Castleton-on-Hudson, NY


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With its breathtaking scenery and deep historical roots, the Hudson River Valley is a top choice for an all-American road trip. The Dutch settled the valley 400 years ago, and even today, surnames beginning with “Van” and “Der” are abundant in this part of upstate New York.

The Hudson River Valley, a National Heritage Area, spans eight counties along the east and west banks of the Hudson River. Here, writer Washington Irving penned The Legend of Sleepy Hollow and the story of Rip Van Winkle, a fictional Dutch American farmer who slept for 20 years and awakened in a foreign, English-speaking land. The Hudson River Valley draws visitors from all around the world, as well as escapees from New York City and its suburbs.

Tarrytown and its 19th-century Gothic Revival mansion, Lyndhurst, are natural starting points for sightseeing on the eastern side. History and literary buffs will be delighted by neighboring Sleepy Hollow, which existed as North Tarrytown until its incorporation in 1996. The picturesque village’s Old Dutch Church dates to 1685 and is the oldest house of worship in New York State. Both the church and its cemetery, which Irving mentioned in his books, provided dramatic settings and the names for some of his characters.

Farther north, hike the Walkway Over the Hudson in a one-of-a-kind state park. Its centerpiece, a 1.28-mile-long, 212-foot-tall footbridge over the river, links Poughkeepsie and Highlands, New York. This converted railroad trestle is the longest elevated pedestrian bridge in the world.

The nearby village of Hyde Park is home to Springwood, the lifelong home of president Franklin Delano Roosevelt and major attraction in the Hudson River Valley. Both FDR and his wife, Eleanor, are buried on this 300-acre estate. The adjacent Franklin D. Roosevelt Presidential Library and Museum is undergoing renovation that will make it—ironically—fully wheelchair accessible for the first time since opening in 1941. The museum displays more than 1,000 photos from the Roosevelts’ private and public lives.

In Rhinebeck, north of Hyde Park, dine at the historic Beekman Arms, established in 1766, or the modern Escoffier, the Culinary Institute of America’s award-winning restaurant staffed entirely by students. Nearby, venture through aviation history at the Old Rhinebeck Aerodrome. On most weekends between June and October, the adventuresome can even fly in a vintage 1929 biplane.

The Rhinebeck-Kingston Bridge provides a convenient spot to cross to the Hudson’s western shore. The community of Kingston has some of New York’s most beautiful historic architecture. Then head south to see the U.S. Military Academy at West Point. Tours can be arranged in advance for a nominal fee. In the fall enjoy yet another great American tradition here: West Point football.

On your way back to the city, wrap up your visit to the Hudson River Valley with some serious shopping at West Nyack’s Palisades Center. A day at the eighth largest indoor shopping center in the United States, with more than 400 stores, an ice rink, two theaters, and popular chain restaurants provides a fitting end to a fine tour of Americana.