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Playland

Where the rich & famous ( and families) serve and volley



Dinesh Rajagopalan with tennis enthusiast Gene Wilder, Indian tennis star Raghu Ponnuswamy, and Leonard Ripley of Stamford.

Litchfield County has long been a draw for New Yorkers wanting weekend and summer getaways to the forests, fields, lakes and hills. But for some, the main attraction, starting 50 years ago, was the New Milford Racquet Club, a little hub where celebrities and wealthy Manhattanites would gather for friendly competition and camaraderie. Designer Oscar de la Renta moved to Kent, and the violinist, Isaac Stern, to Gaylordsville, in large part because of the five red clay courts that were installed by tennis pro Clarke Downey in 1965.

Bridgewater billionaire Peter May and his wife, Leni, were regulars there, as was the fashion designer Diane von Furstenberg, and actors like Robert Redford and Gene Wilder would pop in for a pickup match when they were in town.

“This was back before anyone had tennis courts in their backyards,” says Warren Weiss, a retired New York attorney who, with his wife, Jane, was among the earliest club members and kept playing there until last year. “My youthful appearance belies the fact that I’m getting older, so it came time to quit. That place was one of the highlights of my life.”

Weiss remembers volleying frequently with then-future New York Governor Eliot Spitzer. “He was a teenager, and we’d go out and hit around.” He also enjoyed matches with Isaac Stern. “Isaac didn’t move so well. He was a much better violinist.”

Alex Fisher and his wife, Enid, of Roxbury, were also disciples of the club for more than 40 years. “It was the absolute social focus of the area,” he says. “Everyone loved it. There were some really outstanding players, and some members who didn’t play tennis at all. It was a place everyone wanted to be. You could forget all your cares there.”

By 1972, a 36-foot-by-71-foot pool was installed, and the club was renamed the New Milford Tennis & Swim Club. It changed hands several times before being bought by Susie Kupersmith in the late 1970s. (She later married and became Susie Kilberg.)

“I’ll tell you, those were the days,” says her husband, George Kilberg. “Susie put everything she had into that place.”

After the clay courts flooded on opening day, she replaced them with six courts made of Har-Tru, a gray-green crushed stone with great drainage. “Now, suddenly, no one had to wait to play after it rained, which was great, because everyone knows New Yorkers don’t like to wait,” quips Mr. Kilberg, 84, from his Florida home.

Dinesh Rajagopalan bought the club in 1997. He had been the number-six ranked player in India, and in 1990 was recruited by Ivan Lendl to work as head pro at his club in Banksville, New York. He has since added a children’s camp and a pickle ball court—a sport that is also enjoying its 50th anniversary and soaring popularity.  

The club is a favorite retreat for local families, too, like the Ezras, who live down the road and have been members for seven years. “This place is like a built-in play-date, every day,” said Kathleen Ezra last summer as she watched her nine-year-old son Aiden land a giant cannonball off the diving board. “I seriously don’t know what we’d do without it.”

Ezra and her three sons are at the club “pretty much every day, all day, in summer. The boys are either swimming, playing tennis, pickle ball, or handball, or raking the courts for a free milkshake at the snack bar,” Ezra says. Her husband, Jason, plays tennis on weekends and comes after work to join friends for cocktails around the pool. “It’s the most amazing group of people here; everybody’s nice and there is zero snootiness.”  

As the club continues to grow and prosper, with over 100 families and 150 individual members, Rajagopalan wants to hold on to its glorious past while moving it into the future. “I want bubbles on the tennis courts so we can play in winter. I see a brand new, expanded pool. This is my dream come true, and it’s ever-evolving.”

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