As many autophiles know, the Bridgehampton area is steeped in racing history. Beginning in 1915, the Firemen sponsored street races as part of their summer carnival. Those races ran laps over a rectangular course that included Main Street, Halsey Lane, Paul's Lane, and Ocean Avenue. Homemade and modified cars piloted by local drivers like John Ambrose, Moosie Thompson, Court Rodgers and Norris Hopping put pressure on visiting racers as they reached speeds of up to 50mph. These early races continued through 1921.

Racing revived in 1949 when Bruce Stevenson, inspired by the first Watkins Glen race in 1948, organized a similar event in Bridgehampton. Predominately European racing cars reached speeds in excess of 100mph on a 4 mile road course that ran on the roads of Bridgehampton and Sagaponack. 1953 saw both the last Bridgehampton race and the end of open road racing in New York State . However, during those 5 years the likes of Briggs Cunningham, Tommy Cole, George Huntoon, Fred Wacker, the Collier brothers, Bob Grossman, John Fitch, radio and TV personality Dave Garroway and many others raced at Bridgehampton in the greatest races of the era, before crowds up to 50,000 spectators.

In 1957 the soon to be world famous Bridgehampton Race Circuit opened on 500 acres of open land just north of the village. For over 35 years races of international importance took place on its winding course. It was acknowledged to be one of the best circuits in the world by renowned drivers such as Mario Andretti, Phil Hill, Walt Hansgen, Pedro Rodriguez and Dan Gurney. The last major event ran in 1970, but the track continued to provide great racing for later amateur and budding professional drivers and spectators for another 20 years.
In 1993 Jeffrey Vogel and the Bridgehampton Historical Society organized the first Vintage Sports Car Road Rally to commemorate and keep alive the hamlet's racing history. Although the high-speed thrills of the earlier races cannot be recreated, our rally keeps the spirit of competition alive in Bridgehampton at legal and safe speeds on the highways and twisty back roads of the picturesque area from Montauk through Southampton.  
Today our rally is a non-timed leisurely tour throughout our scenic and historic community. The route uses public roads complete with local traffic and includes stops at historic sites and related trivia questions. Entrants must be adept at driving and map reading to participate.

Although initially only cars which could have competed in the original Bridgehampton Road Races were eligible,  our invitation now extends to cars made before 1970.  Some exceptions may be made for later models of “special interest”. If you are interested in participating, please see our "Contact Us" tab.