Entertainment events in Winchester

Check out happening entertainment events all around Winchester, VA

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

Sunflower Festival

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

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

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

Heavy Metal Storm - Pennterra, Monolith and Priest Unleashed!

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

Sirbaugh Acres presents: The Return of Terry Oates & the Mudcats 2025!

 Sat, 27 Sep at 08:00 pm Backseat Bar & Grill

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

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

Backseat's Haunted Metal Bash

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

Rodeo Disco Night- Vibrissa Winchester

 Fri, 19 Sep at 07:00 pm Vibrissa Beer (Winchester, VA)

Comedy: Tom Foss and Lucas Bohn

 Fri, 19 Sep at 07:00 pm 186 North Loudoun Street, Winchester, VA

Reggaeton De Ayer Y Hoy Ft. DJ Suelto & DJ LJ - 21+

 Sat, 20 Sep at 09:00 pm Bright Box (Winchester, VA)

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

 Sat, 04 Oct at 08:00 pm Backseat Events

Trunk or Treat on Loudoun Street!

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

90s Throwback Party ft. DJ OPHIE

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

2025 Addicted To Hope Rally

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

An Evening of Magic with David Anthony - 7PM

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

Caleb Michael Gordon Group

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

Karaoke Night with Route 11 DJ

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

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

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

 Fri, 03 Oct at 10:00 pm The Monument VA

Neighborhood Nights

 Fri, 12 Sep at 05:00 pm 2024 Harvest Dr, Winchester, VA 22601-2795, United States

2025 Together Women's Conference

Fri, 10 Oct at 06:00 pm 2080 N Frederick Pike, 22603

Build Your Own CEMETARIUM!

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

Build Your Own CEMETARIUM!

 Sat, 25 Oct at 06:00 pm 105 Millwood Ave, Winchester, VA, United States, Virginia 22601

Karaoke Night with Route 11 DJ

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

Live Music with Jim Snedeker

 Fri, 19 Sep at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Una Tarde Familiar en Estilo Frida/Family Evening, Frida Style

 Sat, 13 Sep at 04:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Yappy Hour- Harvest

 Fri, 19 Sep at 04:00 pm 4063 Middle Rd, 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

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

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

Live Loud: Kickin’ Valentina + Bad Marriage

 Sat, 13 Sep at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Latin Festival Fundraiser

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

Classical at the MSV: An Afternoon of Schumann

 Sat, 27 Sep at 02:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Halloween Party!!

 Sat, 18 Oct at 06:00 pm 164 Poorhouse Rd, Winchester, VA, United States, Virginia 22602

AFM at Skyline Harley Davidson!

 Thu, 18 Sep at 06:00 pm Grove's Winchester Harley-Davidson

Jill Fulton Band @ Piccadilly's Public House

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

5-Elemental Lotus Healing Class

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

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

Graham Taylor OPC-WATTS Concert & Meal Fundraiser

 Sat, 20 Sep at 05:00 pm 217 Opequon Church Ln, Winchester, VA, United States, Virginia 22602

Tintype Portrait Sessions

 Sun, 14 Sep at 09:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Texas Hippie Coalition

 Thu, 16 Oct at 07:00 pm Backseat Events

Saving Abel with Anger Box

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

Bam Bam's BBQ at James Charles Winery

 Sat, 06 Sep at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Winchester Swing Dance Lesson & Social Dancing

 Thu, 11 Sep at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Grateful Allman Band Experience at The Monument Winchester VA Sept 13

 Sat, 13 Sep at 07:00 pm The Monument Winchester, VA

3rd Annual Alumni Picnic!

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

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

 Sat, 27 Sep at 09:30 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

Live Music with Jayelynn Lee

 Sat, 06 Sep at 04:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Winchester Elks

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

Jake Kohn & Low Water Bridge Band

 Fri, 03 Oct at 07:00 pm The Monument - VA

The Faire at Canterbury

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

Texas Hippie Coalition & Friends

 Fri, 17 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

Ver Azul

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

Winchester Elks Lodge - Tuff Luck Band

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

MPAA Cash Party Planning Meeting

Mon, 15 Sep at 06:00 pm Poblanos Mexican Grill

Winchester Elks Lodge

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

Emo Night Karaoke 10/3 @ Bright Box Theater

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

Bag Bingo Fundraiser

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

2025 Winchester Medical Center NICU Reunion

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

Anything But A Cup Party!

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

The Lowdown Drifters at The Monument

 Sun, 05 Oct at 07:00 pm The Monument

Brian Head Welch and Friends

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

Pandora's Box - Aerosmith Tribute Band

 Fri, 10 Oct at 07:00 pm Backseat Events

Karaoke 🎤

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

Winchester Moose Lodge

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

Cash Party Planning Meeting

Wed, 15 Oct at 06:00 pm Poblanos Mexican Grill

Aaron Tippin at Backseat Events

 Sat, 08 Nov at 08:00 pm Backseat Events

Katie's Halloween Cash Party

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

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

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

Cash Party

 Sat, 24 Jan at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

A Christmas Carol at Winchester Little Theatre Inc.

 Fri, 07 Nov Winchester Little Theatre Inc.

Trivia @ DCBC: Broadway Musicals!

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

Murphy's Bluegrass Bandits

 Sun, 28 Sep at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Karaoke Night with Route 11 DJ

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

West Oaks Farm Market - Mack Berry

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

Trainwreck LIVE at WOFM Fall Festival

 Sat, 18 Oct at 04:00 am 4305 Middle Rd, Winchester, VA 22602, United States

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Night Of Comedy at What's New Worship

 Sat, 04 Oct at 06:30 pm 2249 Valor Dr, Winchester, VA 22601-3698, United States

MSV at Night: The Lua Project

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

Children's Choir Kick Off!

 Wed, 10 Sep at 04:30 am 116 S Loudoun St, Winchester, VA, United States, Virginia 22601

Melanie Pearl Live at Valerie Hill

 Sun, 21 Sep at 02:00 pm Valerie Hill Vineyard & Winery

Sauce It Up

 Sun, 12 Oct at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Winchester Moose NYE Celebration - Tuff Luck Band

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

Holiday Concert: Yesterday Swing Orchestra

 Sun, 14 Dec at 03:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Saving Abel

 Wed, 15 Oct at 07:00 pm Backseat Events

Cash Party Planning

Mon, 17 Nov at 06:00 pm Poblanos Mexican Grill

Backseat Event Center - Pre NYE Party

 Sat, 27 Dec at 02:00 pm 114 Full House Dr, Winchester, VA 22603-4645, United States

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

Lonestar at Backseat Events

 Fri, 19 Sep at 08:00 pm Backseat Events

Lonestar

 Thu, 18 Sep at 07:00 pm Backseat Events

Holiday Bluegrass Concert: Jack Dunlap

 Sun, 07 Dec at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601