Sixty-Something: My Worst Hamptons Snow Shoveling Tale

As I get older my fondness for things grows. However one thing I am never fond of is waking to have my driveway and car buried in deep heavy newly fallen snow. As a young teen I made a few bucks going around the neighborhood offering to shovel out the driveways of the older folks. Now at sixty-something I am a member of the older folks.

Before divulging into my worst Hamptons snow-shoveling tale, I will start with my first business lesson I learned that happened while shoveling an older women’s huge long driveway when I was still in perhaps 7th grade. I was living in Pelham Manor, New York where we never had town school buses to bring us to and from school. Besides that the town had a tradition back then of being the very last to close a school due to snow. However one March morning the foghorn went off all over town (pre-internet and cell phone) confirming all schools were not opening that day.

Not long afterwards our family phone rang and it was my friend Charlie Calamia calling about making some money shoveling snow. I had already shoveled my home driveway and back then at that age who ever got tired? So I trekked to his home on “the Esplanade” and we went around looking for snow-shoveling jobs. We rang doorbells and had a few quick easy jobs. We never asked how much we wanted but the folks always told us what they would give us and we would then go and enthusiastically do the job. The very last house that day was a home with a long circular driveway up a hill with the garage located around the house in the back. Even in today’s Hamptons homes era this was a big job. The elderly woman, (perhaps my age of 66 today) was so glad to see us and we never discussed a price.

This job took perhaps two hours with us going like gangbusters! When we were finished we proudly went up to the front door and rang the bell and the woman appeared extremely pleased. Then to our horror and shock she said as she opened her hand, “Here are your dimes boys!” She gave us ten cents each and shut the door.

As for my worst Hamptons shoveling story it happened one long weekend while I was staying in an East Hampton home located in the North-West Woods section. The home had a steady uphill driveway of perhaps 100 yards. It was still football playoff season although I don’t recall the exact date. I do know it was the last year that the sports bar, “The East Hampton Grille,” existed on Newtown Road in the Village before becoming Cittanuova (2003-2004).

It snowed all Friday and Friday night and I needed to get back to NYC by Monday. With plenty of groceries in the house I made a big fire in the fireplace and enjoyed being snowed in. Sunday morning I woke early and started shoveling out. I kept looking at my watch and doing travel time math as in when I might make it back to my apartment in NYC. It seemed like I was making absolutely no progress as the snow was almost literally waist high and heavy. Hours went by, and still I was lumbering on no longer dreaming of getting to the city at the hour I wanted. Then came the horror as I could see the end of the driveway and then the road. I walked the last ten yards to confirm my worst fears being realized. The road out had never been plowed and was also waist high with drifts actually over waist high. Instantly I knew there would be no drive to NYC that Sunday. I ended up walking through the deep snow all the way into the Village of East Hampton and had a hamburger and a few beers while watching a football game at the then “East Hampton Grille” sports bar. It was that day I first met J.J. Jenson, who still tends bar there (now Cittanuova) so many years later.

Sometime very early Monday the town plow trucks cleared the road and I busted out of the last ten yards and drove to NYC. Luckily my office meetings that Monday had been canceled. In NYC it took forever to find an indoor garage with space for my car.