Festivals near Madison, VA.

2025 Via Colori® Stafford Street Art Festival

• Sep. 27 - Sep 27, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

What: 5th Annual Via Colori® Stafford Street Art Festival When: Saturday, September 27 - Sunday, September 28, 10:00-5:00 both days* Where: Stafford R ....

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 ....

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

• Sep. 25 - Sep 25, 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 ....

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 ....

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 ....

Community Day Fun

• Sep. 20 - Sep 20, 2025
• Lifesong Community Church - Mineral, VA USA

Join us for a community fair with free food (including Brunswick stew), games, and entertainment. Enjoy a day of laughter, time together, and communit ....

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 ....

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 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 ....