The highway heads east as two-lane undivided 2nd Street through the South Chesapeake City Historic District.

After crossing Back Creek, the highway makes a right-angle turn at the entrance to the Chesapeake & Delaware Canal Museum, which includes the Old Lock Pump House.

MD 286 leaves the town limits of Chesapeake City and passes along the southern boundary of the Bethel Managed Hunting Area.

Shortly after the intersection with Bethel Cemetery Road, which leads to the eponymous burial ground, the highway reaches its eastern terminus at the Delaware state line.

[1][15] In their post–World War II planning request, Cecil County's top priority was rectifying the lack of connection of MD 286 to Delaware.

[18] 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.

[20] This block of Bohemia Street was part of the original route of the Cecilton–Elkton state road through Chesapeake City, with its northern end curving east and feeding into the bridge across Back Creek.