Winchester Live Music Events

Samhain Market & Zombie Walk

105 Millwood Ave, Winchester, VA, United States, Virginia 22601 12 Oct 2025

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

4305 Middle Road, Winchester, VA, United States, Virginia 22602 7 Sep 2025

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 6 Sep 2025

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 30 Aug 2025

Harvest Hoedown

Landfall Lodge 27 Sep 2025

Gardens at Night: Oh Blackwater & Space Cowboy

901 Amherst St, Winchester, VA, United States, Virginia 22601 12 Sep 2025

Fiddles & Fifths 2025

Shenandoah Valley Civil War Museum 13 Sep 2025

West Oaks Apple Harvest Festival!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 5 Oct 2025

Bottle Shock Live!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 22 Aug 2025

Aaron Tippin - Stand for America at Backseat Events!

114 Full House Drive , Winchester, VA, United States, Virginia 22603 8 Nov 2025

90s Throwback Party ft. DJ OPHIE

Bright Box Theater 6 Sep 2025

2025 Addicted To Hope Rally

Valley Heath Cancer Center 6 Sep 2025

Caleb Michael Gordon Group

28 W Hart St, Winchester, VA 22601-4513, United States 18 Oct 2025

Melanie Pearl Live at Valerie Hill

Valerie Hill Vineyard & Winery 22 Aug 2025

Bam Bam's BBQ at James Charles Winery

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 6 Sep 2025

" Let It Begin Tour"

Backseat Events 9 Oct 2025

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

186 North Loudoun Street, Winchester, VA 4 Oct 2025

Lyndsie Nicholson Live!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 30 Aug 2025

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

Backseat Events 22 Aug 2025

First Friday

Old Town Winchester Walking Mall 5 Sep 2025

Kelly Bell Band LIVE at Bright Box

Bright Box Theater 22 Aug 2025

Gray Matter @Winchester Moose

Winchester Moose Family Center 1283 25 Oct 2025

Micky & The Motorcars

Bright Box Theater 4 Oct 2025

An Evening with the Kelly Bell Band

Bright Box Theater 22 Aug 2025

Celebracion of Winchester

Taylor Pavilion Winchester 20 Sep 2025

Penntera, Monolith & Priest Unleashed - High Voltage ROCK Night

Backseat Events 4 Oct 2025

Latin Festival Fundraiser

Braddock Street United Methodist Church 20 Sep 2025

Jill Fulton Band @ Piccadilly's Public House

Piccadilly's Public House and Restaurant 13 Sep 2025

15th Annual Patsy Cline Block Party

608 South Kent Street, Winchester, VA, United States, Virginia 22601 30 Aug 2025

Dancing Thru the Decades

Backseat Events 7 Feb 2026

Sin City at Backseat Bar & Grill

Backseat Bar and Grill 15 Nov 2025

Pandora's Box - The Ultimate Tribute to Aerosmith

114 Full House Drive , Winchester, VA, United States, Virginia 22603 11 Oct 2025

Live Music with Twisted Roots

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 23 Aug 2025

First Friday

Old Town Winchester Walking Mall 3 Oct 2025

Saving Abel with Anger Box

114 Full House Drive , Winchester, VA, United States, Virginia 22603 16 Oct 2025

Real Riddim Hours Feat. ZUBAH + KHOLD

The Monument VA 12 Sep 2025

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

Brandt Student Center 1 Nov 2025

Rally on Valley

2818 Valley Avenue, Winchester, VA 23 Aug 2025

Ver Azul

28 W Hart Street, Winchester, VA, United States, Virginia 22601 27 Sep 2025

Backseat's Haunted Metal Bash

114 Full House Drive , Winchester, VA, United States, Virginia 22603 31 Oct 2025

West Oaks Fall Harvest Festival!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 19 Oct 2025

Emo Night Karaoke 10/3 @ Bright Box Theater

Bright Box Theater 3 Oct 2025

3rd Annual Alumni Picnic!

Kiwanis Club II Pavilion | 812 Oak Drive , Winchester, VA 22601 13 Sep 2025

Texas Hippie Coalition & Friends

114 Full House Drive , Winchester, VA, United States, Virginia 22603 17 Oct 2025

Acoustic Soul at Piccadilly’s Public House

Piccadilly's Public House and Restaurant 12 Sep 2025

Logan Moore Friday Night!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 Aug 2025

Sever Red, Rise Among Rivals, VEER @Backseat Events

Backseat Events 26 Sep 2025

Mabon Harvest Market

105 Millwood Ave, Winchester, VA 21 Sep 2025

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

Backseat Events 26 Sep 2025

Community Yard Sale

401 Campus Blvd, Winchester, VA, United States, Virginia 22601 30 Aug 2025

Jake Kohn & Low Water Bridge Band

The Monument - VA 3 Oct 2025

Local Boy Timmy @ Gus's Bar & BBQ

Gus's Bar & BBQ 11 Oct 2025

Chris Brunn Live!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 24 Aug 2025

Winchester Moose Lodge

215 E Cork St, Winchester, VA 22601-5018, United States 8 Nov 2025

Aaron Tippin at Backseat Events

Backseat Events 8 Nov 2025

Drum Fever - Play To The Next Level

28 W Hart Street, Winchester, VA, United States, Virginia 22601 8 Sep 2025

Trivia @ DCBC: Broadway Musicals!

160 N Loudoun St, Winchester, VA, United States, Virginia 22601 17 Sep 2025

MSV at Night: The Lua Project

901 Amherst St, Winchester, VA, United States, Virginia 22601 26 Sep 2025

Texas Hippie Coalition

Backseat Events 16 Oct 2025

Winchester Moose NYE Celebration - Tuff Luck Band

Winchester Moose Family Center 1283 31 Dec 2025

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

West Oaks Farm Market 7 Sep 2025

Dill Pickers at West Oaks Farm Market October 11, 2025

West Oaks Farm Market 11 Oct 2025

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 19 Oct 2025

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025

MSV at Night: Zac Townsend and the Mudcats

901 Amherst St, Winchester, VA, United States, Virginia 22601 22 Aug 2025

Lonestar at Backseat Events

Backseat Events 19 Sep 2025