Fall Festivals Happening in Hunt Country
Written by Emerson Leger
Old Bust Head’s Harvest Festival
Get in the fall spirit with live music, a new beer release, food trucks, and all things autumn on September 20 at Old Bust Head. There will be a “pick-your-own” pumpkin patch and pumpkin painting, and baby goats will be on-site. Don’t miss this crisp and cool way to start the season. The festival will also include an artisans’ market full of fall finds. “This year is going to be even bigger than previous years, with over a dozen vendors,” shares Old Bust Head’s marketing and events manager.
Harvest Festival
7134 Farm Station Road
Warrenton, VA 20187
Middleburg Oktoberfest
Middleburg Oktoberfest is celebrating its fifth anniversary this fall, so come out to celebrate on September 20 from 11 a.m. to 6 p.m. Experience traditional German food and games and shop from local vendors. Coming back again this year is Artist’s Alley, where local and regional art will be available for purchase.
Hang out in town for a couple hours and experience a taste of Germany!
Middleburg Oktoberfest
S. Madison and Federal Street
Middleburg, VA 20117
Loudoun Heritage Farm Museum’s Heritage Harvest Festival
Calling all apple lovers! From apple-themed games and mocktails to cider pressing, the Heritage Harvest Festival is a fresh take on the beloved apple festival. It will take place on September 27 from 10 a.m. to 4 p.m. General admission is $10 and free for members of the museum and children 2 and under.
Celebrate the season with a day of fall fun in Sterling, Virginia.
Heritage Harvest Festival
21668 Heritage Farm Lane
Sterling, VA 20164
Bluemont Fair
The Bluemont Fair is an old-fashioned country fair in the foothills of the Blue Ridge Mountains. Located in Bluemont, Virginia, it’s been held every fall since 1969. This year, it will open to the public the weekend of September 20 and 21.
“You really have to experience the fair to truly appreciate the length and breadth of the talent and creative magic this tiny village creates each year,” Deb Snyder, a publicity spokesperson for the fair, says.
Enjoy pony rides, live bluegrass music, food, and a special Children’s Fair. Hours are 10 a.m. to 5 p.m. each day.
Bluemont Fair
33846 Snickersville Turnpike
Bluemont, VA 20135
Waterford Fair
The Waterford Fair will take place October 3 through 5 in the heart of historic Waterford. Situated in Virginia wine country, the fair will feature local artisans, guided tours of historic homes, and live entertainment. It will be open daily from 10 a.m. to 5 p.m. and all ages are welcome. Come for the lively music, history, and fun that has been offered since 1943.
Waterford Fair
40222 Fairfax Street
Waterford, VA 20197
Middleburg Film Festival
This prestigious festival will take place in downtown Middleburg from October 16 through 19. Founded in 2013, it has featured a wide variety of actors and directors, from Emma Stone and Sterling K. Brown to Greta Gerwig. Both documentaries and narrative films will be screened in various locations across town, with Q&A sessions with filmmakers, actors, and directors to follow.
Head over to Middleburg to experience Hollywood in Hunt Country and enjoy a different type of movie night.
Middleburg Film Festival
300 W. Washington Street
Middleburg, VA 20117
Lucketts’ Fall Market
Named one of Southern Living’s best antique shows in the South, Lucketts’ Fall Market is celebrating 25 years this fall. Tickets are on sale now for this huge event happening October 17 through 19.
Over 200 vintage vendors from the East Coast will be in attendance. With live music, food trucks, workshops, and all the vintage finds you can imagine, this market has something for everyone. Come shop till you drop at Lucketts this October.
Lucketts’ Fall Market
890 W. Main Street
Berryville, VA 22611
Hume Day
For those seeking a more traditional experience, visit Leeds Ruritan Park on Saturday, September 13, for a jousting competition going back 50 years and an apple pie contest with cash prizes up to $50. Hosted by the Leeds Ruritan Club, all proceeds help fund scholarships for graduating seniors at Fauquier County schools. The event will be held from 10 a.m. to 4 p.m. with the jousting taking place at 1 p.m., and admission is free. Hume Day also includes games and activities for kids, over 20 local vendors to shop from, a pork barbecue lunch, raffles, and more. Be sure not to miss this small-town gem! ML
Hume Day
12032 Hume Road
Hume, VA 22639
Featured photo by Jennifer Jule Studios.
Posted on: September 4, 2025