 When MD 24 was rerouted in 1933, MD 165 was extended along that highway's old routing through Pylesville and Whiteford, much of which was relocated in 1960.MD 165 begins at a seemingly arbitrary location along Baldwin Mill Road; this location was once where the highway intersected the Maryland and Pennsylvania Railroad.Baldwin Mill Road continues south as part of a series of county roads—Fork Road, Sunshine Avenue, and Bradshaw Road—that parallel Little Gunpowder Falls along the eastern edge of Baltimore County through the communities of Baldwin, Fork, Kingsville, and Bradshaw.