In their post–World War II planning request, Cecil County's top priority was rectifying the lack of connection of MD 286 to Delaware. Their wish was fulfilled when the state received the link of Bethel Road between Bethel Cemetery Road and the state line in a July 1, 1947, road transfer agreement and promptly paved it. The Bethel Cemetery Road portion of MD 286 was transferred to county control in a May 8, 1958, road transfer agreement. The western end of MD 286 achieved its present form through a December 22, 1965, road transfer agreement between the state and the town of Chesapeake City. The state transferred the of highway on 3rd Street and Bohemia Street to the town, and the state took control of on the block of 2nd Street between George Street and Bohemia Street. MD 286 was resurfaced with bituminous concrete along its entire length in 1976, and the highway's bridge across Back Creek was replaced in 2002 and 2003.