Rhinebeck, Dutchess County, NY

Quaintly sophisticated: “Top Town” Rhinebeck, NY, is one of our best places to live in the Hudson Valley in 2012

When outsiders were surprised that the Clinton family chose Rhinebeck as the site of Chelsea’s wedding, locals simply smiled — and knew why. After all, Rhinebeck is perhaps the most sophisticated town in the Valley — with the possible exception of horsey Millbrook, which is about 20 miles to the east. Yet, with its vintage buildings and homes, the area manages to retain its historic charm.

» Read about Chelsea Clinton’s wedding in Rhinebeck, NY

First settled by the Dutch in 1686, the village is the bustling center of the town. Built in 1766, the Beekman Arms is the country’s oldest continuously operating inn. And older homes — those built prior to the 1920s — sell best, says realtor Jim Ettenson. The town of Rhinebeck includes the village as well as the 36 square miles of mostly rolling farmland beyond it. Those rural roots are showcased at local events such as the annual Dutchess County Fair (the second largest in the state), which is held at the 144-acre fairgrounds. The Old Rhinebeck Aerodrome is home to one of the world’s largest collections of vintage planes, which participate in summer air shows. Old traditions abound, too. Sinterklaas, a Dutch tradition that marks the start of the holiday season, is celebrated each year with a parade in early December.

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» See our Fall Fashion photo spread on the grounds of the Old Rhinebeck Aerodrome in Rhinebeck, NY

But Rhinebeck also has moved firmly into the 21st century. Proximity to two Amtrak train stops — in next-door Rhinecliff and Poughkeepsie — makes it easy to get to and from New York City. A sophisticated mix of stores, restaurants, and cultural attractions entice out-of-towners, who crowd the streets on the weekends.

» Click here to see the median house prices for each county (PDF opens in new window)

Interestingly, several of these businesses are run by area natives who returned to Rhinebeck after working elsewhere. Bryn Dier, for instance, returned to town with her husband — first-grade boyfriend Wesley — after he graduated from the CIA and trained as a line chef at Manhattan’s Gramercy Tavern. Their most recent venture, the Local Restaurant, is a triple entendre on the word “local.” “We’re both local, provide a place for locals and others, and emphasize local products,” Wes explains.

» Read our review about the Local Restaurant in Rhinebeck, NY

Matthew Stickle also came back to Rhinebeck to “save” A. L. Stickle variety store when his grandfather, Alfred Stickle, decided to sell it. Matthew’s wife Leah, an avid knitter, converted a back room of the store into a knitting shop. Knitting classes began there last April, creating a mini-community of its own within the village.

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Rhinebeck also holds an attraction for those with no prior connection to the area. Charles Derbyshire was tired of living in Manhattan when he spied a for-sale ad for the Old Mill Wine Shop; he bought the store, even though he had never spent a night in the village. “I thought, it’s a great little town. I didn’t even check out the school system,” he says. So comfortable is he with the easygoing atmosphere, Derbyshire says he sometimes leaves his shop open while he runs to grab a cup of coffee.

» See our profile of Rhinebeck, NY

Not surprisingly — with the increased attention Rhinebeck has been garnering in recent years — certain problems have arisen, most notably how to preserve the area’s unique character. At present, the buzz revolves around developing an events code so the village can oversee activities that attract more than 500 people. “Tourism is our strong suit,” says Mayor James Reardon. “We have to do a better job of managing traffic. And we have to grow smart.”

County: Dutchess
Population: 7,548 (town) 2,657 (village)
Median Household Income: $67,284 (town) $61,125 (village)
Fun Fact: During the 1890s, the cultivation of violets became a booming industry that eventually earned Rhinebeck the moniker of the Violet Capital of the World. Local cinematographer Tobe Carey’s documentary Sweet Violets premiered in February. See the May issue for more about the film and Rhinebeck’s purple past.

» Return to Top Towns 2012

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