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Poughkeepsie sits on the Hudson River about 75 miles north of New York City, in the stretch of valley that Washington Irving, Frederic Church, and Thomas Cole immortalized in the 19th century as the defining American landscape. The city itself has had a rougher 20th century than its riverfront setting would suggest, losing population and industry after the mid-century IBM employment boom faded, but it has been rebuilding around culture and its most spectacular asset: the Walkway Over the Hudson. Opened as a pedestrian bridge in 2009 on the skeleton of a railroad bridge from 1889, it is the world's longest elevated pedestrian bridge at 1.28 miles, connecting Poughkeepsie to Highland on the west bank with views up and down the river that make it one of the finest walks in New York State.

Vassar College, founded in 1861 as one of the first women's colleges in America and now coeducational, occupies a 1,000-acre campus just east of downtown with a Frances Lehman Loeb Art Center that holds a surprisingly strong collection including works by Rembrandt and Homer.

The Bardavon 1869 Opera House on Market Street is the oldest continuously operating theater in New York State. Franklin D. Roosevelt's family home, Springwood, is about 8 miles north in Hyde Park, and the Eleanor Roosevelt National Historic Site and the Vanderbilt Mansion are all within easy driving distance, making Poughkeepsie an efficient base for Hudson Valley history.