Sixty-Something: Living Out Your Dreams on the East End

Throughout my life, I have heard the word “dream” used in many ways: dream job, dream house, dream car, dream date, and so forth. When you reach your sixties and beyond, you start making decisions to perhaps take aim and achieve some of your dreams. Over the last twenty years, I have watched so many people actualize living out their dreams on the East End. We all know the stories of dreams coming true on the East End.

Ever since there was a 1960s TV show called “Route 66,” I have desired a 1963 Corvette. Of course, at this late stage of life, I can actually buy one, I just never will. I have actually only driven in a Corvette once in my life, and disliked the ride; the same thing with Porsches and Ferraris. They ride too tight and hurt my ribcage. I find it ironic how many folks my age are now owning and driving brand new Corvettes and Porsches, realizing it’s now or never.

On the East End, I believe there seems to be a trend of successful people late in their lives who have decided to invest all their time and resources to concentrate on their dream of painting, doing photography, playwriting, or trying to finish a novel. The energy from the natural beauty of the East End seems to inspire many folks to be creative. I know I am one of those folks. In the Hamptons, it does seem normal to have a judge and a few town supervisors who, besides their jobs, just love to be up in front of people singing and playing live music all over the East End. Quite frankly, they are all talented. It’s not just local politicians who have the musical bug. Up until these last few years, billionaire Ron Perlman of Revlon had a yearly blowout party at his Wainscott estate named “The Creeks” to help raise money to support the Apollo Theater in Harlem. He would have first-rate talent from Jon Bon Jovi to Blake Shelton at these parties playing songs and performing with a huge fun jam, usually with him on the drums!

The dock in Sag Harbor in the summer has a lineup of multi-million-dollar yachts, often with a car or helicopter mounted on them. I guess for folks like Johnny Carson, having their multi-million-dollar yacht docked in Sag Harbor was a dream realized. I remember sailing one afternoon in Gardiner’s Bay and seeing a huge superyacht anchored in the middle of the bay. Suddenly, my sailing buddy Todd pointed to a helicopter in the sky, and then in total amazement, we both watched it hover over the top level of this megayacht. While this helicopter poised off the top deck, a man in a business suit with a briefcase disembarked from the helicopter and walked onto the boat as the helicopter flew away. I still have the video footage on my iPhone!

Folks have different dreams. When I was a very young man, a close friend told me while sipping a beer that his dream was to have his wife’s name on his private jet and his girlfriend’s name on his helicopter and have them shop together in Milan buying him clothes. The funny thing is this same dude has been married to the same woman for 50 years now. Funny what true love can do to dreams.

I remember a few years back the trend was to buy Bridgehampton horse farms. Madonna and Matt Lauer were two names I remember who bought horse farms in Bridgehampton in that era. I know I have often driven the back roads admiring those horse farms. They are trophy properties of the Hamptons.

I was actually assigned to cover a property being sold to the Village of East Hampton that had huge sculptures on it. At that time, Sasson Soffer, an 80-year-old world-renowned artist who lived in Amagansett and New York City, owned some wooded land off Town Road. I believe over the 19 years he owned the property, he had placed 30 of his large and small sculptures there. I actually went and inspected them. His plan was for a town-owned sculpture park that would be named Grandeland. He only wanted six of his sculptures to be the only artwork displayed. Mr. Soffer’s arts foundation was to pay for installing and maintaining the sculptures. The town bought the land in 2006. Different folks have different dreams.

I am now living out my dream of sailing, writing, reporting, and enjoying being a husband and grandfather. I am now, like so many others, living out my dreams on the East End.