MD 144 begins at an intersection with MD 807 (Bedford Road) a short distance north of the Cumberland city limits. The state highway heads east as two-lane undivided Naves Cross Road, passing through a pair of ridges before meeting a pair of ramps to and from westbound I-68 (National Freeway) and heading north of a park and ride lot. Naves Cross Road continues east as MD 807A, while MD 144 turns south onto Christie Road to pass under I-68. Christie Road continues south while MD 144 turns east onto Ali Ghan Road, passing to the south of a park and ride lot. The state highway crosses Evitts Creek before receiving an exit ramp from eastbound I-68 and joins US 220 in a short concurrency. US 220 turns north onto its bypass of Bedford Road while MD 144 continues east, meeting I-68 at Exit 47, a diamond interchange.