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.

[6] The portion of the highway from Elkton to the north town limit of Chesapeake City was constructed as a 14-foot-wide (4.3 m) macadam road between 1911 and 1914.

[8] At that time, the main highway from the north used Knights Corner Road, Elk Forest Road, and Spears Hill Road, entered Chesapeake City 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, from which the highway followed Basil Avenue toward Cecilton.

[1][12][13] After the tanker Franz Klasen' destroyed the vertical lift bridge on July 28, 1942, the Maryland State Roads Commission established a ferry service across the canal.

[3] 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.

[1][5] The remainder of MD 537B not maintained by the U.S. Army Corps of Engineers was transferred to Chesapeake City in 2015.