Many New Yorkers cycle or walk Greenway Trails to include the first 3 miles of the converted 1908 Vanderbilt Motor Parkway from Cunningham to Alley Pond Parks. And while original posts and sections of the motorway are still visible, for the curious and adventurous, this forgotten history of the first concrete road built for automobiles and racing, requires further investigation.

On Columbus Day, I satisfied a quest to cycle the Vanderbilt Motor Parkway, a 55-mile bicycle adventure from Ronkonkoma and back home to Middle Village. After a train ride from the Woodside LIRR station to Ronkonkoma, I cycled the reverse 4 ½ hour journey back along much of the original route with a high temperature of 66 degrees, misty-drizzle raw, “stop peddling and freeze” morning. A hot chocolate at the onset of the ride proved pivotal. Despite a few tough hills and a-bit-too-close landscape truck or two, the trip still brought many smiles as I peddled past historic locations and even a traffic monitor that registered me at 21 mph. (OK, I was on a bit of a down-slope.)

I used Google Maps with a maximum of ten locations to force a route on or near the original. With many variations, you can create your own personal trip to make stops along the way. I tried to pick out the best worthwhile remnants. There are a few other locations that may be worth checking out on a bike trip, especially southeast of Bethpage Park, but it may be a bit more out of the way or less bike accessible. Also, traffic and getting to the start and end points of the route are a factor.

I split the map links. There is a short cut (saves a mile or two), onto a walking path (20 yards walk bike), at the end of “Schoolhouse Road” where it meets Bethpage Park to get onto the Bike Lane. Also, the “Toll Lodge” (Now the Garden City Chamber of Commerce), is not on the map and a mile backtrack to add it to a trip.

“Unlike the first roads built for commerce and horses, the Long Island Motor Parkway was conceived from a sporting contest; the colorful, exciting and often dangerous Vanderbilt Cup Races. At the turn of the 20th century the superiority of European automotive craftsmanship cast a long shadow over America’s fledgling car industry. To encourage American automobile manufacturers to challenge European quality, 26-year old William K. Vanderbilt Jr., heir to a railroad fortune and a pioneer race car driver, sponsored America’s first international road race modeled after those in Europe.”

For a complete history of the Motorway:

Here is the entire original route I worked from which was 45 miles:

Here is the route I created:
Part I

Part II