Upcoming Christmas Carols Events

Winchester Winter Village

 Old Town Winchester Walking Mall 6 Dec 2025
KIDS

A Christmas Carol at Winchester Little Theatre Inc.

 Winchester Little Theatre Inc. 7 Nov 2025
ART

A Christmas Carol

 Winchester Little Theatre 6 Nov 2025
CHRISTMAS-CAROLS

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Upcoming Food & Drinks Events

Victory Christmas Bazaar

 2870 Middle Road, Winchester, VA 22 Nov 2025
CHRISTMAS

NAACP Chili Cookoff & Competition

Winchester Brew Works 22 Nov 2025
CONTESTS

Christmas Maker’s Market

2502 N. Frederick Pike, Winchester, VA 6 Dec 2025
HOLIDAY

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Upcoming Thanksgiving Events

Library Shop Sale @ Handley Library

 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 29 Nov 2025
NONPROFIT

Voltage Wrestling presents: The Rumble, Rush, Rampage

 Backseat Events 29 Nov 2025
SPORTS

The Psychedelic Sounds of The Robbie Limon Band

 Bright Box Theater 26 Nov 2025
MUSIC

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Upcoming Christmas Markets & Fairs Events

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 2025
CHRISTMAS

Yuletide Mystical Market

 Raven Conjure 14 Dec 2025
HOLIDAY

Holiday Market & Big Schloss Release Day!

 320 N Cameron St, Winchester, VA 29 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

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Upcoming New Year Events

December Full Moon Night: Cold Moon

 125 S. Loudoun Street, Winchester, VA 4 Dec 2025

Chuggalug at our fav Winchester Elks!

 Fraternal Order of Elks Lodge 867 3 Jan 2026

Blues, Brass & Bubbly: A New Year’s Eve with Terry Oates & The Mudcats

 114 Full House Drive, Winchester, VA 31 Dec 2025
NEW-YEAR

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Upcoming Pop-Ups Events

Windependent Weekend

 Old Town Winchester Walking Mall 28 Nov 2025
SHOPPING

Sidney Pop-Up Market

 603 S. Loudoun Street, Winchester, VA, United States, Virginia 22601 29 Nov 2025
POP-UPS

Artisan/Vendor Holiday Pop-Up Market at Easely Created

 Easely Created Winchester 28 Nov 2025
POP-UPS

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Upcoming Festivals Events

Beltane Luna Market 2026

 125 S. Loudoun Street, Winchester, VA 9 May 2026
FESTIVALS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 6 Dec 2025
FESTIVALS

Cash Party

 250 Costello Dr, Winchester, VA 22602-4310, United States 24 Jan 2026
PARTIES

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Upcoming Live Music Events

Chelsea Cushman, mezzo-soprano & Maja Tremiszewska, piano

 Goodson Chapel Recital Hall 5 Dec 2025
ART

Byron Jones, baritone & Karen Walker, piano

 Goodson Chapel Recital Hall 24 Nov 2025
MUSIC

Legacy Christian Academy Christmas Concert

 Daniel Morgan Middle School 16 Dec 2025
MUSIC FREE

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Trending Events in Winchester

2025 City of Winchester Old Town Holiday Parade with Winchester Corgis

City of Winchester VA - Local Government 1 Dec 2025
CHRISTMAS-PARADES

Sip & Sourdough Workshop

 Valerie Hill Vineyard & Winery 22 Nov 2025
WORKSHOPS

Yule Luna Market 2025

 125 S. Loudoun Street, Winchester, VA 29 Nov 2025
HOLIDAY

Solenberger’s Hardware LOVE THE LOCALS

 832 Berryville Ave, Winchester, VA 22 Nov 2025
ART

Drag bingo at 5050 taphouse

5050Taphouse 21 Nov 2025
BINGO

Holiday Wreath Making Workshop

 The Homestead Farm at Fruit Hill Orchard LLC 13 Dec 2025
WORKSHOPS USD 66

Karaoke Night with Route 11 DJ

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 21 Nov 2025
KARAOKE

Holiday Bazaar

164 Poorhouse Rd, Winchester, VA 22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

A Christmas Carol at Winchester Little Theatre

 Winchester Little Theatre 28 Nov 2025
CHRISTMAS

Cazhmiere @ Backseat Event Center w/Souled Out!

 Backseat Events 5 Dec 2025
ENTERTAINMENT

Vino Art Club - November

 127 S. Braddock St., Winchester, VA 21 Nov 2025
ART

Pink Friday Boutique Crawl

 Old Town Winchester Walking Mall 21 Nov 2025
BLACK-FRIDAY

Clay Gingerbread House

157 N Loudoun St, Winchester, VA, United States, Virginia 22601 21 Nov 2025
WORKSHOPS

Flute Ensemble

 Goodson Chapel Recital Hall 13 Dec 2025
CONCERTS

Follow The Star 2025 - Live Nativity Walking Tour

 Fellowship Bible Church 6 Dec 2025
CHRISTMAS

More things to do in Winchester

Christmas Carols
Food & Drinks
Thanksgiving
Christmas Markets & Fairs
New Year
Pop-Ups
Festivals
Live Music
Christmas Parades
Halloween
Christmas Wreath Workshops
Parades
Comedy
Christmas Light Displays
Carnivals
Bar Crawls