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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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September 2018

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View map »


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More information

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Cost: free

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Sponsor: Litchfield Farmers Market
Telephone: (860) 000-0000
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More information

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Cost: free

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View map »


Sponsor: Loft Gallery at The Smithy
Telephone: 860-868-9003
Contact Name: Susan Newbury
Website »

More information

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View map »


Sponsor: New Morning Market
Telephone: 203-263-4868
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More information

Joan Morosani and Susan Spencer are excited and honored to be showing together for the third time at OWL. They draw from different approaches and traditions, but feel that their paintings perfectly...

Cost: Free

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View map »


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Telephone: 860-567-8030
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Cost: Free

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View map »


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Telephone: 212 255 6247
Contact Name: Steven Miller
Website »

More information

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View map »


Website »

More information

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Cost: FREE

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View map »


Sponsor: Hunt Hill Farm
Telephone: 860-355-0300
Website »

More information

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Where:
Washington Art Association
Gallery 4 Bryan Memorial Plaza
Washington Depot, CT
View map »


Website »

More information

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Cost: Free

Where:
Gunn Memorial Library
5 Wykeham Road
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View map »


Sponsor: Gunn Memorial Library
Telephone: 186-086-87586
Contact Name: Sharon Morrissey
Website »

More information

Show More...
Show Less...

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129 Main St North
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View map »


Sponsor: New Morning Market
Telephone: 203-263-4868
Website »

More information

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Cost: Free

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View map »


Sponsor: Oliver Wolcott Library
Telephone: 860-567-8030
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Website »

More information

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New Morning Market
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View map »


Sponsor: New Morning Market
Telephone: 203-263-4868
Website »

More information

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Cost: free

Where:
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West & Woodruff Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Farmers Market
Telephone: (860) 000-0000
Contact Name: Kay Carroll, Market Master
Website »

More information

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Where:
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View map »


Sponsor: Hunt Hill Farm
Telephone: 860-355-0300
Website »

More information

The Loft Gallery welcomes an exhibit of large-scale landscape and gardenscape paintings by South Kent CT artist, Lisa Brody. This show opens on Saturday, September 1st, and runs through Sunday,...

Cost: free

Where:
Loft Gallery at The Smithy
10 Main Street
New Preston, CT  06777
View map »


Sponsor: Loft Gallery at The Smithy
Telephone: 860-868-9003
Contact Name: Susan Newbury
Website »

More information

Scott Bond is pleased to announce three events to be celebrated with an opening reception on Friday August 24 from 6-8pm at “Byrde + the b” a full service hair salon, art gallery and...

Cost: Free

Where:
Byrde + the b
10 Titus Road
Washington Depot, CT  06794
View map »


Sponsor: Byrde + the b
Telephone: 212 255 6247
Contact Name: Steven Miller
Website »

More information

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Where:
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58 N Lake St
Litchfield, CT
View map »


Website »

More information

Opening Reception: August 11, 4-6pm. This event is free and open to the public. MAQUETTE: The Art of the Model is an exhibition of maquettes or models by many of the sculptors currently...

Where:
Washington Art Association
Gallery 4 Bryan Memorial Plaza
Washington Depot, CT
View map »


Website »

More information

Washington Photographer Philip Dutton’s dramatic photos document The Chief Bigfoot Memorial Ride of 1990, a momentous event that helped commemorate the 100th anniversary of the Massacre at...

Cost: Free

Where:
Gunn Memorial Library
5 Wykeham Road
Washington, CT  06793
View map »


Sponsor: Gunn Memorial Library
Telephone: 186-086-87586
Contact Name: Sharon Morrissey
Website »

More information

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Cost: FREE

Where:
Center School Parking Lot
Woodruff Lane
Litchfield, CT  06759
View map »


Telephone: 860-567-3871
Website »

More information

Show More...
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