The early roots of Reidsville, incorporated in 1873 by the State Legislature, date back to the early 19th century when William Wright of the Little Troublesome Creek area owned a tavern and store on the road connecting Danville and Salem. This outpost, called Wright's Crossroads, was the earliest settlement in the present-day city and was overseen by Wright's son, Nathan, and then Nathan Wright's son-in-law, Robert Payne Richardson. Richardson's home, built in 1842 on a knoll overlooking Little Troublesome Creek, still remains on Richardson Drive and has the distinction of being the oldest standing house in the city.