Upcoming Winchester Events

Check out what's happening all around Winchester, VA

West Oaks Apple Harvest Festival!

Sun, 05 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Wings and Wheels - Winchester, VA

Sat, 18 Oct at 10:00 am Winchester Regional Airport - OKV

Samhain Market & Zombie Walk

Sun, 12 Oct at 11:00 am 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

Trunk or Treat on Loudoun Street!

Sat, 18 Oct at 06:00 pm 302 S Loudoun Street, Winchester, VA

Native Plant Festival

Sat, 04 Oct at 10:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

Sat, 04 Oct at 08:00 pm 114 Full House Drive, Winchester, VA

Backseat's Haunted Metal Bash

Fri, 31 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

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

Sat, 11 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Build Your Own CEMETARIUM!

Fri, 10 Oct at 06:00 pm 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

80s Night with The Reagan Years

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

Boo Bounce Bash

Fri, 24 Oct at 05:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Midnight Manor Tea

Fri, 24 Oct at 06:30 pm 217 W Boscawen St, Winchester, VA 22601-4117, United States

October Full Moon Night: Harvest Moon

Tue, 07 Oct at 06:00 pm 125 S. Loudoun Street, Winchester, VA

Farm & Maker’s Saturday Market

Sat, 25 Oct at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Spooky Fun 2025

Fri, 17 Oct at 05:30 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

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

Thu, 23 Oct at 07:00 pm Backseat Events

Oktoberfest @ Vibrissa Beer- WINCHESTER LOCATION

Sat, 04 Oct at 11:00 am 10 N Kent St, Winchester, VA 22601-5038, United States

November Full Moon Night: Beaver Moon

Wed, 05 Nov at 06:00 pm 125 S. Loudoun Street, Winchester, VA

Micky & The Motorcars

Sat, 04 Oct at 07:00 pm Bright Box Theater

Yuletide Mystical Market

Sun, 07 Dec at 11:00 am Raven Conjure

Guest Reading: Half Tail Tarot

Sat, 01 Nov at 11:00 am 125 S. Loudoun Street, Winchester, VA

Holiday Market & Big Schloss Release Day!

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

Pierogis!!

Sat, 25 Oct at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

German III: Schnitzel & More

Fri, 10 Oct at 06:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

" Let It Begin Tour"

Thu, 09 Oct at 06:30 pm Backseat Events

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

Sat, 01 Nov at 06:30 pm Brandt Student Center

9th Annual Adrenaline RC Invitational

Fri, 03 Oct at 02:00 pm 246 Sulky Dr., Winchester, VA, United States, Virginia 22602

Bag Bingo Fundraiser

Sat, 11 Oct at 06:00 pm 425 Handley Blvd, 22601

An Evening with OPHSET

Fri, 17 Oct at 08:00 pm Bright Box Theater

Mid Atlantic Reptile Expo - WINCHESTER VA

Sat, 04 Oct at 09:00 am Winchester Sportsplex

Low Water Bridge Band & Jake Kohn – Co‑Headline Hometown Show

Sat, 04 Oct at 08:00 pm Taylor Pavillion Winchester Va

Nightrain - Gun N' Roses Tribute

Thu, 13 Nov at 07:00 pm Backseat Events

Aaron Tippin at Backseat Events

Sat, 08 Nov at 08:00 pm Backseat Events

Austin Meade and Elvie Shane at The Monument

Sat, 08 Nov at 07:00 pm The Monument

Saving Abel with Anger Box

Thu, 16 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Old Town Invasion

Fri, 17 Oct at 07:00 pm 14 W Boscawen St, Winchester, VA, United States, Virginia 22601

2025 Winchester Medical Center NICU Reunion

Sun, 12 Oct at 01:00 pm West Oaks Farm Market

Guided History Walking Tour of Old Town Winchester

Fri, 17 Oct at 06:00 pm 2 N Cameron St, Winchester, VA 22601-4788, United States

Local Boy Timmy @ Gus's Bar & BBQ (debut)

Sat, 11 Oct at 07:30 pm Gus's Bar & BBQ

Samhain Luna Market 2025

Sat, 11 Oct at 10:00 am 125 S. Loudoun Street, Winchester, VA

Karaoke Night with Route 11 DJ

Fri, 24 Oct at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Drum Fever Workshop

Sun, 05 Oct at 05:00 pm 28 W Hart Street, Winchester, VA, United States, Virginia 22601

Katie's Halloween Cash Party

Sat, 25 Oct at 05:30 pm Backseat Events USD 55

West Oaks Fall Harvest Festival!

Sun, 19 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Anything But A Cup Party!

Sat, 18 Oct at 02:00 pm 320 N Cameron St, Winchester, VA

Practical Tai Chi @ FPC

Sat, 04 Oct at 11:00 am First Presbyterian Church of Winchester, Virginia

Indian Butter Chicken and more

Fri, 17 Oct at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Chuggalug DUO in Winchester, VA!

Sat, 11 Oct at 07:30 pm Piccadilly's Public House and Restaurant

Aaron Tippin - Stand for America at Backseat Events!

Sat, 08 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Brian Head Welch and Friends

Sat, 08 Nov at 04:30 pm 2249 valor dr winchester va

Cedar Creek Grade Halloween Party

Sat, 01 Nov at 09:00 pm 1160 Millwood Pike, Winchester, VA, United States, Virginia 22602

Veritas Fight Series- Proving Grounds

Sat, 01 Nov at 06:00 pm Backseat Events

Handley Library Tour - Behind the Scenes

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

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

Sat, 04 Oct at 08:00 pm Backseat Events

Bright Box Feud

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

Recruit Ready Basketball Showcase

Sat, 11 Oct at 10:00 am 1001 War Memorial Dr, Winchester VA

Aaron Tippin

Fri, 07 Nov at 07:00 pm Backseat Events

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

Sat, 11 Oct at 09:00 pm Bright Box Theater

Texas Hippie Coalition

Thu, 16 Oct at 07:00 pm Backseat Events

Fire and Rescue 5K

Sat, 11 Oct at 08:00 am Village Square Restaurant and V2 Oyster Bar & Lounge

CASH PARTY

Sat, 04 Oct at 05:00 pm Winchester Moose Lodge.

Subaru Loves Pets - Annual Adoption Event

Sat, 18 Oct at 10:00 am CMA's Subaru of Winchester

The Crone and The Crow Halloween Conjuring

Fri, 31 Oct at 07:00 pm The Cider House

5-Elemental Lotus Healing Class

Sat, 25 Oct at 01:00 pm Lykens Chiropractic, Inc.

West Oaks Farm Market - Mack Berry

Sat, 04 Oct at 12:30 pm West Oaks Farm Market

TalkWalk Community Walks - October

Mon, 20 Oct at 06:00 pm 1 N Loudoun St Free

Bluegrass on the Farm

Thu, 09 Oct at 06:00 pm 2502 N. Frederick Pike, Winchester, VA

Orin Swift Wine Tasting at The Beer & Wine Depot!

Fri, 10 Oct at 04:00 pm 1863 - A Berryville Pike, Winchester, VA

Walk to End Alzheimer's Northern Shenandoah Valley

Sat, 01 Nov at 09:00 am Museum of the Shenandoah Valley

Halloween Happenings

Fri, 24 Oct at 06:00 pm 107 North Kent Street, Winchester, VA, United States, Virginia 22601

Sin City at Backseat Bar & Grill

Sat, 15 Nov at 08:30 pm Backseat Bar and Grill

Family Funday Paint Class at Easely Created

Fri, 10 Oct at 06:30 pm Easely Created Winchester

Elijah - The Lowest Tour

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

The New England Patriots vs the Buffalo Bills: Live at The Cider House

Sun, 05 Oct at 08:20 pm 30 East Piccadilly Street, Winchester, VA, United States, Virginia 22601

Four Color Fright Fest 2025!

Sat, 25 Oct at 10:00 am 80 Weems Ln, Winchester, VA, United States, Virginia 22601

One Valley Area Wide Huddle

Sat, 04 Oct at 02:00 pm FASST Sports Performance Training

Comedy Night with Ken Harvey and Taylor Mason

Sat, 04 Oct at 06:30 pm Whats New Worship USD 13

Empty Bowl Supper 2025

Fri, 07 Nov at 05:00 pm Fellowship Bible Church USD 50 to 82

Mack Berry Live at West Oaks!

Sat, 04 Oct at 12:30 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Texas Hippie Coalition & Friends

Fri, 17 Oct at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Oct Volunteer Day at Peaceful Fields Sanctuary

Sun, 05 Oct at 11:00 am Peaceful Fields Sanctuary

DMATF@The Monument

Sat, 18 Oct at 08:00 pm 186 N Loudoun St, Winchester, VA 22601-4718, United States

Vino Art Club

Fri, 24 Oct at 06:00 pm 127 S. Braddock St., Winchester, VA

Halloween Scavenger Hunt Fun Run

Thu, 23 Oct at 06:00 pm Runners' Retreat

YDC Art Classes

Sat, 04 Oct at 10:00 am 302 S Loudoun Street, Winchester, VA, United States, Virginia 22601

Halloween Happenings

Sat, 25 Oct at 06:00 pm 107 North Kent Street, Winchester, VA, United States, Virginia 22601

Pandora's Box - Aerosmith Tribute Band

Fri, 10 Oct at 07:00 pm Backseat Events

VETERAN TALES BOOK RELEASE AND SIGNING

Sat, 08 Nov at 09:00 am Solenberger's True Value Hardware

Tea & Tai Chi

Fri, 10 Oct at 11:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Chonda Pierce at Victory Church - Winchester

Fri, 31 Oct at 07:00 pm Victory Church - Winchester Free

Become a Spice Master

Sun, 05 Oct at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Oct Guided Tour of Peaceful Fields Sanctuary

Sun, 12 Oct at 02:00 pm Peaceful Fields Sanctuary USD 8

Monthly Women's Circle - Full Moon Gathering

Mon, 06 Oct at 06:00 pm Daydream Studios USD 28

Wellington 101

Fri, 07 Nov at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Gingerbread Mini Sessions

Sat, 08 Nov at 05:00 pm Downtown Walking Mall

Karaoke Night with Route 11 DJ

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

Backseat Winchester Va

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

90s Night with Doc Martin and the Flannel

Sat, 18 Oct at 07:00 pm 186 North Loudoun Street, Winchester, VA