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. In the 1920s, the
U.S. Army Corps of Engineers widened, straightened, and deepened the canal. As part of their work, the agency constructed a
vertical lift bridge across the canal. Between 1924 and 1926, the
Maryland State Roads Commission constructed approaches to the new bridge on both sides of the expanded canal, eliminating two narrow and dangerous bridges and four right-angle turns in Chesapeake City. The new route along George Street became part of
U.S. Route 213 (US 213) in 1927. The two blocks along 3rd Street and Bohemia Street became the western end of MD 286. After the tanker
Franz Klasen destroyed the vertical lift bridge on July 28, 1942, the U.S. Army Corps of Engineers constructed the present
tied arch Chesapeake City Bridge and new approach roads to the bridge between 1946 and 1949. US 213 was moved to the new Chesapeake City Bridge, leaving behind MD 537C on George Street. 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. ==Junction list==