Washington Street heads south from the intersection opposite MD 245 to serve downtown Leonardtown.

The state highway immediately passes between the Leonardtown campus of the College of Southern Maryland to the east and the St. Mary's Nursing Center to the west.

[1][2] At McIntosh Road, MD 245 curves northeast through a mix of farmland and forest.

[3] The state highway was extended northeast to Hollywood in 1924 and 1925 and to its present northern terminus near Sotterley in 1925 and 1926.

[6] The state highway was rebuilt with a bituminous concrete surface from St. Johns Road to MD 235 in Hollywood in 1950 and 1951; this project included the relocation of the state highway around what is now Old Hollywood Road.