Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

Farm Concert - CAZHMIERE at West Oaks!

 Fri, 15 Aug at 07:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Farm Concert - Souled Out at West Oaks!

 Fri, 19 Sep at 07:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

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

 Sun, 07 Sep at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

West Oaks Apple Harvest Festival!

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

Harvest Hoedown

 Sat, 27 Sep at 05:00 pm Landfall Lodge

Gardens at Night: Oh Blackwater & Space Cowboy

 Fri, 12 Sep at 07:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Fiddles & Fifths 2025

 Sat, 13 Sep at 01:00 pm Shenandoah Valley Civil War Museum

Caleb Michael Gordon

 Sat, 16 Aug at 07:30 pm 28 W Hart Street, Winchester, VA, United States, Virginia 22601

90s Throwback Party ft. DJ OPHIE

 Sat, 06 Sep at 09:00 pm Bright Box Theater

Bones Owen at The Monument

 Sat, 30 Aug The Monument

Kelly Bell Band LIVE at Bright Box

 Fri, 22 Aug at 08:00 pm Bright Box Theater

Bottle Shock Live!

 Fri, 22 Aug at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

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

Help Pete kick cancers a**!

 Sat, 16 Aug at 07:00 pm Backseat Events

Jill Fulton Band @ Piccadilly's Public House

 Sat, 13 Sep at 07:00 pm Piccadilly's Public House and Restaurant

An Evening of Magic with David Anthony - 7PM

 Fri, 12 Sep at 07:00 pm Bright Box Theater

Bluegrass on the Farm

Thu, 14 Aug at 06:00 pm 2502 N. Frederick Pike, Winchester, VA

End Of Summer Bash Drag Show!

 Sat, 30 Aug at 08:00 pm 320 N Cameron St, Winchester, VA, United States, Virginia 22601 USD 13 to 23

Karaoke Night with Route 11 DJ

 Fri, 26 Sep at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Trunk or Treat on Loudoun Street!

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

Ver Azul

Sat, 27 Sep at 07:30 pm 28 W Hart Street, Winchester, VA, United States, Virginia 22601

Sunflower Festival

Sat, 06 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Caleb Michael Gordon Group

 Sat, 18 Oct at 07:30 pm 28 W Hart St, Winchester, VA 22601-4513, United States

Pandora's Box - The Ultimate Tribute to Aerosmith

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

Next Stop Comedy at The Cider House

 Fri, 26 Sep at 07:30 pm The Cider House

Emo Night Karaoke 10/3 @ Bright Box Theater

 Fri, 03 Oct at 08:00 pm Bright Box Theater USD 21

Mx. Winchester Pride 2025 Pageant

 Sat, 30 Aug at 06:00 pm Bright Box Theater

Melanie Pearl Live at Valerie Hill

 Fri, 22 Aug at 06:00 pm Valerie Hill Vineyard & Winery

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

 Sat, 04 Oct at 08:00 pm 186 North Loudoun Street, Winchester, VA

Saving Abel with Anger Box

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

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

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

3rd Annual Alumni Picnic!

 Sat, 13 Sep at 12:00 pm Kiwanis Club II Pavilion | 812 Oak Drive , Winchester, VA 22601

Roots & Rhythm: Hip Hop/Street Styles Dance Classes with Amil

 Thu, 21 Aug at 05:15 pm 302 S Loudoun Street, Winchester, VA

Silverada w/ Hannah Dasher and special guest Jesse Milness

 Sat, 16 Aug at 07:00 pm Bright Box Theater USD 23 to 29

Wine Club Release Party at Briedé Family Vineyards

 Sun, 17 Aug at 01:00 pm 450 Green Spring Rd, Winchester, VA, United States, Virginia 22603

Winchester Elks Lodge

 Fri, 19 Sep at 07:00 pm 466 Front Royal Pike, Winchester, VA 22602-7315, United States

Auditions for 2025-2026 Concert Season

 Tue, 19 Aug at 06:30 pm First Baptist Church Winchester, VA

2025 Addicted To Hope Rally

 Sat, 06 Sep at 04:00 pm Valley Heath Cancer Center

J&J Entertainment presents: Northeast Groovers live @ Backseat Events

 Fri, 22 Aug at 08:00 pm Backseat Events

Dancing Thru the Decades

 Sat, 23 Aug at 06:00 pm Backseat Events

Backseat's Haunted Metal Bash

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

Trivia @ DCBC: All Things NFL

 Wed, 03 Sep at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Improv Comedy with Porkchop Volcano - Bright Box

 Fri, 05 Sep at 07:00 pm Bright Box Theater

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

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

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

 Sat, 04 Oct at 08:00 pm Backseat Events

Open House in Winchester, Saturday August 16th 2025

 Sat, 16 Aug at 10:00 am Italia Performing Arts

Latin Festival Fundraiser

 Sat, 20 Sep at 04:30 pm Braddock Street United Methodist Church

Marvel (MCU) Trivia with Trivia Nate!

 Mon, 25 Aug at 06:30 pm 320 N Cameron St, Winchester, VA

An Evening with the Kelly Bell Band

 Fri, 22 Aug at 08:00 pm Bright Box Theater

Winchester Moose Lodge

 Sat, 08 Nov at 07:00 pm 215 E Cork St, Winchester, VA 22601-5018, United States

One Haute Summer Night

 Thu, 14 Aug at 07:00 pm The Cider House USD 18

Rally on Valley

 Sat, 23 Aug at 10:00 am 2818 Valley Avenue, Winchester, VA

Jimmy Lee Live!

 Sun, 17 Aug at 01:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Winchester Sports Card Pokémon & Collectibles Show August 30

 Sat, 30 Aug at 09:00 am Millwood Station Bingo Hall Free

Live Music with Lex Sacco

 Fri, 15 Aug at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

15th Annual Patsy Cline Block Party

 Sat, 30 Aug at 10:00 am 608 South Kent Street, Winchester, VA, United States, Virginia 22601

Live Music with Twisted Roots

 Sat, 23 Aug at 03:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

🍗 First Friday Fun: Wings & Things Party at Nibblins!

 Fri, 05 Sep at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Community Yard Sale

 Sat, 30 Aug at 10:00 am 401 Campus Blvd, Winchester, VA, United States, Virginia 22601

Marvelous Macaron

 Sat, 23 Aug at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

R.A.M.P Fest! @Jim Barnett Skate Park

 Sat, 30 Aug at 11:00 am Jim Barnett Park USD 10

The Flying Ivories: Dueling Pianos (7PM SHOW) - ALL AGES

 Sat, 27 Sep at 07:00 pm Bright Box Theater

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

The Faire at Canterbury

 Sat, 20 Sep at 10:00 am 300 Westminster Canterbury Drive, Winchester, VA, United States, Virginia 22603

The Flying Ivories: Dueling Pianos (9:30PM SHOW) - 18+

 Sat, 27 Sep at 09:30 pm Bright Box Theater

First Responder Thank You Event

 Sun, 17 Aug at 02:00 pm 135 N Braddock St, Winchester, VA

Winchester Elks

Sat, 27 Sep at 07:00 pm Fraternal Order of Elks Lodge 867

FREE STANDUP COMEDY! At Backseat Bar & Grill!

Tue, 19 Aug at 06:30 pm Backseat Bar and Grill

Jake Kohn & Low Water Bridge Band

 Fri, 03 Oct The Monument - VA

Lyndsie Nicholson Live!

 Sat, 30 Aug at 01:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Pandora's Box - Aerosmith Tribute Band

 Fri, 10 Oct at 07:00 pm Backseat Events

Katie's Halloween Cash Party

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

Karaoke Night with Route 11 DJ

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

The Lowdown Drifters at The Monument

 Sun, 05 Oct The Monument

Aaron Tippin at Backseat Events

 Sat, 08 Nov at 08:00 pm Backseat Events

Trivia @ DCBC: Broadway Musicals!

 Wed, 17 Sep at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

West Oaks Farm Market - Mack Berry

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

Karaoke 🎤

Sun, 17 Aug at 04:00 pm Granny's Place

A Christmas Carol at Winchester Little Theatre Inc.

 Fri, 07 Nov at 08:00 pm Winchester Little Theatre Inc.

Winchester Moose NYE Celebration - Tuff Luck Band

Wed, 31 Dec at 06:00 pm Winchester Moose Family Center 1283

Spots & Sips Paint Event at Chick-fil-A Pleasant Valley Road

 Wed, 20 Aug at 04:00 pm 2230 S Pleasant Valley Rd, 22601

MSV at Night: The Lua Project

 Fri, 26 Sep at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Game Night!

 Mon, 25 Aug at 06:00 pm 1104 Amherst St, Winchester, VA 22601-3340, United States

PICKLECHESTER! Dill Pickers at West Oaks Farm Market Sunday, September 7, 2025

 Sun, 07 Sep at 02:00 pm West Oaks Farm Market

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

Karaoke 🎤

Sun, 21 Sep at 04:00 pm Granny's Place

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

 Fri, 22 Aug at 06:30 pm Bright Box Theater Free

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

Dill Pickers at West Oaks Farm Market October 11, 2025

 Sat, 11 Oct at 12:30 pm West Oaks Farm Market

Trainwreck LIVE at WOFM Fall Festival

 Sun, 19 Oct at 01:00 pm West Oaks Farm Market

MSV at Night: Zac Townsend and the Mudcats

 Fri, 22 Aug at 05:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Lonestar at Backseat Events

 Fri, 19 Sep at 08:00 pm Backseat Events

Lonestar

 Thu, 18 Sep Backseat Events