The highway runs 7.29 miles (11.73 km) from MD 290 in Chesterville north to Belchester Road in Kentmore Park.

The portion of the highway south of Locust Grove was removed from state control in the late 1980s but returned with an extension to Chesterville in the early 1990s.

The highway has a grade crossing of the Chestertown Branch of the Northern Line of the Maryland and Delaware Railroad before reaching MD 213 near Locust Grove.

[3][4] That segment was one of several state highways whose construction as 9-and-16-foot-wide (2.7 and 4.9 m) concrete roads was partially funded by a $900,000 Kent County bond issue in 1929.

[11][12][13] MD 444's present course on the west side of Locust Grove was built in 1968; the highway north to Kentmore Park was resurfaced with bituminous concrete the same year.

[18] The 0.30-mile-long (0.48 km) portion of Morgnec Road had been constructed as part of the original MD 447 in 1929 and 1930, another beneficiary of the 1929 Kent County bond issue.