Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Farm Concert - Souled Out at West Oaks!

 Fri, 19 Sep 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

End Of Summer Bash Drag Show!

 Sat, 30 Aug at 08:00 pm 320 N Cameron St, Winchester, VA, United States, Virginia 22601 USD 13 to 23

Mediumship Faire 2025

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

Sunflower Festival

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

Wings and Wheels - Winchester, VA

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

Farm & Maker’s Saturday Market

Sat, 30 Aug at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Harvest Hoedown

 Sat, 27 Sep at 05:00 pm Landfall Lodge

Gardens at Night: Oh Blackwater & Space Cowboy

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

Winchester Moose Lodge 1283

 Sat, 06 Sep at 07:00 pm 215 E Cork St, Winchester, VA 22601

Fiddles & Fifths 2025

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

Bottle Shock Live!

 Fri, 22 Aug at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

NAACP Winchester Area Freedom Fund Gala Fundraiser

Sat, 20 Sep at 06:00 pm SU, Ferrari Room, 703 University Drive, Winchester VA

West Oaks Apple Harvest Festival!

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

Melanie Pearl Live at Valerie Hill

 Fri, 22 Aug at 06:00 pm Valerie Hill Vineyard & Winery

Conservation Easements: Stories, Process, Possibilities

 Thu, 11 Sep at 06:00 pm Landfall Lodge Free

Family Fossil Talk: Digging Into Dinosaurs

 Sat, 23 Aug at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Farm & Maker’s Saturday Market

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

Men’s Healthcare Forum ❣️ Hosted by NAACP Health Committee

Sat, 06 Sep at 09:00 am 1810 Roberts Street, Winchester, VA 22601

Farm & Maker’s Saturday Market

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

Type O Negative tribute - Blue Fox Billiards - Sat Sept 20

 Sat, 20 Sep at 07:00 pm Blue Fox Billiards, Bar and Grill

8ball Chip Tournament

 Sat, 30 Aug at 07:00 pm 109 Fullhouse Dr, Winchester, Va, 22603

Phelpsmore LANE Stone Soup Gathering

 Thu, 04 Sep at 11:00 am 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

FLW BACK LIVE at PICCADILLY'S!

 Fri, 29 Aug at 07:30 pm Piccadilly's Public House and Restaurant

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

Yuletide Mystical Market

 Sun, 07 Dec at 11:00 am Raven Conjure

Aaron Tippin - Stand for America at Backseat Events!

 Sat, 08 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

An Evening of Magic with David Anthony - 7PM

 Fri, 12 Sep at 07:00 pm Bright Box Theater

90s Throwback Party ft. DJ OPHIE

 Sat, 06 Sep at 09:00 pm Bright Box Theater

Oktoberfest @ WBW

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

Rodeo Disco Night- Vibrissa Winchester

 Fri, 19 Sep at 07:00 pm Vibrissa Beer (Winchester, VA)

Marvelous Macaron

 Sat, 23 Aug at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Smash & Build

Sat, 23 Aug at 10:00 am 314 Hope Dr, Winchester, VA 22601-6800, United States

Karaoke

 Fri, 22 Aug at 07:00 pm Winchester Elks Lodge

Holiday Market & Big Schloss Release Day!

 Sat, 29 Nov at 02:00 pm 320 N Cameron St, Winchester, VA

Home Food Preservation

 Thu, 28 Aug at 06:00 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

A Christmas Carol

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

Caleb Michael Gordon Group

 Sat, 18 Oct at 07:30 pm 28 W Hart St, Winchester, VA 22601-4513, United States

Weekly Beer Tasting at Shawnee Springs Market, Senseny Road

 Fri, 22 Aug at 04:00 pm Shawnee Springs Market & Cannery (Winchester, VA)

Sancerre Night With Bruce At The Beer & Wine Depot!

Fri, 22 Aug at 04:00 pm 1863 - A Berryville Pike, Winchester, VA

Graham Taylor OPC-WATTS Concert & Meal Fundraiser

 Sat, 20 Sep at 05:00 pm 217 Opequon Church Ln, Winchester, VA, United States, Virginia 22602

Family First Friday - Building Block Night

 Fri, 05 Sep at 05:00 pm 1850 Apple Blossom Dr

2025 Addicted To Hope Rally

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

Twinkle Tai Chi

Fri, 22 Aug at 07:30 pm Willow Grove

Mx. Winchester Pride 2025 Pageant

 Sat, 30 Aug at 06:00 pm Bright Box Theater

Karaoke Night with Route 11 DJ

 Fri, 26 Sep at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Live Music with Nate Hadley

 Sat, 23 Aug at 03:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Rack 'Em Billiards 10Ball

 Sat, 23 Aug at 09:00 am 109 Full House Dr, Winchester, VA 22603-4671, United States

Aug Guided Tour of Peaceful Fields Sanctuary

 Sun, 24 Aug at 02:00 pm Peaceful Fields Sanctuary USD 8

Live Music with Twisted Roots

 Sat, 23 Aug at 03:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Lyndsie Nicholson Live!

 Sat, 30 Aug at 01:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Quotable Movie Night

Thu, 28 Aug at 07:30 pm 14 W Boscawen St, Winchester, VA

The Faire at Canterbury

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

Low Water Bridge Band & Jake Kohn – Co‑Headline Hometown Show

 Sat, 04 Oct at 08:00 pm 186 North Loudoun Street, Winchester, VA

Legion Imperialis: Titan Clash

 Sat, 23 Aug at 12:00 pm 255 Market Street, Winchester, VA, United States, Virginia 22603

Winchester Elks Lodge

 Fri, 19 Sep at 07:00 pm 466 Front Royal Pike, Winchester, VA 22602-7315, United States

Bones Owen at The Monument

 Sat, 30 Aug at 07:00 pm The Monument

Cat Cave Crochet Circle

 Fri, 22 Aug at 02:30 pm 111 Featherbed Lane, Winchester, VA

Blessing of the Harvest

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

Tea with Martha Washington Open House

 Sun, 24 Aug at 02:00 pm 1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601

Karaoke with DJ Blue Nova

 Wed, 27 Aug at 07:00 pm 30 East Piccadilly Street, Winchester, VA, United States, Virginia 22601

Cousins Maine Lobster

 Sat, 06 Sep at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Cousins Maine Lobster at James Charles Winery (Winchester)

 Sat, 06 Sep at 12:00 pm 4063 Middle Rd, Winchester, VA 22602

Terrarium Workshop

 Sat, 13 Sep at 11:00 am Weber's Nursery & Garden Center

Trivia @ DCBC: All Things NFL

 Wed, 03 Sep at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

J&J Entertainment presents: Northeast Groovers live @ Backseat Events

 Fri, 22 Aug at 08:00 pm Backseat Events

Improv Comedy with Porkchop Volcano - Bright Box

 Fri, 05 Sep at 07:00 pm Bright Box Theater

Harvest Market @ WBW

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

Succulent Bowl Workshop

 Sat, 20 Sep at 11:00 am Weber's Nursery & Garden Center

Gray Matter @Winchester Moose

 Sat, 25 Oct at 07:00 pm Winchester Moose Lodge 1283

First Friday

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

Winchester Meadow Makers

 Sun, 24 Aug at 01:00 pm Jim Barnett Park

I Scream, You Scream, We All Scream for Ice Cream

 Fri, 29 Aug at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Kelly Bell Band LIVE at Bright Box

 Fri, 22 Aug at 08:00 pm Bright Box Theater

Airmont Road @ Backseat Bar & Grill

 Sat, 01 Nov at 08:30 pm Backseat Bar and Grill

Sept Volunteer Day at Peaceful Fields Sanctuary

 Sun, 07 Sep at 10:00 am Peaceful Fields Sanctuary

Celebracion of Winchester

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

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

 Sat, 04 Oct at 08:00 pm 114 Full House Drive, Winchester, VA

Micky & The Motorcars

 Sat, 04 Oct at 07:00 pm Bright Box Theater

BikeWalk Open Meeting

 Tue, 02 Sep at 06:30 pm Handley Regional Library System

ShenArts Fest

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

I Know Medicare: Paint & Sip

 Fri, 29 Aug at 10:00 am 1169 Berryville Ave Free

Hungry for History: Valerie Hill

 Fri, 29 Aug at 07:00 pm Valerie Hill Vineyard & Winery

Shenandoah Stampalooza 2025

 Fri, 26 Sep at 03:00 pm Holiday Inn Winchester SE-Historic Gateway by IHG

Last Taste of Summer

 Sat, 23 Aug at 04:00 pm Patti's Place USD 50

A Day in the Kitchen: French Pastries

 Sat, 04 Oct at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

RUSTED BLUE @ WINCHESTER FAMILY MOOSE

Sat, 23 Aug at 07:00 pm Winchester Moose Lodge.

1st Annual Charles W. Washington, Sr. Memorial Car Show

 Sat, 23 Aug at 09:00 am 1001 E Cork St, Winchester, VA 22601-5575, United States

YDC Art Classes

 Sat, 13 Sep at 10:00 am 302 S Loudoun Street, Winchester, VA, United States, Virginia 22601

An Evening with the Kelly Bell Band

 Fri, 22 Aug at 08:00 pm Bright Box Theater

Trunk or Treat on Loudoun Street!

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

Book Club

 Mon, 25 Aug at 06:30 pm Winchester 1st Church of the Nazarene

Raise Up Parenting Conference

 Sat, 13 Sep at 09:00 am 2870 Middle Rd, Winchester, VA, United States, Virginia 22601

Ambrogi Acres 420 Game Nights 🟢

 Fri, 22 Aug at 06:00 pm 187 Chickadee Lane, 22603

2nd Annual Gala and Silent Auction

 Sat, 08 Nov at 05:30 pm West Oaks Farm Market

Petco Day at the WASPCA

 Sat, 20 Sep at 10:00 am 111 Featherbed Lane, Winchester, VA

Live Loud: Kickin’ Valentina + Bad Marriage

 Sat, 13 Sep at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

"The Answer is Murder!" - A Murder Mystery Comedy / Trivia Show // 7PM SHOW

 Sat, 23 Aug at 07:00 pm Bright Box Theater
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