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NYC to Hudson: about 130 miles
Why go: Hudson boasts great antique shopping at stores like Keystone, which specializes in 19th-century Americana, like a chestnut dining table that started out as a Civil War army cot. On the way, Dia:Beacon offers world-class contemporary art and Kaatsbaan (an estate that once belonged to Eleanor Roosevelt's grandparents) features international dance performances.
Where to stay: Built in 1854, the Rhinecliff hotel in Rhinebeck recently underwent a five-year renovation; each room now features a private balcony with spectacular views of the Hudson River (doubles from $239).
What to eat along the way: In Tarrytown, star chef Dan Barber prepares stunning, high-end tasting menus at Blue Hill Stone Barns, using ingredients that come from the farm right outside the restaurant's windows; for Hudson dining, there's Mercato, known for its house-made pastas.