The eastern end of US 302 was formerly at Longfellow Square in Portland, Maine. The highway follows a 19th-century stagecoach road from Portland through Windham to Bridgton. The portion from Windham to Bridgton was built about 1785. Stagecoach service began in 1803, and the route became a post road for the United States Postal Service in 1814. Transportation over this route was augmented by the Cumberland and Oxford Canal from 1832 to 1932, and by the Bridgton and Saco River Railroad from 1883 to 1941. The highway through Crawford Notch follows the Tenth New Hampshire Turnpike built in 1803 and parallels the Maine Central Railroad Mountain Division built in 1877. The highway eliminated railway passenger travel over the route from Portland by 1958, and railroad freight service through Crawford Notch was discontinued in 1983.