Best Fall Festivals in Loudoun

Bring on the alluring colors of changing leaves and the cozy feeling we get when we say hello to crisper temperatures.

The seeds of Loudoun’s agricultural heritage provide a bounty of experiences that really make a visit here memorable. Whether you love craft beer and corn mazes or artisan fairs and autumnal foliage, Loudoun has something for everyone to enjoy this fall. Since these perfect conditions last just a few short months, we like to take advantage of every autumnal activity possible.

It's time to break out the boots, hunt down all of the pumpkin-spice goodies and get ready for fall! 

Photo via @stacymichelephoto

Temple Hall Corn Maze & Fall Festival

Celebrate harvest at the farm during the remarkable Temple Hall Fall Festival featuring six weeks of autumnal adventures at their beautiful farm in Leesburg. Bounce on the giant jumping pillows, see pumpkins and corn soar through the air from the pumpkin blasters and corn cannons, watch live music or pig races and don’t forget the famous 20-acre corn maze, which presents a unique trivia challenge and theme every year. Visit the general store to buy your Halloween pumpkin and other autumnal treats!

Leesburg Animal Park's Pumpkin Village and Fall Festival

Bring the whole family to Leesburg Animal Park for their annual Pumpkin Village and Fall Festival! This exciting festival opens to the public on September 21st and is held at the beautiful animal park facility in Leesburg. The Fall Fest features giant hill slides, wagon rides, pedal carts, moon bounces, petting zoos, pony rides and so much more! Come on the weekends for live music and entertainment, face painting and give the kids a taste of flying through the air on their own zip-line.

Amazing Farm Fun Fall Festival

Ticonderoga Farms invites you to join them this September and November for their Amazing Farm Fun Fall Festival! This festival has fun for the whole family where you can hand pick your own pumpkin, go through the spooky fun zone, take a hayride through the farm, feel the wind in your hair as you travel down the hillside slide, meet and greet with farm animals at the petting zoo, test your skills in the maze and lots of other activities and fun sites for everyone to enjoy.

75th Annual Waterford Fair

The Waterford Fair is truly a fair like no other. This historic festival in Loudoun brings thousands every year to get a glimpse into what the Village of Waterford is really like. Take advantage of the opportunity to tour historic homes in the area, watch juried artisans demonstrate the techniques of traditional craftsmanship, take a tour of the Old Mill and vintage barns that have been transformed over the years into galleries for paintings and other vendors. There is something for everyone to enjoy at this year’s fair with live entertainment, children activities and more. Check the website for more information.

50th Annual Bluemont Fair

There is plenty of old fashioned fun at the 50th Annual Bluemont Fair. Head to the village September 21 & 22 for traditionally juried crafts, local art and authors, craft and farming demonstrations, live blues and country music, the children’s fair, petting zoo animals like llamas and alpacas, quilting displays, historical encampments, the return of the Indian village, wagon rides, homemade food, baking contests, local wine and beer tastings and, believe it or not, lots more! Check out their website for all of the unique fun that is going on at this year’s fair!

Fall Pumpkin Harvest Festival

All through October, make sure to visit Great Country Farms in Bluemont for their annual Fall Pumpkin Harvest Festival activities on the weekends. Make sure to heed their warning very carefully. They stress that they are “not responsible for overly happy families” and to “visit at your own risk”! It’s easy to get caught up in the fun during this unforgettable experience — picking pumpkins, cheering on the fastest piggie, getting lost in the corn maze (it’s more fun than it sounds, we promise) and meeting the regal Pumpkin Princess!

26th Annual Lovettsville Oktoberfest

Get an inside look at Lovettsville's German heritage during their 26th Annual Oktoberfest on September 28. There will be authentic German cuisine, live music, street performers, local beer and wine and so much more. Kick off the day with a pancake breakfast followed by the beer tapping ceremony. Head over to the Weiner Dog races to cheer on your favorite pup! The kids will enjoy Kinderfest with FREE games and activities. Shop your way through art, crafts, and service vendors lining the streets. Wrap up the fest Saturday night with The Reagan Years, the regions best 80's tribute band. Admission is FREE, parking is FREE, trolleys are FREE, and the all-day entertainment is FREE. Come join us in downtown Lovettsville!

October

October 4 - November 2: Shocktober at Carlheim Manor
October 5: Brambleton Fall Festival
October 12: Sweet Jazz Festival at Tarara Winery
October 12: The Virginia Fall Races
October 17 - 20: Middleburg Film Festival
October 19 - 20: Virginia Wine Festival at One Loudoun
October 19 - 20: Fall Loudoun Farm Tour
October 25: Loudoun Wine Awards at Lansdowne Resort & Spa

November

November 2: Loudoun's Largest Halloween Party at The National Conference Center