In 1906, the rich and famous flocked to the Long Island Gold Coast, including a man obsessed with a new invention at the time, the automobile. William K. Vanderbilt the Second decided to launch the Vanderbilt Cup, which attracted drivers from across the country to Long Island. However, after a deadly accident, Vanderbilt invested in a main drag across Long Island just for racing - the Long Island Motor Parkway.

North Hempstead historian Howard Kroplick explains that after the deadly accident where a spectator was killed, Vanderbilt and his associates came up with the idea for the Motor Parkway. The first of its kind in the nation, the Motor Parkway stretched from Queens to Lake Ronkonkoma. Kroplick says that when it wasn't used for racing, it was a toll road.

Across Long Island there are remnants of the Parkway, including portions still used today and a bridge at Old Bethpage Village.

The Vanderbilt Cup helped launch the careers of car makers, including Henry Ford and Louie Chevrolet.