Winchester Festivals Events

Samhain Market & Zombie Walk

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

PICKLE-CHESTER! The West Oaks 2nd Annual Pickle Festival!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 7 Sep 2025

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 6 Sep 2025

Mediumship Faire 2025

125 S. Loudoun Street, Winchester, VA 23 Aug 2025

Wings and Wheels - Winchester, VA

Winchester Regional Airport - OKV 18 Oct 2025

Harvest Hoedown

Landfall Lodge 27 Sep 2025

Gardens at Night: Oh Blackwater & Space Cowboy

901 Amherst St, Winchester, VA, United States, Virginia 22601 12 Sep 2025

Fiddles & Fifths 2025

Shenandoah Valley Civil War Museum 13 Sep 2025

West Oaks Apple Harvest Festival!

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

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 27 Sep 2025

Farm & Maker’s Saturday Market

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

Phelpsmore LANE Stone Soup Gathering

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 4 Sep 2025

JWHS FFA Car Show- Fast and Furious Autos

161 Apple Pie Ridge Road, Winchester, VA, United States, Virginia 22603 6 Sep 2025

Oktoberfest @ WBW

320 N Cameron St, Winchester, VA 20 Sep 2025

A Christmas Carol

Winchester Little Theatre 6 Nov 2025

2025 Addicted To Hope Rally

Valley Heath Cancer Center 6 Sep 2025

" Let It Begin Tour"

Backseat Events 9 Oct 2025

Bones Owen at The Monument

The Monument 30 Aug 2025

September Full Moon Night: Corn Moon

125 S. Loudoun Street, Winchester, VA 7 Sep 2025

Blessing of the Harvest

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 13 Sep 2025

Harvest Market @ WBW

320 N Cameron St, Winchester, VA 27 Sep 2025

Trunk or Treat on Loudoun Street!

302 S Loudoun Street, Winchester, VA 18 Oct 2025

Celebracion of Winchester

Taylor Pavilion Winchester 20 Sep 2025

ShenArts Fest

Old Town Winchester Walking Mall 6 Sep 2025

Mx. Winchester Pride Pageant 2025

Bright Box Theater 30 Aug 2025

Mabon Luna Market 2025

125 S. Loudoun Street, Winchester, VA 20 Sep 2025

Samhain Luna Market 2025

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

Latin Festival Fundraiser

Braddock Street United Methodist Church 20 Sep 2025

15th Annual Patsy Cline Block Party

608 South Kent Street, Winchester, VA, United States, Virginia 22601 30 Aug 2025

Dancing Thru the Decades

Backseat Events 7 Feb 2026

Spring Arbor Cruise In

2093 Northwestern Pike, Winchester, VA, United States, Virginia 22603 7 Sep 2025

First Friday

Old Town Winchester Walking Mall 3 Oct 2025

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

Brandt Student Center 1 Nov 2025

Rally on Valley

2818 Valley Avenue, Winchester, VA 23 Aug 2025

R.A.M.P Fest! @Jim Barnett Skate Park

Jim Barnett Park 30 Aug 2025

Backseat's Haunted Metal Bash

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

SPAR Septempurr Vendor Fair

Solenberger's True Value Hardware 14 Sep 2025

West Oaks Fall Harvest Festival!

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

VBS at What's New Worship

2249 Valor Dr, Winchester, VA, United States, Virginia 22601 30 Aug 2025

3rd Annual Alumni Picnic!

Kiwanis Club II Pavilion | 812 Oak Drive , Winchester, VA 22601 13 Sep 2025

The Faire at Canterbury

300 Westminster Canterbury Drive, Winchester, VA, United States, Virginia 22603 20 Sep 2025

Mabon Harvest Market

105 Millwood Ave, Winchester, VA 21 Sep 2025

2025 Winchester Medical Center NICU Reunion

West Oaks Farm Market 12 Oct 2025

The Lowdown Drifters at The Monument

The Monument 5 Oct 2025

2025 Doodle Romp

Briedé Family Vineyards 25 Oct 2025

MSV at Night: The Lua Project

901 Amherst St, Winchester, VA, United States, Virginia 22601 26 Sep 2025

3rd Annual Winchester Zombie Walk

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

Texas Hippie Coalition

Backseat Events 16 Oct 2025

Winchester Moose NYE Celebration - Tuff Luck Band

Winchester Moose Family Center 1283 31 Dec 2025

PICKLECHESTER! Dill Pickers at West Oaks Farm Market Sunday, September 7, 2025

West Oaks Farm Market 7 Sep 2025

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

102 Montague Ave 7 Nov 2025

Saving Abel

Backseat Events 15 Oct 2025

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 19 Oct 2025

Volunteer Fair - Community Connect and Serve

399 Apple Pie Ridge Rd, Winchester, VA 22603-4311, United States 25 Sep 2025

Hungry for History

Winchester-Frederick County Convention & Visitors Bureau 23 Aug 2025