Live Music in Winchester

Check out happening live music 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

Samhain Market & Zombie Walk

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

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

Gardens at Night: Oh Blackwater & Space Cowboy

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

Farm & Maker’s Saturday Market

Sat, 30 Aug at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Harvest Hoedown

Sat, 27 Sep at 05:00 pm Landfall Lodge

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

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

Jill Fulton Band @ Piccadilly's Public House

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

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

First Friday

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

2025 Addicted To Hope Rally

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

Emo Night Karaoke 10/3 @ Bright Box Theater

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

Melanie Pearl Live at Valerie Hill

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

"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

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

Sat, 04 Oct at 08:00 pm 186 North 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

Winchester Elks Lodge

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

Winchester Moose Lodge

Fri, 15 Aug at 07:00 pm 215 E Cork St, Winchester, VA 22601-5018, United States

Dancing Thru the Decades

Sat, 23 Aug at 06:00 pm Backseat Events

Gray Matter @Winchester Moose

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

Micky & The Motorcars

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

First Friday

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

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

Celebracion of Winchester

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

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

Rally on Valley

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

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

Sin City at Backseat Bar & Grill

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

Live Music with Twisted Roots

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

Community Yard Sale

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

Real Riddim Hours Feat. ZUBAH + KHOLD

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

West Oaks Fall Harvest Festival!

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

First Responder Thank You Event

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

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

Sever Red, Rise Among Rivals, VEER @Backseat Events

Fri, 26 Sep at 07:00 pm Backseat Events

Mabon Harvest Market

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

Chris Brunn Live!

Sun, 24 Aug at 12:30 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Logan Moore Friday Night!

Fri, 29 Aug at 01:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

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

Winchester Moose NYE Celebration - Tuff Luck Band

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

MSV at Night: The Lua Project

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

Texas Hippie Coalition

Thu, 16 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