The state highway heads northwest as two-lane undivided Maddox Road through a mix of farmland and forest, passing by the hamlet of Bushwood, where the highway intersects Bushwood Road.

MD 238 passes to the west of Longview Beach, a community on the Wicomico River, as the highway begins to curve to the north.

Manor Road heads east across Bull Run toward the historic home Bachelor's Hope.

The state highway reaches the community of Chaptico, where the highway passes west of Christ Episcopal Church before meeting MD 234 (Budds Creek Road) at a roundabout.

MD 238 continues east as Chaptico Road toward the community of Helen.