Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Winchester Winter Village

Sat, 06 Dec at 11:00 am Old Town Winchester Walking Mall

Victory Christmas Bazaar

Sat, 22 Nov at 08:00 am 2870 Middle Road, Winchester, VA

Winter Wonderland Christmas Market

Sat, 22 Nov at 09:00 am Millwood Station Banquet Hall

Yuletide Mystical Market

Sun, 14 Dec at 11:00 am Raven Conjure

Sip & Sourdough Workshop

Sat, 22 Nov at 04:00 pm Valerie Hill Vineyard & Winery

Yule Luna Market 2025

Sat, 29 Nov at 10:00 am 125 S. Loudoun Street, Winchester, VA

NAACP Chili Cookoff & Competition

Sat, 22 Nov at 01:00 pm Winchester Brew Works

Holiday Market & Big Schloss Release Day!

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

Solenberger’s Hardware LOVE THE LOCALS

Sat, 22 Nov at 09:00 am 832 Berryville Ave, Winchester, VA

Drag bingo at 5050 taphouse

Fri, 21 Nov at 10:00 pm 5050Taphouse

Santa Pub Crawl — Downtown Winchester, VA

Fri, 05 Dec at 05:00 pm 15 E Boscawen st, Winchester, VA

Holiday Wreath Making Workshop

Sat, 13 Dec at 01:00 pm The Homestead Farm at Fruit Hill Orchard LLC USD 66

A Christmas Carol at Winchester Little Theatre Inc.

Fri, 07 Nov at 08:00 pm Winchester Little Theatre Inc.

December Full Moon Night: Cold Moon

Thu, 04 Dec at 06:00 pm 125 S. Loudoun Street, Winchester, VA

Fire Pit Fridays

Fri, 21 Nov at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Milano's Game Night!

Wed, 19 Nov at 08:00 pm 107 W Boscawen St, Winchester, VA, United States, Virginia 22601

Karaoke Night with Route 11 DJ

Fri, 21 Nov at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Holiday Bazaar

Sat, 22 Nov at 08:00 am 164 Poorhouse Rd, Winchester, VA

A Christmas Carol

Thu, 06 Nov Winchester Little Theatre

Brotherhood of Christ | Men’s Fellowship Night.

Fri, 21 Nov at 06:30 pm 165 Miracle Way, Winchester, VA, United States, Virginia 22603

Christmas Maker’s Market

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

A Christmas Carol at Winchester Little Theatre

Fri, 28 Nov at 08:00 pm Winchester Little Theatre

Ambrogi Acres 420 Game Nights 🟢

Fri, 21 Nov at 06:00 pm 187 Chickadee Lane, 22603

Cazhmiere @ Backseat Event Center w/Souled Out!

Fri, 05 Dec at 08:00 pm Backseat Events

Chelsea Cushman, mezzo-soprano & Maja Tremiszewska, piano

Fri, 05 Dec at 07:30 pm Goodson Chapel Recital Hall

Vino Art Club - November

Fri, 21 Nov at 06:00 pm 127 S. Braddock St., Winchester, VA

Pink Friday Boutique Crawl

Fri, 21 Nov at 11:00 am Old Town Winchester Walking Mall

Melanie Pearl Live at Roma's

Fri, 21 Nov at 08:00 pm Romas Old Town

Collin Raye in Winchester

Sat, 17 Jan at 08:00 pm Backseat Events

Elijah - The Lowest Tour

Fri, 21 Nov at 07:00 pm 186 North Loudoun Street, Winchester, VA

Acoustic Soul at Piccadilly’s Public House

Fri, 21 Nov at 07:30 pm Piccadilly's Public House and Restaurant

Clay Gingerbread House

Fri, 21 Nov at 05:30 pm 157 N Loudoun St, Winchester, VA, United States, Virginia 22601

Guest Reading: Sarah with Mad Hatter Tarot

Sat, 22 Nov at 11:00 am 125 S. Loudoun Street, Winchester, VA

Flute Ensemble

Sat, 13 Dec at 07:30 pm Goodson Chapel Recital Hall

Follow The Star 2025 - Live Nativity Walking Tour

Sat, 06 Dec at 05:00 pm Fellowship Bible Church

Bright Box Feud

Sat, 22 Nov at 07:00 pm Bright Box Theater

November TalkWALK Community Walk Presented by BikeWalk & Friends of Old Town

Sat, 22 Nov at 10:00 am Taylor Pavilion Winchester

Pro Wrestling Seminar Series w/ "Brutal" Bob Evans

Sat, 29 Nov at 12:00 pm Backseat Events

Go Big and Stay Home

Sat, 13 Dec at 04:15 pm Patti's Place USD 87

A DIVA's Christmas Special

Sat, 20 Dec at 05:30 pm Bright Box (Winchester, VA)

Library Shop Sale @ Handley Library

Sat, 29 Nov at 10:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Winchester Holiday Lights Trolley Tour

Fri, 12 Dec at 08:00 pm 1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601

Beltane Luna Market 2026

Sat, 09 May at 10:00 am 125 S. Loudoun Street, Winchester, VA

Swing into the Holidays with Winchester Swing Dance

Thu, 11 Dec at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Chuggalug at our fav Winchester Elks!

Sat, 03 Jan at 07:00 pm Fraternal Order of Elks Lodge 867

Kokodama Workshop

Sat, 22 Nov at 02:00 pm 1912 Martinsburg Pike, Winchester, VA

Heavy Rigging Systems with John Burruss

Sat, 22 Nov at 08:00 am 141 Spinning Wheel Ln USD 29

SVO Holiday Market & Pictures with Santa

Sat, 29 Nov at 11:00 am 1705 Amherst St., Suite 103, Winchester, VA

Byron Jones, baritone & Karen Walker, piano

Mon, 24 Nov at 07:30 pm Goodson Chapel Recital Hall

Black Friday with Devils Smile

Fri, 28 Nov at 08:00 pm Backseat Bar & Grill

Adopt a Plush Pet Party

Sun, 23 Nov at 12:00 pm 111 Featherbed Lane, Winchester, VA, United States, Virginia 22601

SPCA Thrift Black Friday Blowout - November 28th

Fri, 28 Nov at 12:00 pm 1944 Abrams Creek Dr, Winchester, VA 22601-4485, United States

Duke Ellington's Nutcracker

Thu, 04 Dec at 07:00 pm Bright Box Theater

Handley Library Tour - Behind the Scenes

Sat, 13 Dec at 11:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

CONTEMPO Ensembles

Thu, 04 Dec at 07:30 pm Armstrong Concert Hall

Big Hair, Bright Lights & Spank the 80s!

Fri, 19 Dec at 08:00 pm 114 Full House Drive, Winchester, VA

Transgender Day of Remembrance

Thu, 20 Nov at 06:00 pm Shenandoah University

2025 Winchester Wreaths Across America Day - Wreath Laying and Ceremony

Sat, 13 Dec at 11:00 am 401 National Ave, Winchester, VA, United States, Virginia 22602

Demyze, Shadowburn, Sad In Static @Granny's

Fri, 21 Nov at 07:00 pm Granny's Place

West Oaks Holiday Craft Show

Sat, 29 Nov at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Tinsel Tea

Sat, 06 Dec at 01:00 pm The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA USD 34 to 55

A Christmas Carol at Winchester Little Theatre

Sat, 22 Nov at 08:00 pm Winchester Little Theatre

Legacy Christian Academy Christmas Concert

Tue, 16 Dec at 06:30 pm Daniel Morgan Middle School Free

Chuck E. Cheese Spirit Night!

Fri, 21 Nov at 03:00 pm Chuck E. Cheese (145 E. Tevis St., Winchester, VA)

Monthly Volunteer Meeting

Wed, 19 Nov at 06:00 pm 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601

Voltage Wrestling presents: The Rumble, Rush, Rampage

Sat, 29 Nov at 07:30 pm Backseat Events

Tanks-Giving!

Sat, 29 Nov at 11:30 am 255 Market Street, Winchester, VA, United States, Virginia 22603

The Psychedelic Sounds of The Robbie Limon Band

Wed, 26 Nov at 07:00 pm Bright Box Theater

NW Works Chimers

Sat, 13 Dec at 02:30 pm Armstrong Concert Hall

Drinksgiving @Backseat Bar & Grill The night before Thanksgiving

Wed, 26 Nov at 07:30 pm Backseat Bar and Grill

November Monthly Meeting

Mon, 24 Nov at 07:00 pm Opequon Presbyterian Church

Messiah Sing Along

Sun, 30 Nov at 07:00 pm First Baptist Church Winchester, VA

The Nutcracker Ballet

Sat, 13 Dec at 02:00 pm John Handley High School

Emo Night Karaoke 1/23 @ Bright Box Theater

Fri, 23 Jan at 08:00 pm Bright Box Theater USD 21

Windependent Weekend

Fri, 28 Nov at 10:00 am Old Town Winchester Walking Mall

Make Mosaics with Christy Dunkle

Wed, 03 Dec at 06:00 pm Dividing Creek Beer Co USD 82

Champagne Saturday Class at Briedé Family Vineyards

Sat, 06 Dec at 12:00 pm Briedé Family Vineyards

Tasting with Misty Mountain Meadworks

Sat, 06 Dec at 12:00 pm Murphy Beverage Company

Worship Services — Winchester

Sun, 23 Nov at 10:30 am 399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603

Cocoa with Santa

Fri, 05 Dec at 04:30 pm Millbrook High School

Adventures Through Grief - Winchester Young Adult Group

Wed, 26 Nov at 05:30 pm Handley Regional Library System

Retro, Radical, and Totally Tubular: The Legwarmers Live

Sat, 22 Nov at 08:00 pm 114 Full House Drive, Winchester, VA

Backseat Winchester Va

Sat, 20 Dec at 08:00 pm Backseat Bar and Grill

Sidney Pop-Up Market

Sat, 29 Nov at 10:00 am 603 S. Loudoun Street, Winchester, VA, United States, Virginia 22601

Wait Until Dark

Thu, 15 Jan at 07:00 pm Winchester Little Theatre

🟣 Scout Spark: A Sister Scout’s Social

Sun, 07 Dec at 03:00 pm Valerie Hill Vineyard & Winery

FIST PUMP FRENZY: The Shore Comes to Bright Box

Fri, 28 Nov at 09:00 pm Bright Box Theater

Keith Harkin Trio - Winchester VA Bright Box Theater

Tue, 09 Dec at 07:30 pm Bright Box Theater

Christmas Market @ The Ivy Room

Sat, 29 Nov at 10:00 am The Ivy Room

Fall Tree Planting at Rose Hill Park

Sat, 06 Dec at 09:00 am Rose Hill Park

Breach The Silence, Sonic Disciple, 9 Realms @Granny's

Sat, 06 Dec at 07:00 pm Granny's Place

GLORIA

Sat, 22 Nov at 07:00 pm First Baptist Church Winchester, VA

Fire Pit Fridays

Fri, 19 Dec at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Worship Services — Berryville

Sun, 23 Nov at 09:00 am 399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603

Museum Store Sunday

Sun, 30 Nov at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

A Christmas Carol at Winchester Little Theatre

Sat, 29 Nov at 08:00 pm Winchester Little Theatre

Fall Youth Inline Hockey Championship Sunday

Sun, 07 Dec at 01:00 pm ToV Hockey Rink @ James Wood Middle School

NW Works Chimers Concert

Sat, 13 Dec at 02:30 pm Armstrong Concert Hall

Guest Appreciation Day 🎄🔔✨

Fri, 05 Dec at 09:00 am Mane Attraction Salon & Wellness Spa

Trans Family Affinity Group

Thu, 11 Dec at 06:00 pm 124 W Piccadilly St, Winchester, VA 22601-3916, United States

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