An international event, it was founded by William Kissam Vanderbilt II in 1904 and first held on October 8 on a course set out in Nassau County on Long Island, New York.

Vanderbilt prevailed and the inaugural race was run over a 30.24 miles (48.7 km) course of winding dirt roads through the Nassau County area.

Vanderbilt put up a large cash prize hoping to encourage American manufacturers to get into racing, a sport already well organized in Europe that was yielding many factory improvements to motor vehicle technology.

Construction began in 1907 of the multimillion-dollar toll highway, to run from the Kissena Corridor in Queens County over numerous bridges and overpasses to Lake Ronkonkoma, a distance of 48 miles (77 km).

[3] The Vanderbilt Cup was held successfully on Long Island until 1911 when it was showcased at Savannah, Georgia in combination with the American Grand Prize.

Some of the drivers who participated in the Vanderbilt Cup became famous names, synonymous with automobiles and racing such as Louis Chevrolet, Vincenzo Lancia and Ralph DePalma.

On December 18, 1995 CART teams, convinced they were being deliberately locked out from the 1996 Indy 500, and the victims of a "power grab" by Tony George, announced their intentions to boycott that event.

The owners, along with CART president and CEO Andrew Craig, jointly announced plans for a new race, the Inaugural U.S. 500, to be held at Michigan International Speedway the same day.

[10] After the bankruptcy of the CCWS in 2008 its assets were purchased by the IRL, unifying the most prestigious level of American open-wheel racing under a single sanctioning body.