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Housatonic River, river in southwestern New England, rising in the Berkshire Hills, near Pittsfield, Mass., U.S. It flows southward for 148 miles (238 km) through Massachusetts past Pittsfield, Lee, and Great Barrington; and then through Connecticut past New Milford, Derby, and Shelton to enter Long Island Sound, 4 miles (6 km) east of Bridgeport. Several hydroelectric plants utilize the river’s drop of 959 feet (292 m) in the first 119 miles (191 km) to Derby....