The largest county in Virginia, Pittsylvania County consists of 982.89 square miles. Situated in the south-central Piedmont plateau region, the land is rolling to hilly with elevations averaging from 400 to 800 feet above sea level. The highest point in the county is Smith Mountain, which is 2,043 feet high.

The county borders North Carolina and is adjacent to the City of Danville. Chatham, the county seat, is 140 miles from Richmond, 68 miles from Roanoke, 50 miles from Lynchburg, and 96 miles from Raleigh, North Carolina.

The county was formed in 1767 from Halifax County and assumed its present boundaries in 1777. It was named for William Pitt, First Earl of Chatham, a British Statesman who served as Prime Minister of Great Britain from 1766 to 1768.