The town was formed in 1807 and has been the county seat of Nelson County since 1809 when the courthouse was built in the center of town. The original 30-acre parcel of land on which the town sits was given by the Loving family, a very influential family over the years of the town's history. The town is dominated by the courthouse in the center of town with a grid pattern of streets surrounding it. Front, Second, and Spring streets (which are now Route 29) run in a north–south direction, while Main and Pleasant streets run in an east–west direction. The layout of the town was designed by George W. Varnum and the original design is still present today with very few alterations.
The courthouse is a significant marker of Lovingston's history as a courthouse town. It was the first public building built after the town's formation in 1807, and expansions have enabled it to remain in use to the present. Notable buildings in the square include the Whitehead Law office, the First Clerk's office, and the original jail that was based on a design from Thomas Jefferson.
Along Court Street were several taverns and hotels where people would gather to dine and rest on court days. Court days were a weekly event that would bring people from all over the county. The entire square would be filled with court attendees and their families picnicking and socializing.
The courthouse was designed by Shelton Crosthwait and is derived from the English town hall plan featuring a two-story temple front with a ground floor arcaded piazza. This design bridges the gap between colonial courthouse design and the Jeffersonian temple form.