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.


Fall Harvest and Pick-Your-Own in Loudoun


Apple Harvest at Great Country Farms

Through the rest of September, Great Country Farms' apple orchard is open for apple picking and freshly pressed apple cider tasting. Hop on the wagon to the orchard to pick ripe, delectable apples every day until the end of September - starting at 10 a.m. Mon-Fri. Weekends are for the early birds – starting at 9 a.m. Sat and Sun. Weekend picking is accompanied by live music, marshmallow roasting, pig racing and cider pressing demos. It’s everything apple, and if apples are not your choice of harvest, the pumpkin patch is also open through October. Make your fall adventure your own!


Temple Hall Farm Pumpkin Patch

Celebrate harvest at Temple Hall Farm’s Pumpkin Patch and Sunflower Fields, which are open through October. Bounce on the giant jumping pillows, participate in the farm animal scavenger hunt and don’t forget to enjoy the infamous cornbox – filled with corn not sand. Take a wagon ride to the pumpkin patch or visit the new sunflower field to pick flowers or snap a season-friendly selfie. A portion of the proceeds of pick-your-own sunflowers benefits apprenticeship programs for neurodivergent individuals at Legacy Farms, which is also on site.


Leesburg Animal Park’s Pumpkin Village and Fall Festival

Bring the whole family to Leesburg Animal Park for the annual Pumpkin Village and Fall Festival! This exciting festival opens to the public on September 21st and takes place 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 on their own zip-line.


Pick-Your-Own Pumpkin at Wegmeyer Farms

Starting September 24, Wegmeyer Farms opens its U-Pick hours from Wednesday through Sunday. Travel along the gravel path to the wonders of the Pumpkin Patch to pick from a village of pumpkins – big, small, white or orange, you’re sure to find one that suits your fancy. With more than 50 varieties, picked and unpicked, friends and family can embrace the ambience of fall. Be sure to make your reservation and journey to the farmstead to explore what the season has to offer.


Fall Fairs & Festivals in Loudoun


46th Annual Virginia Wine Festival

The 46th Annual Virginia Wine Festival will take place in Loudoun’s nightlife hotspot this year, One Loudoun. Walk into this urban town center made up of shops and eateries October 1 and October 2 to enjoy locally harvested products in the guise of wine and food – you can purchase VIP or general admission for this event. All ticket purchases include unlimited wine tastings, access to VA Oyster Pavilion, all access to concessions and all the musical performances.


78th 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’s activities and more.


Sterling Festival 2022

Melt into the crowds at the Sterling Community Center this October for Sterling Fest 2022. Explore booths offering the best of local businesses and artisans. Sample fine food from a wide variety of local restaurants. While the kids enjoy games, obstacle courses and crafts, parents can sit down in the Beer Garden for a pint of locally brewed beer or a lovely glass of Virginia’s finest wine.


Lovettsville Oktoberfest

Get an inside look at Lovettsville's German heritage during the Annual Oktoberfest September 23 to 25. There will be authentic German cuisine, live music, street performers, local beer, wine, artisans and so much more. Kick off the weekend with live 80’s music and German food trucks, followed by the beer tapping ceremony. Saturday begins with the kids 5k race and pancake breakfast and finishes with live music from the Ghost Peppers, a rock and roll cover band. To end the big weekend, brunch will be at Flying Ace Farm – admission is FREE, parking is FREE, trolleys are FREE, and the all-day entertainment is FREE.


Harry Potter: A Forbidden Forest Experience

The wizarding wonders of the Harry Potter universe is coming to Loudoun this fall. Celebrating some of the most iconic forest scenes from the Harry Potter™ and Fantastic Beasts™ films, visitors can interact with magical characters and cast their own spells, bringing the fantastical world to life through studio special effects. Enjoy delicious foods and beverages while watching the magic come to life.


More Events to Explore!



Cars & Coffee at Lost Barrel Brewing – Sept 24

Manhattan Short Film Festival – Sept 29 & Sept 30



Loudoun United end of season fan appreciation night - Oct 1

Arc of Loudoun Shocktober Haunt Party Fundraiser – Oct 8

Dining in the Dark – Oct 13

2022 Loudoun Wine Awards – Oct 14

Loudoun Farm Tour – Oct 15 & Oct 16

2022 USA Softball Pumpkin Spice Open – Oct 16

1000 Miglia Warm-Up USA – Oct 18-23

ScreamLoco - Friday, Saturday & Sunday until the end of October