The famous Mille Miglia vintage car rally arrives from Italy

Racing legends from Europe and the United States are back on the road. The Mille Miglia is coming to America. One of the world’s most renowned motor races, the original Mille Miglia was held almost every year from 1927 to 1957. Competitors tackled a 1,000-mile loop linking Brescia, Bologna, Rome and Milan. Italian marques like Alfa Romeo, Maserati, Lancia and Ferrari—and the Italian drivers who raced them—dominated the event, but famous foreign brands such as Jaguar, Porsche, BMW and Mercedes, along with a handful of American makes, also took part.

After a couple of spectacular—and fatal—accidents in the late 1950s, the race was discontinued. It was reborn in the late ’70s as a vintage-car gathering along a similar route. Restricted to vehicles that had competed in, or would have been eligible for, the original races, it now embraces hundreds of cars, including classics valued between five and eight figures.

For the first time, a spin-off edition (150 miles) will be held in the United States from October 25 to 27, winding through the horse country of Virginia and Maryland surrounding Washington, D.C. A gala will be held at the Italian ambassador’s residence, Villa Firenze—a Guggenheim family villa in Rock Creek Park.

“This is the first event our organization will hold outside Italy,” says Francesca Parolin, general manager of 1000 Miglia Srl. “It’s all part of the broader strategic plan our board has set in motion: a global expansion of the Mille Miglia brand.”

Entry requirements mirror the Italian version. Exclusive entries are open to vehicles that would have been eligible to race in the mid-20th-century Mille Miglia. But there’s a twist: a focus on celebrating American cars.

“For the second Italian Mille Miglia in 1928, the winner of the inaugural race drove a Cadillac and took his class,” says Mark Gessler, president of the Historic Vehicle Association, a nonprofit working with the U.S. Department of the Interior and the Library of Congress to preserve and promote American automotive heritage. The association is a key partner in the American 1000 Miglia. “Ford V-8s ran in the Mille Miglia during the ’30s. Even one of the early Ford Thunderbirds raced in the mid-’50s.”

This first American 1000 Miglia includes many of the noted European marques but also features several important American cars—and you’ll see even more in years to come as the field and race distance expand. Here are some of the most remarkable and valuable of the dozen-or-so entries set to compete at the end of October.