In 1771 Chatham County was carved out of Orange County and the first county courthouse was built just south of what would become Pittsboro. On January 6, 1787, the North Carolina General Assembly authorized nine commissioners to purchase one hundred acres and the Town of Pittsborough was formed as the seat of Chatham County. The town was named for William Pitt the Younger, second son of the Earl of Chatham who had long defended American rights in the British Parliament.
Based on a Lancaster square plan, one hundred twenty five lots were laid out surrounding a public square bisected by four streets. Surrounded by inns and taverns, the public square was the central gathering place of the town and the county. "Courtweeks" became the social and commercial highlight of the calendar. County justices of the peace ruled on local cases and the crowds produced an open market for farmers, peddlers of jewelry, dry goods and medicines as well as itinerant actors, musicians and medical practitioners.