 MD 5 crosses into Charles County, where it continues north on Leonardtown Road through areas of rural residences. The route reaches Hughesville, where MD 5 bypasses the community to the east on a limited-access highway and MD 5 Bus. (MD 625) continues to the north through Hughesville on Old Leonardtown Road. The bypass heads through wooded areas before coming to a dumbbell interchange with MD 231 (Prince Frederick Road) that features roundabouts where the ramps meet MD 231. Past MD 231, the bypass continues through woodland before intersecting MD 5 Business again. From here, MD 5 heads northwest through a mix of woods and farms with some residences and businesses. The route turns to the west and passes through Bryantown, where it intersects Olivers Shop Road / Bryantown Road intersection.
