The highway heads east-northeast as a two-lane undivided road in a nearly straight course for its entire length except for its endpoints.

MD 544 crosses Resin Creek and Foreman Branch of the Chester River and passes through the hamlet of McGinnes.

The highway crosses Pearl Creek and Red Lion Branch on either side of its intersection with MD 290 (Dudley Corner Road) south of Crumpton.

Mainline MD 544 officially ends at the highway's superstreet intersection with US 301.

[10] The first section, the portion of MD 544 from US 213 east to McGinnes Corner, was constructed as a 20-foot-wide (6.1 m) bituminous stabilized gravel road in 1946.

[1][17][18] MD 544 was reconstructed and surfaced with bituminous concrete from US 213 to McGinnes Corner in two sections between 1962 and 1964.

The Maryland State Roads Commission transferred MD 544A and the 0.23-mile-long (0.37 km) Chester River Heights Road portion of the old course of MD 544, which never received a designation, to county maintenance through a February 19, 1962, memorandum of action.