Live Music in Winchester

Check out happening live music events all around Winchester, VA

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

Samhain Market & Zombie Walk

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

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

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

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

Backseat's Haunted Metal Bash

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

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

 Sat, 04 Oct at 08:00 pm Backseat Events

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

Caleb Michael Gordon Group

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

" Let It Begin Tour"

 Thu, 09 Oct at 06:30 pm Backseat Events

Celebracion of Winchester

Sat, 20 Sep at 12:00 pm Taylor Pavilion Winchester

Mabon Harvest Market

 Sun, 21 Sep at 11:00 am 105 Millwood Ave, Winchester, VA

Live Music with Jim Snedeker

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

Gray Matter @Winchester Moose

 Sat, 25 Oct at 07:00 pm Winchester Moose Lodge 1283

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

Latin Festival Fundraiser

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

Jill Fulton Band @ Piccadilly's Public House

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

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

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

First Friday

 Fri, 03 Oct at 05:00 pm Old Town Winchester Walking Mall

Sin City at Backseat Bar & Grill

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

3rd Annual Alumni Picnic!

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

Acoustic Soul at Piccadilly’s Public House

 Fri, 12 Sep at 07:30 pm Piccadilly's Public House and Restaurant

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

Jake Kohn & Low Water Bridge Band

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

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

Real Riddim Hours Feat. ZUBAH + KHOLD

 Fri, 12 Sep at 09:00 pm The Monument VA

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

Wright Live presents: Sever Red, Rise Among Rivals, VEER

 Fri, 26 Sep at 07:00 pm Backseat Events USD 10

Nightrain LIVE!

 Fri, 14 Nov at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Sever Red, Rise Among Rivals, VEER @Backseat Events

 Fri, 26 Sep at 07:00 pm Backseat Events

Local Boy Timmy @ Gus's Bar & BBQ

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

Micky & The Motorcars

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

Winchester Moose Lodge

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

Aaron Tippin at Backseat Events

 Sat, 08 Nov at 08:00 pm Backseat Events

Winchester Moose Lodge

 Sat, 15 Nov at 07:00 pm 215 E Cork St, Winchester, VA 22601

Drum Fever - Play To The Next Level

 Mon, 08 Sep at 05:00 pm 28 W Hart Street, Winchester, VA, United States, Virginia 22601

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

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

Trivia @ DCBC: Broadway Musicals!

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

Drum Fever Workshop

Sun, 02 Nov at 05:00 pm 28 W Hart Street, Winchester, VA, United States, Virginia 22601

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

MSV at Night: The Lua Project

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

Melanie Pearl Live at Valerie Hill

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

Winchester Moose NYE Celebration - Tuff Luck Band

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

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