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.
In 1881 a new brick courthouse was built in the square for $10,666. The Classical Revival brick edifice is elevated on a raised basement and is topped by a three stage cupola. It was restored to its original appearance in 1991 and functions as the aesthetic heart of Pittsboro's Historic District. The district spans 59 acres and lists 92 principal buildings, 39 outbuildings, and 3 cemeteries.
At the turn of the century the business district began to evolve from frame buildings to fire resistant brick store fronts. The historic architecture of Pittsboro remains an important visual reminder of the town's growth since the late eighteenth century.