Driving Grandma: A Trip from NYC to Montauk 60 Years Ago in a Convertible Car

In 1958, when I was 18 years old, my mom and dad asked if I would drive my grandma out to Montauk. She lived in Brooklyn, wanted to visit us in what was then our new home—Dad had bought White’s Drug Store in Montauk—and as it happened at that time I had driven in to visit college friends in Manhattan, so I was available. When I picked her up at the apartment on Avenue M that sunny summer morning, she looked me up and down and asked if please I would drive carefully and not hit too many bumps on the way. She was then about 80 years old, a tiny woman and, as she said, a little delicate. She knew how an 18-year old boy would ordinarily drive. Don’t do that, she asked. I told her I wouldn’t.

The car I took her to Montauk in was the very first car I ever owned. Dad had given it to me earlier in the year when I had gotten my driver’s license. It had been his car and I had lusted after it, so when he bought a newer car for himself, he gave me this old one.

This was a 1951 Chrysler New Yorker Convertible Coupe, baby blue, with wire wheels, whitewall tires, red leather seats and a white convertible top that went up and down at the press of a button. And though 7 years old, it was in absolutely perfect condition.

Under the hood was an eight-cylinder Rocket V8 engine producing 180 horsepower capable of zooming to over 100 miles an hour—which, of course, I had never done. Yet. The front seats and back seats were both full-width upholstered bench seats. I was sure she would be happy in the front. The seat faced a rocket ship dashboard of chrome and padded leather featuring an AM radio, heater, switches and vent controls. It had a chrome button on the end of the gearshift that, when pressed with your thumb, dropped the transmission down into overdrive to pass. It also had power windows, one of the earliest cars that did. You slid a chrome toggle up and down to make the windows go up and down. No having to turn a crank to make that happen.

There were no seatbelts. They hadn’t been invented then. Wasn’t even something we thought about. Another thing was the weight of this luxurious car—nearly 5,000 pounds, it had to be gassed up every 100 miles. It got seven miles a gallon. On the other hand, gas was 33 cents a gallon.

And so the journey began. I made my way through the busy Brooklyn streets, stopping at traffic light after traffic light, and went not to the Long Island Expressway (which was still a construction project in this outer borough), but to the Grand Central Parkway, the superhighway, getting on at 224th Street. Now it was smooth sailing, at least for a while. Grandma smiled.

The big issue when driving out of the city headed for Montauk was whether to take the Southern State Parkway or the Northern State. Both were superhighways, good for grandma, but only until both of them ended, just 20 miles east of the city, at Huntington in the North or Babylon in the South. There would still be another 90 miles of driving over narrow country roads to get to Montauk. And both routes, 27 in the south and 25 in the north, took about the same amount of time. I’d take the southern route.

A little bit about Grandma. As a child, she had been brought from Lithuania to Brooklyn. There, married in 1912, she bore my mother, and later a little brother and two sisters. She talked English with a Yiddish accent. And she was very nice.

After getting permission, I turned on the radio and tuned to an early rock and roll station, 1010 on the dial, overseen by Murray the K. She swayed and hummed to the music.

I also asked if I could put the top down, and she agreed to that. I pulled into a Sunoco gas station in Babylon, right at the place where the Southern State ended to become the two-lane Sunrise Highway. Here we gassed up and I took the top down.

We drove along, frequently stopping at traffic lights on the concrete-paved Sunrise Highway, with auto dealerships and restaurants, boatyards and, at one point, a dark building called THE DOLL HOUSE, GIRLS GIRLS GIRLS. Maybe someday I’d sneak off and visit it, maybe not. Sunrise Highway was a bypass of the waterfront towns of Freeport, Babylon and Islip. But we drove through downtown Oakdale and Sayville, and saw these towns were relatively new and built on a boating and farming economy. Main Streets featured bars, clothing stores, ice cream parlors, schools, restaurants. Occasionally, rounding a turn, we’d get a view of the Great South Bay. Ferries took people to Fire Island. With the top down, the wind played through our hair. Grandma asked if we could stop at a diner for lunch, and we did.

Just past Sayville there were some big billboards. One read PATCHOGUE, LONG ISLAND’S BIGGEST SHOPPING TOWN. Another showed a row of houses and announced LIVE IN SHIRLEY HOMES NOW FOR SALE. We were approaching the end of the great wave of suburban sprawl that had rolled out from the city to there.

East of Patchogue—Patchogue was thriving, indeed—the land stretched out in great dairy vegetable and potato farms. The towns were beautiful and sturdy, with huge churches and lovely tree shaded main streets. We passed through East Moriches, then the small curving village of Eastport. Duck farms were plentiful along the narrow Montauk Highway, half on wetlands, half in shallow water. Hundreds of quacking ducks waddled about.

We stopped at one, got out of the car, and the ducks ran over to the turkey-wire fence, snapping their beaks, hoping for food. The smell of ducks was overpowering.

Soon, Montauk Highway, still a two-lane road, wended its way into the Hamptons. It acted as a bypass for downtown Westhampton Beach, went through scrub oak and then down Hill Street into Southampton Village, the first of the very beautiful and peaceful 17th century colonial towns, where the downtowns closed for business on Sundays. I knew there would be only two traffic lights now all the way to Montauk, the one at Main and Nugent in Southampton and the one at Main and Newtown in East Hampton.

Vast potato farms framed these villages. And there were more billboards. One advertised a tractor. Another read ENTERING WATER MILL, SLOW DOWN AND ENJOY IT. SPEED CONTROLLED BY RADAR. We pressed along and soon got east of Amagansett where the road dips down for the five-mile stretch run through Napeague to the hills and motels of Montauk. At the bottom of that dip onto the Napeague Stretch, 20 or 30 billboards fought for space facing us, advertising motels, fishing boats, restaurants and nightspots. Shortly, this crowd of billboards ended, and you could see the ocean everywhere, across hills and sand dunes with the road slicing through. We looked at each other. The temperature had dropped five degrees when we’d come down that hill.

I stepped on the gas. The road was straight and narrow. An occasional car passed us going the other way. Four and a half hours had passed and we were almost there, driving through sunshine and salt sea air.

As if on cue, the New York rock and roll station turned to static as the signal died. No other stations took its place.

Soon, Napeague ended, and over a hill the little shiny-new oceanfront resort motel town of Montauk where we lived appeared. We stopped at the store.

I went in and brought out Mom and Dad, and by the car everyone hugged and kissed.

“How was the trip?” Dad asked Grandma.

“He was wonderful and smooth all the way,” she said.

Dad stayed behind, but Mom, Grandma and I went home to our house on South Fairview Avenue, where my 7-year-old sister would soon be coming home from the Montauk School. Dinner would follow.