MD 2 originally followed Armory Road through the northern part of Prince Frederick. By 1946, the highway had been relocated to its modern alignment and paved north of Armory Road to Sunderland. The bypassed portion of Armory Road was marked as MD 750 by 1950 but may have been removed from the state highway system by 1952. MD 2 was widened to and resurfaced with bituminous concrete through Prince Frederick in 1950. This improvement occurred contemporaneously with or shortly before the construction of the Prince Frederick bypass; MD 2 moved to the new wide bituminous stabilized gravel highway in the autumn of 1951. The bypass was resurfaced with bituminous concrete in 1954 and 1955. By 1956, the old road through the county seat was marked as the first section of MD 765.