The highway runs 2.43 miles (3.91 km) from MD 213 east through Chesapeake City to the Delaware state line in southern Cecil County.

The first section parallels the north side of the Chesapeake & Delaware Canal; this portion was constructed around 1930.

The highway was paved as a 18-foot-wide (5.5 m) concrete road from Lock Street to the Delaware state line between 1928 and 1930.

[3][4][5] The Lock Street portion of MD 285 was constructed over multiple steps and assigned multiple designations as part of the Cecilton–Elkton highway, which was one of the original state roads the Maryland State Roads Commission designated for improvement in 1909.

[6] The portion of the highway from Elkton to the north town limit of Chesapeake City, including both segments of Hemphill Street and the stretch of MD 285 between them, was constructed as a 14-foot-wide (4.3 m) macadam road between 1911 and 1914.

[16] However, the portion of MD 537B from US 213 to the north town limit was returned to state maintenance through an August 22, 1961, road transfer agreement.