Festivals near Madison, VA.

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 ....

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 ....

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 ....

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 ....

??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 ....

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 ....

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 ....

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 ....

Wild West Day at Mountain Run Winery

• Aug. 9 - Aug 9, 2025
• Mountain Run Winery - Culpeper, VA USA

The winery has live music by Curt and Rob under the pole barn during the afternoon and Pauleys BBQ food truck on site starting at noon. If you want to ....

Old Town After Hours

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

• Music

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

32nd Annual Manassas African-American Heritage Festival

• Aug. 2 - Aug 2, 2025
• Metz Middle School - Manassas, VA USA

For the past 34 years, the first Saturday in August has marked the African American Culture Arts Festival in Prince William County. Over the years th ....

32 Annual Manassas African American Heritage Festival

• Aug. 2 - Aug 2, 2025
• Metz Middle School - Manassas, VA USA

For the past 34 years, the first Saturday in August has marked the African American Culture Arts Festival in Prince William County. Over the years th ....

32nd Annual Manassas African American Heritage Festival

• Aug. 2 - Aug 2, 2025
• Metz Middle School - Manassas, VA USA

For the past 34 years, the first Saturday in August has marked the African American Culture Arts Festival in Prince William County. Over the years th ....

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 ....