In Europe, all roads may lead to Rome, but on the east end all roads lead to Route 27. If you are traveling out to the south fork of the east end from up-island, you can get everywhere from Route 27. It hasn’t always been that way.
It was back in the mid-1920s that a road was designated to go from the edge of NYC (Queens) to Amagansett. Robert Moses had a dream of an elevated Highway right through the Hamptons. Imagine that with exits for fast food, gas, and rest areas. Of course, it didn’t happen.
Everyone out east has a Route 27 story. Whether it was being stuck in traffic for hours, or viewing an accident, or seeing a huge boat, home, or railroad bridge come rumbling by. My most recent delay experience was watching President Trump’s motorcade leaving Southampton. It was quite a spectacle of police motorcycles, police cars, special SUVs, ambulances, military vehicles, two Presidential limousines…in all it was over 100 vehicles. As the huge, very long motorcade passed, all the other cars could not move!
The first time I drove a car on 27-E, it was with Jim Chiusano and Barnes McNevin, back in the summer of 1970. I was seventeen. The car was my aqua-blue 1969 Ford Maverick. We had no maps, just advice from Barnes’s sister, Katie, to find the Sunrise Highway and take it east. When we reached Southampton, we headed for the ocean. Quite frankly, even though we were all from posh Westchester County, we never saw estates as we did on our way to the ocean beach off Meadow Lane. We ended up sleeping under the stars on the dunes off what is now Dune Beach. Most likely illegal at the time, but back then who knew? We were 17 years old. That eventful night there was no wind, and we were attacked by one thousand gnats!
Of the many stories I have done over the years, the story of Felice Lupo is the quintessential Route 27 story of all time. In 1971 Mr. Lupo, a former Italian policeman, came to America, leaving his family behind until he established himself. He got a job making pizzas in Brooklyn and eventually he saved enough money to bring the family over to the U.S.
When they arrived, he took them for their first drive in America, a ride east on Route 27! When they reached Amagansett, they were hungry, so they stopped at a pizza place. Back then the pizza parlor in Amagansett was located a few doors east of the Talkhouse. The owner began to tell Mr. Lupo he wanted to sell the business as he was preparing the pizza for Mr. Lupo’s family. As Mr. Lupo told me, before they were done eating, Lupo made the deal to buy the business.
Sadly, on August 8, 2014, Felice Lupo passed away. He was 88 years old. His family eventually sold the business. It was all because of a family ride on Route 27.
If you live in the Hamptons, your objective on most trips is to avoid the summer weekend or weekday rush hour traffic of Route 27 whenever possible. However, in the off-season when I traverse the Hamptons by car, I still enjoy driving Route 27, viewing favorite landmarks such as the forever view east heading into Montauk or coming down the hill going west. Then there is quaint Amagansett Village. Next comes the historic Hook Windmill, followed by the charming East Hampton Village with the South Cemetery elbow turn towards Southampton. I always enjoy entering Bridgehampton. Remember when the Rogers Mansion was in ruins? Now it looks wonderful.
Finally, the James Corwith Grist Mill in Water Mill lets me know the truly scenic part of my drive west on 27 is about to become very commercial in nature. I always get a kick seeing the Parrish Art Museum before that sudden turn. I still remember first reporting about the plans to build it.
When there is zero traffic cruising down 27 is pleasant. Quite frankly, you can get to anywhere from Route 27 in the Hamptons.