 Some of the roads that became segments of MD 537 were constructed in the mid-1910s as part of the original state road between Elkton and Cecilton.Other portions of MD 537 were part of the approach roads to a bridge across the Chesapeake & Delaware Canal that was built in the mid-1920s and destroyed in 1942.After the modern Chesapeake City Bridge and its approach roads were completed in 1949, US 213 was moved to the new bridge and approach roads and MD 537 was assigned to the bypassed sections of US 213.