Upcoming Food & Drinks Events

West Oaks Apple Harvest Festival!

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

Pierogis!!

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 25 Oct 2025
WORKSHOPS

2025 Winchester Medical Center NICU Reunion

 West Oaks Farm Market 12 Oct 2025
KARAOKE

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Upcoming Live Music Events

Pandora's Box - The Ultimate Tribute to Aerosmith & Special Guests AIRMONT ROAD - SAT OCT 11

 114 Full House Drive , Winchester, VA, United States, Virginia 22603 11 Oct 2025
ENTERTAINMENT

Backseat's Haunted Metal Bash

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

The Bass Club Presents: G-SPACE | SATURN RETURN TOUR

 Bright Box Theater 11 Oct 2025
MUSIC

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Upcoming Halloween Events

Samhain Market & Zombie Walk

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

Trunk or Treat on Loudoun Street!

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

Build Your Own CEMETARIUM!

 105 Millwood Ave, Winchester, VA, United States, Virginia 22601 10 Oct 2025
ENTERTAINMENT

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Upcoming Festivals Events

Native Plant Festival

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 4 Oct 2025
FESTIVALS

Farm & Maker’s Saturday Market

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

Samhain Luna Market 2025

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

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Trending Events in Winchester

Old Town Merchant Trick or Treat

Downtown Walking Mall 25 Oct 2025
TRICK-OR-TREAT

Armies on Parade

 255 Market Street, Winchester, VA, United States, Virginia 22603 4 Oct 2025
PARADES

Wings and Wheels - Winchester, VA

 Winchester Regional Airport - OKV 18 Oct 2025
CAR-SHOWS

Oktoberfest @ Vibrissa Beer- WINCHESTER LOCATION

10 N Kent St, Winchester, VA 22601-5038, United States 4 Oct 2025
OKTOBERFEST

Valley Glasshoppers Annual Fall Glass Show and Sale

1309 Opequon Ave, Winchester, VA 22601-4401, United States 3 Oct 2025
NONPROFIT

Brian Head Welch and Friends

 2249 valor dr winchester va 8 Nov 2025
MUSIC

Night Of Comedy at What's New Worship

 2249 Valor Dr, Winchester, VA 22601-3698, United States 4 Oct 2025
COMEDY

80s Night with The Reagan Years

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

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

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

Midnight Manor Tea

 217 W Boscawen St, Winchester, VA 22601-4117, United States 24 Oct 2025
PARTIES

Boo Bounce Bash

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 24 Oct 2025
HALLOWEEN

October Full Moon Night: Harvest Moon

125 S. Loudoun Street, Winchester, VA 7 Oct 2025

The Reflex - 80's Tribute Band & The Blue Genies

 Backseat Events 23 Oct 2025
MUSIC

November Full Moon Night: Beaver Moon

125 S. Loudoun Street, Winchester, VA 5 Nov 2025

Pandora's Box - Aerosmith Tribute Band

 Backseat Events 10 Oct 2025
MUSIC

More things to do in Winchester

Food & Drinks
Live Music
Halloween
Festivals
Comedy
Carnivals
Pop-Ups
Oktoberfest
Car Shows
Parades