Upcoming Live Music Events

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

 Brandt Student Center 1 Nov 2025
MUSIC

Aaron Tippin - Stand for America at Backseat Events!

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 8 Nov 2025
MUSIC

Sin City at Backseat Bar & Grill

 Backseat Bar and Grill 15 Nov 2025

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Upcoming Festivals Events

Cheesin' for a Reason - a grilled cheese & tomato soup extravaganza

 Old Town Winchester 8 Nov 2025
FOOD-DRINKS

Guest Reading: Kindred Roots Tarot

125 S. Loudoun Street, Winchester, VA 15 Nov 2025
FESTIVALS

Guest Reading: Kindred Roots Tarot

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

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Upcoming Christmas Markets & Fairs Events

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

Victory Christmas Bazaar

 2870 Middle Road, Winchester, VA 22 Nov 2025
CHRISTMAS

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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

Winchester Moose NYE Celebration - Tuff Luck Band

Winchester Moose Lodge 1283 31 Dec 2025
NEW-YEAR

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Upcoming Pop-Ups Events

Sit. Stay. Paint!

 WASPCA Thrift Shop 6 Nov 2025
ART USD 50

Artisan/Vendor Holiday Pop-Up Market at Easely Created

 Easely Created Winchester 28 Nov 2025
POP-UPS

Sidney Pop-Up Market

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

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Upcoming Halloween Events

Backseat's Haunted Metal Bash

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 31 Oct 2025
HALLOWEEN

Halloween Special at Chick-fil-A

 Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, ) 31 Oct 2025
HALLOWEEN

Cedar Creek Grade Halloween Party

 1160 Millwood Pike, Winchester, VA, United States, Virginia 22602 1 Nov 2025
ENTERTAINMENT

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Upcoming Thanksgiving Events

Robbie Limon Band Thanksgiving Eve Party

 Bright Box Theater 26 Nov 2025
ENTERTAINMENT

A Day in the Kitchen: Thanksgiving Pies

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 22 Nov 2025
WORKSHOPS

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

 102 Montague Ave 7 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS FREE

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Upcoming Christmas Carols Events

Winchester Winter Village

 Old Town Winchester Walking Mall 6 Dec 2025
KIDS

A Christmas Carol

 Winchester Little Theatre 6 Nov 2025
CHRISTMAS-CAROLS

A Christmas Carol at Winchester Little Theatre Inc.

 Winchester Little Theatre Inc. 7 Nov 2025
ART

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Trending Events in Winchester

Monthly Full Moon Gathering - Women's Circle

 Daydream Studios 3 Nov 2025
DAY-OF-THE-DEAD USD 29

Día de Muertos

Braddock Street United Methodist Church 2 Nov 2025
MUSIC

80s Night with The Reagan Years

 186 North Loudoun Street, Winchester, VA 7 Nov 2025
ENTERTAINMENT

Harvest Pumpkin Fall Centerpiece Workshop

 The Homestead Farm at Fruit Hill Orchard LLC 1 Nov 2025
WORKSHOPS USD 82

Yule Luna Market 2025

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

2nd Annual Gala and Silent Auction

 West Oaks Farm Market 8 Nov 2025
NONPROFIT

Model Train Show and Sale

 Winchester Moose Lodge, 215 E Cork Street, Winchester, VA 8 Nov 2025
KIDS

Guest Reading: Half Tail Tarot

125 S. Loudoun Street, Winchester, VA 1 Nov 2025
WORKSHOPS

Heaven's Pit presents Brian Head Welch and Friends

 2249 Valor Dr 8 Nov 2025
ENTERTAINMENT USD 34 TO 103

Wellington 101

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 7 Nov 2025
WORKSHOPS

Shred Event - Winchester Branch

 1850 S Loudoun St, Winchester, VA 22601-4492, United States 29 Oct 2025

Breaking Breads

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 15 Nov 2025
WORKSHOPS

Veritas Fight Series- Proving Grounds

 Backseat Events 1 Nov 2025

The SideMen

 Winchester Moose Lodge 1 Nov 2025
MUSIC USD 34 TO 500

Bright Box Halloween Party ft. Dj Ophie + Special Guest Dj Curfew

 Bright Box Theater 31 Oct 2025
HALLOWEEN

More things to do in Winchester

Live Music
Festivals
Christmas Markets & Fairs
New Year
Pop-Ups
Halloween
Thanksgiving
Carnivals
Christmas Carols
Day Of The Dead
Christmas Light Displays
Trick Or Treat
Christmas Wreath Workshops
Trunk Or Treat
Comedy
Bar Crawls