Want the real country: farmland, horses, nobody in sight for miles? Head north — almost as far as you can go on the Taconic Parkway — to the town of Chatham. Spread over 53 square miles on the border between Columbia and Rensselaer counties — and about 15 miles from the Massachusetts border — Chatham is so downright cute that the Berkshires often claim it as their own. While it may be small and difficult to reach without a car (the nearest Amtrak stop is in Hudson), its primo location between Albany, New York, and Boston ensures that Chatham continues to thrive.
Founded by Dutch farmers in 1795 (Quakers followed), today Chatham consists of five hamlets. There’s a healthy mix of residents who live in the area year-round versus the ever-growing population of those who own weekend homes. “Bottom line: it’s a wonderful core community,” says Beth Hover, a real estate broker with Chatham Properties. “The people here would do anything for anybody. Tonight, there’s a spaghetti dinner at the firehouse to raise funds for a woman who’s been diagnosed with cancer.”
Like so many Valley towns, local history plays an pivotal role in Chatham’s vibe. An important railroad hub in the 19th century, the 1887 Union Station (now the home of the National Union Bank of Kinderhook) is on the National Register of Historic Places. Although the Shaker Museum — keepers of the world’s foremost collection of Shaker artifacts — recently moved from Chatham to nearby Mount Lebanon, the library remains. Lined with shops housed in 19th-century brick buildings, the village’s main drag is punctuated at one end by the pendulum clock tower, a landmark dating back to 1872 and the only one of its kind still in its original condition.
There are several notable eateries, too. At Our Daily Bread on Main Street, Zvi Cohen and sons Yoni and Gavriel offer traditional baked goods, as well as vegetarian lunch options. Down the street they opened Destino, which serves highly touted Mexican fare. The Blue Plate, a staple on Kinderhook Street, serves classic American dishes, while Lipperas’ at the Chatham House cooks up both high-end dinners and casual meals on different sides of its 1859 restored inn.
Chatham offers a good dose of culture as well. For five dollars you can catch a first-run film at the Crandell Theatre, a circa 1926 gem with cool arches and lanterns. Theatergoers can take in a show at the Ghent Playhouse; or, in the summer, at the acclaimed Mac-Haydn Theatre, which stages musical productions that often feature off-Broadway stars.
After a few years of declining sales, the real-estate market is on an upswing, says Hover. At press time, her firm had listings for an 1847 cottage with a red barn for $299,000, as well as an historic 1790 brick home for $850,000. There are many houses for as little as $150,000 to appeal to first-time homebuyers.
Population: 4,128 (town) 1,770 (village)
Median Household Income: $75,954 (town) $51,528 (village)
Fun Fact: The village of Chatham has only one traffic light, at the intersection of Routes 203 and 66.