All of MD 286 except for the eastern and western ends was constructed as a concrete road between 1928 and 1930. The original route was L-shaped; instead of the highway continuing into Delaware, the highway turned north onto Bethel Cemetery Road to the old village of Bethel, which was alternately known as Pivot Bridge. The western end of MD 286 included two blocks of the original state road between Cecilton and Elkton, which was paved as a concrete road within Chesapeake City in 1915. The state road entered Chesapeake City from the north along Hemphill Street, crossed the Chesapeake & Delaware Canal on a one-lane bridge, turned west and crossed Back Creek on a wooden bridge, turned south onto Bohemia Street in South Chesapeake City, turned west onto Third Street, and turned south onto George Street to the south end of town.