MD 53 begins at an intersection with US 220 (McMullen Highway) in Cresaptown. Winchester Road continues south as a county-maintained highway toward Pinto. MD 53 begins as a one-way street headed southbound. The state highway becomes two-way at its intersection with Brant Road, which joins the one-way street southbound. MD 53 receives northbound traffic from US 220 via MD 636 (Warrior Drive). Southbound traffic approaching the intersection of MD 53 and MD 636 may use either state highway to access both directions of US 220. MD 53 continues north from MD 636 as a two-lane undivided road that crosses Warrior Run. MD 53 continues north along the western flank of Haystack Mountain, crossing Winchester Run a few times and intersecting both ends of MD 951 (Vine Street), the old alignment of MD 53. The state highway expands to a four-lane divided highway as it passes to the west of Country Club Mall. After an intersection with MD 658 (Vocke Road), MD 53 turns northwest and passes under I-68 (National Freeway), with the only direct access an entrance to eastbound I-68. The state highway then meets its northern terminus at an intersection with US 40 Alternate in La Vale. Access to westbound I-68 is provided a short distance to the east on US 40 Alternate.