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Middleburg Cup & Street Festival

10.21.2022 @ 4:30 pm - 8:00 pm

Iconic Italian Car Rally Returns to Middleburg!

The 1000 Miglia is coming back to Middleburg from October 18 to 23 with the official race happening on October 20-22. Old Ox Brewery will be open…

Friday, October 21: Middleburg Cup & Street Festival
Starting at 5:00 p.m., the Town will host the Middleburg Cup, where participants will race head-to-head in a regulatory race to see who can cross the finish line as closely to the prescribed time as possible. (This isn’t a speed race – it’s a precision timing race.) Using a single-elimination knockout format, each car will vie to be the winner in a precision race that may be determined by mere thousandths of a second.

This race will take place on Madison Street, starting at the Pink Box and ending at Old Ox Brewery. (Traffic will be controlled by the Police Dept. at the intersection with Route 50.) The public is encouraged to line the route along Madison Street and cheer on your favorite car!

Following the head-to-head race, all the cars will be parked along Madison Street, where a FREE Street Festival will take place. Visitors can walk around the cars, taking a look at these amazing vintage vehicles. In addition, food trucks and merchandise will be available for purchase. Be sure to grab your 1000 Miglia hat, polo, or jacket – and stop by for the opportunity to purchase some unique 1000 Miglia memorabilia straight from Italy!

Want to learn more? Check out more details here!


4:30 pm - 8:00 pm
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Old Ox Brewery Middleburg
(540) 326-8943
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Old Ox Middleburg
14 S. Madison
Middleburg, VA 20147 United States
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