George Middleton/Louis Glapion House, 5 Pinckney Street

Pinckney Street was built as a dividing line between the North and South sides of the Hill. Joy Street, originally called Belknap Street, which runs perpendicular to Pinckney, is the only street, besides Charles, that connects the two slopes. Pinckney Street was primarily a working class street and home to mostly wood frame houses in the late eighteenth-early nineteenth centuries.

Five Pinckney is the George Middleton/Louis Glapion House. Built around 1787, it is the oldest house on the Hill that was built and owned by African Americans. It was built as a double family home with two entrances. Glapion was a hairdresser and Middleton was a jockey and a horse breaker by profession, and he also served as a Colonel in the Revolutionary War.