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Weston: Fairfield County’s Best-Kept Secret

It is a picturesque town located among Fairfield County’s most idyllic ones. It would be the perfect location for a Norman Rockwell rendering of a small town – if that small town had residents such as Keith Richards and Christopher Walken walking its tree-lined streets.

Yes. Weston, Connecticut, is all that.

And it was proclaimed by Connecticut Magazine as the No. 1 town in the entire state for a population of 10,000 to 15,000.

Located about an hour from New York City and adjacent to Westport, its shoreline-hugging sister, Weston is not your typical New England hamlet. In addition to the famous Rolling Stone and the infamous actor, Weston’s celebrity residents include – and have included – Christopher Plummer, Robert Redford, Tom Cruise, Jose Feliciano, Eartha Kitt, Donna Summers and James Naughton. And, of course, the ongoing rumor persists of Johnny Depp’s alleged residency.

Its population is small – 10,000 – but its zoning is a generous 2 acres. And 20 percent of Weston’s residents commute to Manhattan each day.

For those who spend the better parts of their days in Weston, the town offers a profusion of benefits, chief among them are its schools. Top rated in Connecticut, the Weston public school system (lower, middle and high school) is centrally located in town in a campus-like setting.

“It’s a great place to raise children,” said resident Gail Sagel. “The schools are like private schools. Just look at some of the colleges the kids get into: University of Pennsylvania, Dartmouth, University of Michigan, Emory, Yale and Harvard … and the list goes on.”

According to Sagel, life in Weston is something of a throwback to a more simple time. “On Saturday and Sunday mornings, I love the small-town feeling of running into neighbors while shopping for fresh fruits, vegetable and pies at the farmers’ market on Route 57, right by the church.”

Sagel also takes in the town's natural beauty when she hikes the pristine trails that snake through one of its nature preserves, Devil’s Den. And she enjoys the sweeping views from the reservoir at the top of Valley Forge Road.

For a small fee, Weston residents are eligible to use some of the facilities in Westport, namely Compo Beach and Long Shore Golf Club. And Westport’s shopping and train station are only a few minutes away.

As to the local celebrities, longtime Weston resident Donna Gordon fondly recounts the following tale: “When my son Jeremy was in elementary school, he participated in the end-of-year field day. All the parents came to watch their kids participate in the festivities — relay races, sports, etc. Keith Richards' daughter was in Jeremy's class. The games started pretty early, and most of the parents were sipping their coffees. But not Keith Richards. He was drinking beer.”

You won’t see that in any Norman Rockwell paintings.

Interested in buying a home in Weston? Take a look at this property, offered by the Higgins Group Westport.

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