 The first portion of modern MD 298 to be constructed was the portion south of Fairlee, which was constructed as a concrete road as part of the Chestertown–Rock Hall road (now MD 20) in 1918.The highway proper was constructed as a concrete road from MD 20 in Fairlee to MD 292 south of Still Pond in 1929 and 1930.MD 298 from Fairlee to Butlertown was widened to and resurfaced with bituminous concrete in 1950.