Festivals near Sperryville, VA.

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 ....

Dumfries Fall

• Sep. 20 - Sep 20, 2025
• 17749 Main St - Dumfries, VA USA

Dumfries is presenting their Fall Festival on Saturday, September 20. If you are interested in being a vendor, please sign up using the QR code on the ....

Virginia Clay Festival - 10th Annual

• Sep. 20 - Sep 21, 2025
• William Monroe High School - Stanardsville, VA USA

• Arts (Arts & Crafts)
• Food / Wine / Beer
• Music
• Seasonal (Fall)

• FREE!!

Held in the town of Stanardsville, the Virginia Clay Festival is an art show celebrating the creative possibilities of clay. 35 of the finest clay ar ....

Old Town Manassas Oktoberfest @ Manassas Museum

• Sep. 20 - Sep 20, 2025
• The Manassas Museum - Manassas, VA USA

• Arts (Arts & Crafts)

Date: Saturday, September 20, 2025Time: 10:00 AM – 5:00 PMLocation: Manassas Museum Lawn, Old Town Manassas, VA Celebrate the season at Old Tow ....

Old Town After Hours

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

• Music

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

??Thursday Night Trivia (7-9 PM) With Rockstar DJ

• Sep. 18 - Sep 18, 2025
• Heroic Axe - Warrenton, VA USA

Rally your crew for a shot at the Champion’s Trivia Belt ??! Reservations & ?? Throwing Never Required ?? Minutes from Haymarket, Gainesville, & Warr ....

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 ....

Tribute to Patsy Cline and Don Williams

• Sep. 13 - Sep 13, 2025
• Henway Hard Cider - Bluemont, VA USA

Join the Martinsburg Chapter of Guitars For Vets at Henway Hard Cider Company in Bluemont for an evening filled with the music of Patsy Cline and Don ....

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 ....

??Thursday Night Trivia (7-9 PM) With Rockstar DJ

• Sep. 11 - Sep 11, 2025
• Heroic Axe - Warrenton, VA USA

Rally your crew for a shot at the Champion’s Trivia Belt ??! Reservations & ?? Throwing Never Required ?? Minutes from Haymarket, Gainesville, & Warr ....

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 ....

4th Annual Mad Jazz & Wine Festival

• Sep. 6 - Sep 6, 2025
• Prince Michel Vineyard \u0026 Winery - Leon, USA

• $1 - $10
• $25 - $50
• $100 - $250

We’re thrilled to invite you to the 4th Annual Mad Jazz & Wine Festival, happening Saturday, September 6, 2025, at the stunning Prince Michel Vineyard ....

??Thursday Night Trivia (7-9 PM) With Rockstar DJ

• Sep. 4 - Sep 4, 2025
• Heroic Axe - Warrenton, VA USA

Rally your crew for a shot at the Champion’s Trivia Belt ??! Reservations & ?? Throwing Never Required ?? Minutes from Haymarket, Gainesville, & Warr ....

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 ....

Peach and Pepper Festival at Mountain Run Winery

• Aug. 30 - Aug 30, 2025
• Mountain Run Winery - Culpeper, VA USA

Celebrate the start of Labor Day weekend and come beat the heat on Saturday, August 30st at the Peach and Pepper Festival at Mountain Run Winery! The ....

Taste of the Mountains Main Street Festival

• Aug. 30 - Aug 30, 2025
• South Main Street - Madison, VA USA

• Other / General

Madison County's small town, big festival tradition returns for its 31st year. Madison County commercial businesses and handmade crafts from all over ....