*Archival photographs are courtesy of Huntington Historical Society, and may not be reproduced in any form without their written permission*

Also known as Vanderbilt Parkway, this road was built by William K. Vanderbilt II, great-grandson of the 19th century shipping and railroad magnate Cornelius Vanderbilt. William, known as “Willie” to his friends, was a car racing enthusiast. He created the Vanderbilt Cup Races, which attracted drivers from across the globe. The open fields of Long Island seemed the ideal place to host these races until 1906, when a spectator was killed in an accident by a race car and William Vanderbilt understood the need for a safe course dedicated to racing.

Long Island Motor Parkway, built in 1908, was America’s very first expressway, running 45 miles from Fresh Meadows in Queens to Lake Ronkonkoma in Smithtown. It was the first highway to use reinforced concrete and to adopt bridges and overpasses to avoid intersections. The Parkway had 12 tollhouses, six of which were designed by renowned architect John Russell Pope, who had designed the Jefferson Memorial and the Rotunda at the Museum of Natural History in New York. The premier “limited access highway” cost $2.5 million to build and charged users a hefty toll of $2 ($45 in 2019). While the first ten miles of the highway were completed in time to stage the 1908 Vanderbilt Cup, races on this Parkway were held only till 1910, as a tragic accident that killed four spectators and injured twenty others put an end to racing on Long Island. The road then became a route for rich Manhattanites to travel to their weekend homes in the East. When cars became an increasingly popular mode of transport in the 1920s, the police-free highway took on the name of “Rumrunner's Road,” as it was used by bootleggers to deliver liquor from Manhattan to various points on Long Island.

When Robert Moses built the toll-free Northern State Highway, Long Island Motor Parkway went out of business: it was closed in 1938 and sold to New York State for $80,000 in lieu of back taxes owed by Vanderbilt. Today, remnants of the Parkway can be found as bicycle trails in county parks or lying forgotten in ruins. A part of the Parkway is still in use in Suffolk County and passes right by Half Hollow Hills High School East, reminding us of the magic of its rich and compelling history.