALS

Backseat's Haunted Metal Bash

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 31 Oct 2025
HALLOWEEN

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 25 Oct 2025

Samhain Luna Market 2025

 125 S. Loudoun Street, Winchester, VA 11 Oct 2025
HALLOWEEN

2025 Winchester Medical Center NICU Reunion

 West Oaks Farm Market 12 Oct 2025
KARAOKE

" Let It Begin Tour"

 Backseat Events 9 Oct 2025
ART

Texas Hippie Coalition

 Backseat Events 16 Oct 2025

First Friday

 Old Town Winchester Walking Mall 3 Oct 2025
FIRST-FRIDAY

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

 Brandt Student Center 1 Nov 2025
MUSIC

Guest Reading: Readings with Rachel

125 S. Loudoun Street, Winchester, VA 25 Oct 2025
FESTIVALS

West Oaks Fall Harvest Festival!

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 19 Oct 2025
FESTIVALS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 15 Nov 2025
FESTIVALS

The Lowdown Drifters at The Monument

 The Monument 5 Oct 2025
CONTESTS

2025 Trunk or Treat & Fall Festival

 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 22 Oct 2025
TRUNK-OR-TREAT

Dancing Thru the Decades

 Backseat Events 7 Feb 2026
FESTIVALS

A Christmas Carol

 Winchester Little Theatre 6 Nov 2025
CHRISTMAS-CAROLS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 6 Dec 2025
FESTIVALS

Fall Fest 2025

 2333 Roosevelt Blvd., Winchester, VA, United States, Virginia 22601 17 Oct 2025
FESTIVALS

TreeFest 2025 at Jim Barnett Park

 Jim Barnett Park 4 Oct 2025
FESTIVALS

3rd Annual Winchester Zombie Walk

 105 Millwood Ave, Winchester, VA, US 12 Oct 2025
NONPROFIT

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

 102 Montague Ave 7 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS FREE

Halloween Ride

 Taylor Pavilion Winchester 25 Oct 2025
HALLOWEEN

Cash Party

 250 Costello Dr, Winchester, VA 22602-4310, United States 24 Jan 2026
PARTIES

Saving Abel

 Backseat Events 15 Oct 2025
TRIPS-ADVENTURES

Fall Fest

 2870 Middle Rd, Winchester, VA, United States, Virginia 22601 29 Oct 2025
FESTIVALS

Winchester Moose NYE Celebration - Tuff Luck Band

Winchester Moose Lodge 1283 31 Dec 2025
MUSIC

Trainwreck LIVE at WOFM Fall Festival

 4305 Middle Rd, Winchester, VA 22602, United States 18 Oct 2025
MUSIC

Trainwreck LIVE at WOFM Fall Festival

 West Oaks Farm Market 19 Oct 2025
FESTIVALS