MD 5 begins within Point Lookout State Park in St. Mary's County by heading west on Point Lookout Road, a two-lane undivided road which continues south from the route’s southern terminus along the shoreline of the Chesapeake Bay to the confluence with the Potomac River. The route turns north, passing a fee booth for the park at the entrance before continuing into wooded areas. A short distance later, the road makes a left turn and heads northwest through a mix of woodland and farmland. MD 5 passes through Scotland and continues north through more agricultural areas with intermittent residences. It reaches Ridge, where MD 5 intersects the southern terminus of MD 235 (Three Notch Road). From here, the road heads into more wooded areas. MD 5 passes through agricultural and residential areas before turning northwest and entering St. Mary's City. Here, the route makes a turn to the north, with MD 584 looping to the west of the route through the center of St. Mary's City. The road runs along the shore of the St. Marys River and passes near St. Mary's College of Maryland before leaving St. Mary's City had heading into forested areas. It reaches Park Hall, where MD 5 intersects MD 489 (Park Hall Road).
