MD 544 was relocated to its present course at its eastern end when the Blue Star Memorial Highway (originally MD 71 and now US 301) was built west of Millington between 1954 and 1957. The bypassed portions of the highway are now part of Chester River Heights Road west of US 301 and Legion Road (once designated MD 544A) east of US 301. MD 544 was reconstructed and surfaced with bituminous concrete from US 213 to McGinnes Corner in two sections between 1962 and 1964. The highway from McGinnes Corner to MD 290 was reconstructed in 1970 and 1971, and the remainder of the highway from MD 290 to US 301 was rebuilt in 1971 and 1972. The MD 544–US 301 intersection was transformed into a superstreet intersection in 2006, resulting in the designation of MD 544A east of the junction.