Music Festivals near Sperryville, VA.

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 ....

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 ....

LoCo Fest 2025

• Aug. 31 - Aug 31, 2025
• 868 Estate Vineyards - Purcellville, VA USA

• Music

• $10 - $25

Get ready for a spectacular day of music, fun, and community spirit at the 8th Annual LoCo Fest, taking place at the beautiful 868 Estate Vineyards in ....

Old Town After Hours

• Aug. 29 - Aug 29, 2025
• Main Street - Warrenton, VA USA

• Music

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

Old Town After Hours

• Aug. 22 - Aug 22, 2025
• Main Street - Warrenton, VA USA

• Music

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

Old Town After Hours

• Aug. 15 - Aug 15, 2025
• Main Street - Warrenton, VA USA

• Music

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

Old Town After Hours

• Aug. 8 - Aug 8, 2025
• Main Street - Warrenton, VA USA

• Music

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

A Tribute to Jimmy Buffett - The Chris Sacks Band at Burnside Farms

• Jul. 26 - Jul 26, 2025
• Burnside Farms - Nokesville, VA USA

• Music

• $10 - $25

July 26 is for the beachy dreamers and barefoot groovers at Burnside Farms—The Chris Sacks Band will have us swaying to Jimmy Buffett classics and sun ....

Old Town After Hours

• Jul. 25 - Jul 25, 2025
• Main Street - Warrenton, VA USA

• Music

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

Tribute to the 80s - Shades of Grey at Burnside Farms

• Jul. 19 - Jul 19, 2025
• Burnside Farms - Nokesville, VA USA

• Music

• $10 - $25

We’re moonwalking back to the 80s with Shades of Grey. Dust off those neon leg warmers and get ready to bust a move as they channel your favorite thro ....

Swift Nation - A Taylor Swift Tribute Band at Burnside Farms

• Jul. 12 - Jul 12, 2025
• Burnside Farms - Nokesville, VA USA

• Music

• $10 - $25

Are you ready for it? Swift Nation kicks things off on July 12—they’re the ultimate live-band sing-along through all of Taylor Swift’s eras. From spar ....

Mountain Run Winery's 9th Anniversary

• Jul. 12 - Jul 12, 2025
• Mountain Run Winery - Culpeper, VA USA

• Music

Come out Saturday, July 12th to celebrate with us. It's going to be a great day to enjoy live music and fun for the whole family. Starting at one we h ....

Old Town After Hours

• Jul. 11 - Jul 11, 2025
• Main Street - Warrenton, VA USA

• Music

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

MUSIC IN THE GAP—Born Cross Eyed brings The Dead alive, Friday July 11. FREE! Lawn/Gap Bar open at 6

• Jul. 11 - Jul 11, 2025
• Hillsboro Old Stone School - Hillsboro, VA USA

• Music

• FREE!!

Among the region's favorite music events,Hillsboro's FREE Music in The Gap Summer Concert Series Under the Stars kicks off the 2025 season with Born C ....

Chris Hammock at Mountain Run Winery

• Jun. 28 - Jun 28, 2025
• Mountain Run Winery - Culpeper, VA USA

• Music

El Jefe Street Eats will be onsite all afternoon if you need delicious eats as well. ....

Anniversary Party 80's Style at Solace Brewing Co. in Sterling

• Jun. 14 - Jun 14, 2025
• Solace Brewing Company - Sterling, VA USA

• Music

Doors open at 11AM for a fun filled day of 80's throwbacks. Live Music w/Lula Grace McCain from Noon - 2PM 80's Dance Party w/Dance Kings of Leesbur ....

Land Beer Fest

• Jun. 7 - Jun 7, 2025
• Wheatland Spring Farm + Brewery - Waterford, VA USA

• Music

MUSIC Live musical performance by national-touring band Palmyra. Opening music by a duo of the local Legends, Karma CreAk. BEVERAGE Special bottles f ....

Fredericksburg Greek Festival

• Jun. 7 - Jun 8, 2025
• 12326 Spotswood Furnace Rd - Fredericksburg, VA USA

• Arts (Performing Arts)
• Community (Family & Kids)
• Community (Fundraiser)
• Food / Wine / Beer
• Music

• FREE!!

Be Greek for a day! Food, music, church tours, spirits! Free entry and parking! ....

Virginia Black Bear Festival 2025

• Jun. 7 - Jun 7, 2025
• 40 Celt Rd - Stanardsville, VA USA

• Community (Family & Kids)
• Food / Wine / Beer
• Music
• Outdoor / Recreation
• Seasonal (Spring)

• FREE!!

Celebrate the 2nd annual Virginia Black Bear Festival in downtown Stanardsville.  Interact with experts and discover regional outdoor opport ....

A Fest Less Ordinary--Celebrating American Music in Western Loudoun on May 31, 2025

• May. 31 - May 31, 2025
• A Farm Less Ordinary - Purcellville, VA USA

• Music

• $25 - $50

A FEST LESS ORDINARY: A Celebration of American MusicSaturday, May 31, 2025 | 3-9 pm | Purcellville, VA Get ready for an incredible lineup of musical ....