At the southeastern edge of Poughkeepsie is Vassar College (124 Raymond Ave., 845/437-7000, www.vassar.edu) founded as a women’s college in 1861 by the brewer Matthew Vassar, at the instigation of his friend Samuel Morse. Considered a risky experiment at the time, Vassar today—now coeducational—is recognized as one of the best colleges in the country.

Surrounding much of the campus are towering stone walls with arched gates. Inside is the 1865 Main Building—reputedly designed in such a way that it could be converted into a brewery should the educational experiment fail—and a Norman-style chapel with five Tiffany windows. One of the windows depicts Elena Lucrezia Cornaro Piscopia, the first woman to receive a doctorate (from the University of Padua in 1678).

Near the main gate stands the Frances Lehman Loeb Art Center (124 Raymond Ave., off Rte. 44/55, 845/437-5632, http://fllac.vassar.edu, 10 a.m.–5 p.m. Tues.–Sat., 1–5 p.m. Sun., free admission), designed by Cesar Pelli. Vassar was the first college in the country to have its own art gallery, and today owns more than 12,500 works ranging in origin from ancient Egypt to modern-day New York. Especially strong are the collections of Hudson River landscape paintings, Old Master prints by Dürer and Rembrandt, and contemporary European and American art.