Oktoberfest Activities, Events, and Vendors

6th Annual Middleburg Oktoberfest Celebration

September 19, 2026 - 11:00 AM to 6:00 PM

SOUTH MADISON STREET & FEDERAL STREET

Join us for our 6th Oktoberfest Celebration on September 19th from 11:00 a.m. to 6:00 p.m.! Festivities will take place on South Madison Street and Federal Street. This year we're bringing back our two biergartens, traditional German food, live music, and festival games. Local beer, wine, cider, and traditional German foods will be available for purchase from local vendors.

This year's event will also feature an Art Fair. Regional artisans will also be present with exhibits of fine art, pottery, jewelry, wearable art and more.

Food & Beverage Vendors

Lost Barrel Brewing
Boxwood Estate Winery
Greenhill Winery & Vineyards
50 West
Cana Vineyards
King Street Oyster Bar
The Preppy Pretzel
Big Kyle BBQ
Nomad
Little Austria
Field of Athenry
Top Shelf Jerky
King of Pops

Middleburg Oktoberfest Cancellation Policy

Middleburg Oktoberfest will be held rain or shine. The Festival does not have a rain date. The decision to cancel the Festival may be due to 1) inclement weather, 2) health advisory from Loudoun County or the State of Virginia, or 3) any emergency that would endanger the artists, staff, vendors or Festival attendees. The decision to cancel is at the sole discretion of the Town of Middleburg and may not be determined until the morning of the Festival. If the Festival is cancelled, every effort will be made to notify participants in advance using the contact details provided in the registration form. Refunds will be at the discretion of the Town.

For the safety of all vendors and attendees, tents must be able to withstand harsh weather and should be weighted; generally, a 40-pound weight on each tent leg is standard. Bring tarps to weatherproof your area should it be necessary. The Town does not guarantee the protection of artists/vendors goods and materials.

In the event of dangerous weather conditions (such as lightning and thunder) once the Festival has opened:

Event staff will advise you if the Festival needs to close due to adverse weather conditions.

You will need to leave your tent and find shelter in your vehicle or one of the local businesses. The Middleburg Police will maintain a presence in the area.

Town Policy is to shelter in place until 30 after the last lightning strike in the vicinity or until other adverse weather conditions subside.

If the Festival reopens, the Middleburg Police or event organizers will give the “all clear” and allow vendors and attendees to return to their places.

If the Festival must remain closed or it is unsafe to reopen, vendors will be asked to remove their tents and materials when it is safe to do so and then the street will reopen for vehicular traffic. All direction will be given by the Middleburg Police or event organizers.

Middleburg Oktoberfest 2025 Sponsors