Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Farm Concert - CAZHMIERE at West Oaks!

 Fri, 15 Aug at 07:00 pm 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

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

 Sun, 07 Sep at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

West Oaks Apple Harvest Festival!

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

Gardens at Night: Oh Blackwater & Space Cowboy

 Fri, 12 Sep at 07:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Mediumship Faire 2025

Sat, 23 Aug at 11:00 am 125 S. Loudoun Street, Winchester, VA

Harvest Hoedown

 Sat, 27 Sep at 05:00 pm Landfall Lodge

Fiddles & Fifths 2025

 Sat, 13 Sep at 01:00 pm Shenandoah Valley Civil War Museum

Bones Owen at The Monument

 Sat, 30 Aug The Monument

2025 Winchester Greek Festival

Sat, 16 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

Wings and Wheels - Winchester, VA

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

JWHS FFA Car Show- Fast and Furious Autos

 Sat, 06 Sep at 09:00 am 161 Apple Pie Ridge Road, Winchester, VA, United States, Virginia 22603

A Christmas Carol

 Thu, 06 Nov at 07:00 pm Winchester Little Theatre

Trunk or Treat on Loudoun Street!

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

Sunflower Festival

Sat, 06 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

First Friday

 Fri, 03 Oct at 05:00 pm Old Town Winchester Walking Mall

September Full Moon Night: Corn Moon

 Sun, 07 Sep at 04:00 pm 125 S. Loudoun Street, Winchester, VA

2025 Addicted To Hope Rally

 Sat, 06 Sep at 04:00 pm Valley Heath Cancer Center

Harvest Market @ WBW

 Sat, 27 Sep at 02:00 pm 320 N Cameron St, Winchester, VA

Farm & Maker’s Saturday Market

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

Dancing Thru the Decades

 Sat, 23 Aug at 06:00 pm Backseat Events

Oktoberfest @ WBW

 Sat, 20 Sep at 02:00 pm 320 N Cameron St, Winchester, VA

Latin Festival Fundraiser

 Sat, 20 Sep at 04:30 pm Braddock Street United Methodist Church

Raise a Glass for Virginia Beer Day!

 Thu, 14 Aug at 03:00 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Celebracion of Winchester

Sat, 20 Sep at 12:00 pm Taylor Pavilion Winchester

Farm & Maker’s Saturday Market

Sat, 27 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Rally on Valley

 Sat, 23 Aug at 10:00 am 2818 Valley Avenue, Winchester, VA

Samhain Luna Market 2025

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

Mabon Luna Market 2025

 Sat, 20 Sep at 10:00 am 125 S. Loudoun Street, Winchester, VA

ShenArts Fest

 Sat, 06 Sep at 10:00 am Old Town Winchester Walking Mall

Tucker's Pucker & Stoner Dogs at Yappy Hour

 Fri, 15 Aug at 03:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

15th Annual Patsy Cline Block Party

 Sat, 30 Aug at 10:00 am 608 South Kent Street, Winchester, VA, United States, Virginia 22601

Mx. Winchester Pride Pageant 2025

 Sat, 30 Aug at 07:00 pm Bright Box Theater

SPAR Septempurr Vendor Fair

 Sun, 14 Sep at 12:00 pm Solenberger's True Value Hardware

West Oaks Fall Harvest Festival!

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

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

 Sat, 30 Aug at 11:00 am Jim Barnett Park USD 10

The Faire at Canterbury

 Sat, 20 Sep at 10:00 am 300 Westminster Canterbury Drive, Winchester, VA, United States, Virginia 22603

VBS at What's New Worship

 Sat, 30 Aug at 03:00 pm 2249 Valor Dr, Winchester, VA, United States, Virginia 22601

First Responder Thank You Event

 Sun, 17 Aug at 02:00 pm 135 N Braddock St, Winchester, VA

Mabon Harvest Market

 Sun, 21 Sep at 11:00 am 105 Millwood Ave, Winchester, VA

Blessing of the Harvest

 Sat, 13 Sep at 02:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

The Lowdown Drifters at The Monument

 Sun, 05 Oct The Monument

Spring Arbor Cruise In

 Sun, 07 Sep at 03:00 pm 2093 Northwestern Pike, Winchester, VA, United States, Virginia 22603

2025 Doodle Romp

 Sat, 25 Oct at 11:00 am Briedé Family Vineyards

Winchester Moose NYE Celebration - Tuff Luck Band

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

MSV at Night: The Lua Project

 Fri, 26 Sep at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

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

 Sun, 07 Sep at 02:00 pm West Oaks Farm Market

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

🎁 2nd Annual Kids Shopping Free Event at SPCA Thrift! 🎄

 Sat, 20 Dec at 10:00 am 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

Trainwreck LIVE at WOFM Fall Festival

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

Volunteer Fair - Community Connect and Serve

Thu, 25 Sep at 06:00 pm 399 Apple Pie Ridge Rd, Winchester, VA 22603-4311, United States

Hungry for History

 Sat, 23 Aug at 09:00 am Winchester-Frederick County Convention & Visitors Bureau