Festivals in Winchester

Check out happening festivals events all around Winchester, VA

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

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

Sunflower Festival

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

Samhain Market & Zombie Walk

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

Gardens at Night: Oh Blackwater & Space Cowboy

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

Wings and Wheels - Winchester, VA

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

Fiddles & Fifths 2025

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

West Oaks Apple Harvest Festival!

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

Harvest Hoedown

 Sat, 27 Sep at 05:00 pm Landfall Lodge

September Full Moon Night: Corn Moon

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

Farm & Maker’s Saturday Market

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

Harvest Market @ WBW

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

Oktoberfest @ WBW

 Sat, 20 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

Backseat's Haunted Metal Bash

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

Trunk or Treat on Loudoun Street!

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

A Christmas Carol

 Thu, 06 Nov Winchester Little Theatre

2025 Addicted To Hope Rally

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

Spring Arbor Cruise In

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

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Celebracion of Winchester

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

Blessing of the Harvest

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

Mabon Harvest Market

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

Latin Festival Fundraiser

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

Samhain Luna Market 2025

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

SPAR Septempurr Vendor Fair

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

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

First Friday

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

3rd Annual Alumni Picnic!

 Sat, 13 Sep at 12:00 pm Kiwanis Club II Pavilion | 812 Oak Drive , Winchester, VA 22601

Cash Party

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

West Oaks Fall Harvest Festival!

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

The Faire at Canterbury

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

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

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

How-to Day

 Sat, 27 Sep at 10:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

2025 Winchester Medical Center NICU Reunion

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

The Lowdown Drifters at The Monument

 Sun, 05 Oct at 07:00 pm The Monument

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

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

3rd Annual Winchester Zombie Walk

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

Trainwreck LIVE at WOFM Fall Festival

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

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

MSV at Night: The Lua Project

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

Winchester Moose NYE Celebration - Tuff Luck Band

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

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

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

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