Town of Middleburg to Host Oktoberfest Celebration on September 20

MIDDLEBURG, VA — Visit the Town of Middleburg on September 20 from 11 a.m. to 6 p.m. for the town’s Oktoberfest celebration. The festivities will take place on South Madison Street and Federal Street, which will be closed to vehicular traffic. This fun-filled event will feature two biergartens, traditional German food, a stein-holding contest, live music, interactive activities for children, and much more!

Oktoberfest, including the biergartens, will open at 11 a.m. The first Oktoberfest beer keg will be delivered to the festival by horse-drawn wagon at 12 p.m. The wagon is pulled by a horse from White Hall Hounds. Middleburg Mayor Bridge Littleton will tap the first Oktoberfest keg.

In the Federal Street Biergarten, Rowdy Ace and Blaskapelle Alte Kameraden will provide the soundtrack for the day. A traditional Bavarian-style dance group will also perform throughout the festival grounds. A variety of events and performances will take place on Madison Street, including musicians and dancers. The Corgi Races return for a second year, but in a new location on Federal Street behind The Tack Box. Feats of strength will be held throughout the day, including stein-holding and other Oktoberfest games. The event will also feature a moon bounce and art activities for children.

Traditional Oktoberfest food from Little Austria Strudel, Nomad, The Preppy Pretzel, and Fields of Athenry will be available for purchase. Additional food vendors include Big Kyle BBQ, American Legion Post 295, King of Pops, King Street Oyster Bar, Raymer’s Homemade Candies, and Top Shelf Jerky. Oktoberfest beer from Lost Barrel Brewing, cider from Mt. Defiance Cidery and Distillery, and wine from Greenhill Vineyards, Cana Vineyards, 50 West Vineyards, and Boxwood Winery will also be available for purchase.

The event will feature artwork from local and regional artists, and regional craftspeople will be present throughout the day with exhibits of fine art, pottery, jewelry, wearable art, and more.

The Middleburg Oktoberfest celebration is sponsored by White Hall Hounds, Atlantic Union Bank, Tilley’s Pet Supplies, The Preppy Pretzel, and Northwest Federal Credit Union.

Oktoberfest is free to attend and features a number of family-friendly activities. Traditional Bavarian attire is encouraged, but not required. Visit middleburgvaoktoberfest.com or facebook.com/MiddleburgOktoberfest for event updates. For additional information, please contact the Middleburg Town Office at (540) 687-5152.

Posted on: September 7, 2025