Festivals near Madison, VA.

Town of Middleburg to Host Oktoberfest Celebration on September 19

• Sep. 19 - Sep 19, 2026
• Middleburg - Middleburg, VA USA

• Other / General

The town of Middleburg will host its sixth Oktoberfest celebration on September 19, from 11 a.m. – 6 p.m. The festivities will take place on South Mad ....

Town of Middleburg to Host Oktoberfest Celebration on September 19

• Sep. 19 - Sep 19, 2026
• Middleburg - Middleburg, VA USA

• Other / General

The town of Middleburg will host its sixth Oktoberfest celebration on September 19, from 11 a.m. – 6 p.m. The festivities will take place on South Mad ....

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

• Sep. 24 - Sep 24, 2026
• 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 ....

3rd Annual Rokeby Community Festival at the Oak Spring Garden Foundation

• Sep. 26 - Sep 26, 2026
• 8538 Mill Reef Rd - Upperville, USA

• Other / General

• $1 - $10

The Rokeby Farm property has a long and storied history as an icon of the Virginia Piedmont. Operated today by the Oak Spring Garden Foundation, Rokeb ....

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

• Oct. 1 - Oct 1, 2026
• 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 in the Orchard: Wavelength

• Oct. 3 - Oct 3, 2026
• Albemarle CiderWorks - North Garden, USA

• Music

Enjoy live music by The Wavelength! The Wavelength is a consortium of Charlottesville's finest musicians. Led by vocalist/harmonica Waverly Milor, the ....

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

• Oct. 8 - Oct 8, 2026
• 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 ....

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

• Oct. 15 - Oct 15, 2026
• 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 in the Orchard: Uncle Pen

• Oct. 17 - Oct 17, 2026
• 2545 Rural Ridge Ln - North Garden, USA

• Music

Uncle Pen is a project born out of fiddler and singer Alex Caton’s lifelong love for the music of late great father of bluegrass, Bill Monroe. Togethe ....

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

• Oct. 22 - Oct 22, 2026
• 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 ....

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

• Oct. 29 - Oct 29, 2026
• 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 ....

Old Town Manassas Fall-O-Ween @ Manassas Museum

• Oct. 31 - Oct 31, 2026
• The Manassas Museum - Manassas, VA USA

• Other / General

Celebrate Halloween with the community at Old Town Manassas Fall-O-Ween on the Manassas Museum Lawn. This beloved fall tradition brings together famil ....

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

• Nov. 5 - Nov 5, 2026
• 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 ....

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

• Nov. 12 - Nov 12, 2026
• 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 in the Orchard: The Pollocks

• Nov. 14 - Nov 14, 2026
• Albemarle CiderWorks - North Garden, USA

• Music

The Pollocks are led by Jason Pollock, former guitarist and songwriter for Seven Mary Three. In the mid 1990s, Jason penned such hits as "Cumbersome" ....

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

• Nov. 19 - Nov 19, 2026
• 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 ....

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

• Nov. 26 - Nov 26, 2026
• 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 ....

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

• Dec. 3 - Dec 3, 2026
• 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 ....

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

• Dec. 10 - Dec 10, 2026
• 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 in the Orchard: Wavelength

• Dec. 12 - Dec 12, 2026
• Albemarle CiderWorks - North Garden, USA

• Music

Enjoy live music by The Wavelength! The Wavelength is a consortium of Charlottesville's finest musicians. Led by vocalist/harmonica Waverly Milor, the ....

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

• Dec. 17 - Dec 17, 2026
• 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 ....

Spotsylvania Stars & Stripes Spectacular

• Jun. 27 - Jun 27, 2026
• 9104 Courthouse Rd - Spotsylvania Courthouse, VA USA

• Other / General

Each year, Spotsylvania County hosts its Stars & Stripes Spectacular on the Saturday before July 4. Come celebrate the 250th anniversary of American i ....

Juneteenth 2026

• Jun. 20 - Jun 20, 2026
• Warrenton Aquatic and Recreation Facility - Warrenton, VA USA

Experience the high-energy Juneteenth Cultural & Arts Festival & Health Fair with vendors, food trucks, live music, stage performances, and community ....

Juneteenth 2026

• Jun. 19 - Jun 19, 2026
• Eva Walker Park - Warrenton, VA USA

Kick off the celebration with an intimate Juneteenth Block Party featuring curated vendors, food trucks, family and community history tents, a sponsor ....

Culpeperpalooza 2026

• Jun. 13 - Jun 13, 2026
• Mountain Run Winery - Culpeper, VA USA

• Other / General

• $1 - $10

We are partnering with Playdate: A Children's Museum to bring a special kids zone to the event on Saturday June 13 with activities for all kids to enj ....