Upcoming Food & Drinks Events

Farm Concert - Souled Out at West Oaks!

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 19 Sep 2025
ENTERTAINMENT

Fiddles & Fifths 2025

 Shenandoah Valley Civil War Museum 13 Sep 2025
MUSIC

West Oaks Apple Harvest Festival!

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 5 Oct 2025
FESTIVALS

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Upcoming Live Music Events

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 30 Aug 2025

Gardens at Night: Oh Blackwater & Space Cowboy

 901 Amherst St, Winchester, VA, United States, Virginia 22601 12 Sep 2025
KIDS

Harvest Hoedown

 Landfall Lodge 27 Sep 2025
MUSIC

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Upcoming Festivals Events

PICKLE-CHESTER! The West Oaks 2nd Annual Pickle Festival!

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 7 Sep 2025
FESTIVALS

Samhain Market & Zombie Walk

 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 12 Oct 2025

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 6 Sep 2025
FESTIVALS

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Upcoming Halloween Events

Harvest Market @ WBW

 320 N Cameron St, Winchester, VA 27 Sep 2025
FESTIVALS

Trunk or Treat on Loudoun Street!

 302 S Loudoun Street, Winchester, VA 18 Oct 2025
HALLOWEEN

Samhain Luna Market 2025

 125 S. Loudoun Street, Winchester, VA 11 Oct 2025
HALLOWEEN

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Upcoming Comedy Events

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

 Blue Fox Billiards, Bar and Grill 20 Sep 2025

An Evening of Magic with David Anthony - 7PM

 Bright Box Theater 12 Sep 2025
COMEDY

Quotable Movie Night

14 W Boscawen St, Winchester, VA 28 Aug 2025
ENTERTAINMENT

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Upcoming Car Shows Events

Wings and Wheels - Winchester, VA

 Winchester Regional Airport - OKV 18 Oct 2025
CAR-SHOWS

JWHS FFA Car Show- Fast and Furious Autos

 161 Apple Pie Ridge Road, Winchester, VA, United States, Virginia 22603 6 Sep 2025
CAR-SHOWS

Spring Arbor Cruise In

 2093 Northwestern Pike, Winchester, VA, United States, Virginia 22603 7 Sep 2025
NONPROFIT

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Upcoming Labor Day Events

15th Annual Patsy Cline Block Party

 608 South Kent Street, Winchester, VA, United States, Virginia 22601 30 Aug 2025
ENTERTAINMENT

Pre Spooky Season Bash

125 S. Loudoun Street, Winchester, VA 29 Aug 2025
LABOR-DAY

Campout at “Winning at Winchester”

 Church of Christ at Mountain View 29 Aug 2025
LABOR-DAY

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Upcoming Music Festivals Events

Micky & The Motorcars

 Bright Box Theater 4 Oct 2025
COUNTRY-MUSIC-FESTIVALS

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

 114 Full House Drive, Winchester, VA 4 Oct 2025
MUSIC

Latin Festival Fundraiser

 Braddock Street United Methodist Church 20 Sep 2025
NONPROFIT

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Trending Events in Winchester

Rodeo Disco Night- Vibrissa Winchester

 Vibrissa Beer (Winchester, VA) 19 Sep 2025
PARTIES

Oktoberfest @ WBW

 320 N Cameron St, Winchester, VA 20 Sep 2025
OKTOBERFEST

End Of Summer Bash Drag Show!

 320 N Cameron St, Winchester, VA, United States, Virginia 22601 30 Aug 2025
DRAG-SHOWS USD 13 TO 23

Winchester Moose Lodge 1283

 215 E Cork St, Winchester, VA 22601 6 Sep 2025

FLW BACK LIVE at PICCADILLY'S!

 Piccadilly's Public House and Restaurant 29 Aug 2025
MUSIC

Winchester Sports Card Pokémon & Collectibles Show August 30

 Millwood Station Bingo Hall 30 Aug 2025
SPORTS FREE

NAACP Winchester Area Freedom Fund Gala Fundraiser

SU, Ferrari Room, 703 University Drive, Winchester VA 20 Sep 2025
NONPROFIT

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 27 Sep 2025

Conservation Easements: Stories, Process, Possibilities

 Landfall Lodge 11 Sep 2025
FREE

Men’s Healthcare Forum ❣️ Hosted by NAACP Health Committee

1810 Roberts Street, Winchester, VA 22601 6 Sep 2025
HEALTH-WELLNESS

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 25 Oct 2025

Phelpsmore Farm Stone Soup Gathering

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 4 Sep 2025
ART

Aaron Tippin - Stand for America at Backseat Events!

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

Yuletide Mystical Market

 Raven Conjure 7 Dec 2025
HOLIDAY

Mx. Winchester Pride 2025 Pageant

 Bright Box Theater 30 Aug 2025
LGBT-PRIDE

More things to do in Winchester

Food & Drinks
Live Music
Festivals
Halloween
Comedy
Car Shows
Labor Day
Oktoberfest
Music Festivals
Rodeo
Pop-Ups