Festivals near Sperryville, VA.

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 ....

??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 ....

DTFEST 2026

• Oct. 11 - Oct 11, 2026
• One Loudoun - Ashburn, VA USA

• Other / General

• $10 - $25

DTFEST 2026 – The Largest Nepali Cultural Festival in the United States Experience Nepal without leaving America. DTFEST (Dashain & Tihar Festival) ....

??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 ....

Fall Pickle & International Food Festival

• Oct. 17 - Oct 18, 2026
• 22455 Davis Dr suite #120 - Sterling, VA USA

• $1 - $10
• $25 - $50

???? Loudoun County's Pickle Festival & International Food Festival is coming back this Fall! ???? Missed the spring pickle party in April? Don’t make ....

Fall Festival by Joshua's Hands

• Oct. 17 - Oct 17, 2026
• 39550 Meadowlark Dr - Hamilton, VA USA

• Other / General

This year’s theme, “Celebrating with America!”, will set the stage for a full day of family fun, entertainment, heritage activities and community cele ....

??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 ....

??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 ....

Anime USA 2026 - Anime & Japanese Culture Convention - November 20-22 in Chantilly, VA

• Nov. 20 - Nov 22, 2026
• Westfields Marriott Washington Dulles - Chantilly, VA USA

• Other / General

• $25 - $50
• $50 - $100
• $100 - $250

Anime USA 2026 is coming to Chantilly, Virginia, November 20–22 at the Westfields Marriott Washington Dulles! For more than 25 years, Anime USA has b ....

??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 ....

??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 ....

??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 ....

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 ....

Apple Harvest Festival

• Sep. 19 - Sep 20, 2026
• Stonewall Ruritan Fairgrounds - Clear Brook, VA USA

• Arts (Arts & Crafts)
• Community (Family & Kids)
• Music
• Seasonal (Harvest)

• $1 - $10

Enjoy an autumn weekend in apple country! Vendors and Artisans, Food Trucks and Concessions,Kids Area with Inflatables, Face Painting, Pony Rides and ....

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

• Sep. 17 - Sep 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 ....

Old Town Manassas Art Show & Craft Fall Fair @ Manassas Museum

• Sep. 12 - Sep 12, 2026
• The Manassas Museum - Manassas, VA USA

• Other / General

This charming seasonal event brings together art, creativity, and community in the heart of Old Town Manassas. Browse a wide variety of handmade art, ....

National Harvest Fest 2026 Event

• Sep. 12 - Sep 12, 2026
• Tractor Supply Co. - Warrenton, VA USA

• Other / General

Join your local Tractor Supply Company store for Harvest Fest, a Farmers Market event, on Saturday, September 12, 2026. ....