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Car Island: The Intersection of Automobile and Long Island History

Between the hours of 7 and 9 a.m. and 5 and 7 p.m., the Long Island Expressway becomes the East Coast’s largest parking lot. That’s not a verifiable fact, but anyone who has endured a work day on LI can relate to spending hours in bumper-to-bumper traffic. And while there’s probably a similar situation on every major highway, LI’s history and that of the automotive world’s have crossed paths in the past.

The Vanderbilt Cup started in 1904 and was the first trophy awarded for auto racing in America. The annual race was held near the home of its namesake, William Kissam Vanderbilt II, in Nassau County on a 30-mile course. In its third year, a spectator was killed, prompting the race to be shut down. That was until…

Vanderbilt Motor Parkway was built in 1908 by William Kissam Vanderbilt, father of the Vanderbilt who started the Vanderbilt Cup, as a means to continue the race. To solve the safety issues which ended the Cup, the road was constructed with bridges and overpasses to remove all intersections.


James Glickenhaus’ coach-built P4/5, which cost upwards of $4 million.

Want to go back to the future? PJ Grady is a DeLorean dealership in West Sayville. The family-owned dealership first sold Chevys in the early 1900s. The shop now specializes in restoring and maintaining the iconic ride, offering parts and services to bring it from the ’80s to present day. PJ Grady was also featured on a Japanese show called New York Style as well as The Early Show on CBS.

The .2-mile loop known as Islip Speedway operated from 1947 to 1985 was the smallest track to host NASCAR’s Grand National Series. In 1958 it entered the history books and car insurers’ worst nightmares when it hosted the first official demolition derby. The Speedway was also the site of ABC TV show Wide World of Sports throughout the early 1960s.

In an episode of The Sopranos, the Riverhead Raceway was sold. The scene caused enough confusion that LIers started calling the track to ask if it was true. Ultimately, the Raceway’s owner put a sign up informing passers-by the track hadn’t changed hands.

Long Island Cars is a car show that has been running for more than 30 years at notable LI venues like North Hempstead Beach Park and Belmont Racetrack. The show is chock full of meticulously restored and detailed vintage and exotic cars, and if you’ve got an extra spot in the garage, the Car Corral for owners willing to part with their classic rides.

With the closing of Islip Speedway in 1984, Riverhead Raceway is the only racing venue on the Island. It started being built in 1949 and opened as a dirt track two years later. In 1955 the track was paved and laid as asphalt. The Raceway hosts the Whelen All-American Series and Whelen Modified Tour, and has six divisions for its races: Modified, Super Pro Truck, Blunderbust, Late Model, Figure Eight, and Charger.

Film director and stock market whiz James Glickenhaus owns a one-of-a-kind custom built Ferrari P4/5 by Italian custom car maker Pininfarina. The P4/5 is based on already extremely rare Ferrari Enzo, and was commissioned as a one-off by Glickenhaus and Ferrari. The car reportedly cost upwards of $4 million, including the donated Enzo. His private collection also includes a host of other antique Prancing Horses, a Ford GT and Alfa Romeo 8C Competizione.

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