10 Top Towns

Settled by the Dutch, Quakers, or Huguenots, nestled in the Catskills or on the river’s banks — these 10 Valley communities all have one thing in common: They’re great places to call home



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red hookThe laid-back village of Red Hook is home to the Merritt Bookstore Vol. II, as well as several fine restaurants

Photograph by Michael Coddington

Dutchess County

Red Hook

Until the 1800s, the Village of Red Hook was called Hardscrabble; one surmises it was not exactly Xanadu West. Certainly there was not much about Hardscrabble that suggested a metamorphosis into such a charming little village.

Red Hook is both a Town and a Village, with the former also comprising a number of smaller hamlets, among them Tivoli; Barrytown, site of the Unification Theological Seminary; and Annandale-on-Hudson, the home of Bard College (and the place Steely Dan claims they will never go back to in their hit “My Old School”).

With the studious tone set by its institutions of higher learning, Red Hook is renowned for its academics — its public school system is arguably one of the best in the Hudson Valley. The schools include “a music department that is second-to-none, and performing arts activities that rival much larger districts,” says David Temple, a classical guitarist who has lived in Red Hook for eight years. The high school is one of only a handful in the Hudson Valley to offer an International Baccalaureate diploma.

Said to be one of the state’s oldest formal organizations, the Red Hook Society for the Apprehension and Detention of Horse Thieves still holds an annual meeting

Tourists come to visit Bard College and the Aerodrome in nearby Rhinebeck, but the locals soak up the beautiful views of the Hudson River, promenades along Poet’s Walk, and ice cream cones at Holy Cow. The vibe, Temple says, is low-key and collegial. “I like the combination of small town aspects — I shop in the village IGA where I can talk to the butcher himself and buy local produce — and New York sophistication. I have attended and performed in concerts at the Bard’s Fisher Center,” he says.

When locals desire a little more action, Red Hook’s big cousin Rhinebeck is just five miles south. Here, chichi shopping, fine dining, and a popular independent movie theater draw hordes of tourists on weekends throughout the year. Still, there are several notable eateries in Red Hook, too. Mercato’s standout Northern Italian fare and casual atmosphere ensure it is perennially packed, and Max’s Memphis BBQ has a well-deserved reputation as one of the best barbecue joints in the region. But it was the addition of the sophisticated Flatiron Steakhouse in 2008 that really raised the dining bar in town.

Town Facts:

Location: Northern Dutchess County
Population: 11,500 (T), 1,900 (V)
Median Household Income: $47,000
Nomenclature: According to local lore, Dutch navigators exploring the Hudson River happened upon Cruger’s Island — which is actually a peninsula, or hoek in Dutch — in the autumn, when the foliage was a brilliant red.
Notable residents: Margaret Hamilton, the actress best-known as the Wicked Witch of the West; fiction writer Robert Sheckley

» Next stop: Pawling, Dutchess County

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