MD 355 intersects MD 80 (Fingerboard Road) and passes through residential areas in the Villages of Urbana subdivision, encountering two roundabouts. Upon leaving Urbana, the route intersects Lew Wallace Street and returns to its alignment along two-lane undivided Urbana Pike as it continues north through areas of woods and farms with some rural residences.
MD 355 crosses MD 80 (Fingerboard Road) and traverses residential zones within the Villages of Urbana subdivision, encountering two roundabouts. After leaving Urbana, the route intersects Lew Wallace Street and returns to its alignment along two-lane undivided Urbana Pike as it continues north through wooded areas and farms with some rural residences.