Touted as the first international road race in America, the very first Vanderbilt Cup Race took place in 1904 on Long Island. William K. Vanderbilt Jr. proposed the 28-mile race and donated the first Vanderbilt Cup for the winner.
The above photo, taken in 1956, captures two long-gone eras in one shot. Titled “Riding Out of the Past” the description says, “a bewildered contemporary driver watches as a couple driving an antique auto drive past in the Vanderbilt Cup Race in Westbury, Long Island.”