Music Festivals near Winchester, VA.

Reynolds Memorial Baptist Church's 100 Year Anniversary Celebration

• Oct. 4 - Oct 4, 2025
• 3748 Sperryville Pike - Sperryville, VA USA

• Music

This free event will begin at 4:00 PM. There will be a country gospel band, BBQ, a variety of side dishes and desserts, plus games and a cake walk. ....

Super Trans AM – The Ultimate ‘70s Rock Experience - September 27 - Tarara

• Sep. 27 - Sep 27, 2025
• Tarara Summer Concert Series - Leesburg, VA USA

• Music

• $10 - $25

???? Super Trans AM – The Ultimate ‘70s Rock Experience LIVE at Tarara! ???? Buckle up, because Super Trans AM is taking you on a high-octane ride th ....

Live Music by Steve Boyd & Friends

• Sep. 27 - Sep 27, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Old Town After Hours

• Sep. 26 - Sep 26, 2025
• Main Street - Warrenton, VA USA

• Music

Live music on Main Street, Fridays 6-9 pm ....

Live Music by Brett Baboorian

• Sep. 26 - Sep 26, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Rock and Popcycles

• Sep. 21 - Sep 21, 2025
• Emmanuel Parish House - Middleburg, VA USA

• Music

Cool rock & roll favorites from the ‘60s and ‘70’s dished out by the Bank Street Band on the porch of Emmanuel Church’s Parish House. Even cooler pops ....

Live Music by Elle & Ron

• Sep. 21 - Sep 21, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

White Ford Bronco – The Ultimate ‘90s Party - September 20 - Tarara

• Sep. 20 - Sep 20, 2025
• Tarara Summer Concert Series - Leesburg, VA USA

• Music

• $10 - $25

???? White Ford Bronco – The Ultimate ‘90s Party LIVE at Tarara! ???? Break out your flannel, dust off your Discman, and get ready for the ultimate ‘ ....

Live Music by Scott Kurt

• Sep. 20 - Sep 20, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Echos in the Pines: Summer Campout Series

• Sep. 20 - Sep 20, 2025
• Verdun Adventure Bound - Rixeyville, USA

• Music

• FREE!!
• $1 - $10
• $10 - $25

Enjoy an evening under the stars at Echos in the Pines; Verdun's Summer Camp-Out Series! Enjoy great, local music and then camp out on the Verdun grou ....

Old Town After Hours

• Sep. 19 - Sep 19, 2025
• Main Street - Warrenton, VA USA

• Music

Live music on Main Street, Fridays 6-9 pm ....

Live Music by Bill Bowman

• Sep. 14 - Sep 14, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

The Warped Tour Band, All The Blink Things, & Dookie - September 13 - Tarara

• Sep. 13 - Sep 13, 2025
• Tarara Summer Concert Series - Leesburg, VA USA

• Music

• $10 - $25

???? The Warped Tour Band, All The Blink Things & Dookie – The Ultimate Pop-Punk & Emo Night LIVE at Tarara! ???? Calling all emo kids, pop-punk love ....

George Katsos Returns to Harpers Ferry Brewing For His Final Show in 2025

• Sep. 13 - Sep 13, 2025
• 37412 Adventure Center Ln - Purcellville, VA USA

• Music

George Katsos returns to Harpers Ferry Brewing for his final show in 2025. Come join the fun with classics from the last century outside of the beltwa ....

Live Music by Shelly & The Mudcats

• Sep. 13 - Sep 13, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

???? Eclectic Company LIVE! ???? Friday, September 12th (7-10pm)

• Sep. 12 - Sep 12, 2025
• Heroic Axe - Warrenton, VA USA

• Music

???? Eclectic Company LIVE! ???? Friday, September 12th (7-10pm) Covering a large range of genres, lead singer, Darren Tapscott, never fails to get th ....

Old Town After Hours

• Sep. 12 - Sep 12, 2025
• Main Street - Warrenton, VA USA

• Music

Live music on Main Street, Fridays 6-9 pm ....

Live Music by Scott Kurt

• Sep. 12 - Sep 12, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Live Music by Sharif

• Sep. 7 - Sep 7, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

The Sensational Soul Cruisers – A Night of Motown Magic - September 6 - Tarara

• Sep. 6 - Sep 6, 2025
• Tarara Summer Concert Series - Leesburg, VA USA

• Music

• $10 - $25

???? The Sensational Soul Cruisers – A Night of Motown Magic LIVE at Tarara! ???? Get ready to dance, groove, and sing along to the greatest hits of ....

Live Music by Derek Kretzer & Friends

• Sep. 6 - Sep 6, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

US Open Watch Party

• Sep. 6 - Sep 7, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Join us for a day of tennis-inspired fun, delicious food, specialty drinks, and good vibes. We’ll be streaming the tournament live, serving up food, a ....

The 21st Annual Watermelon Pickers' Fest

• Sep. 4 - Sep 6, 2025
• Clarke County Ruritan Fairgrounds - Berryville, VA USA

• Music

• $100 - $250

Watermelon Pickers’ Fest is back for three incredible days of music, workshops, jamming, and community. This year’s lineup features must-see headliner ....

Jimmy Buffett Margaritaville Bash

• Sep. 1 - Sep 1, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Kick back and sail into paradise this Labor Day at our Jimmy Buffett Margaritaville Party! ???? We're transforming the space into a tropical getaway w ....