Abingdon's historic district covers 145 contributing buildings, 13 contributing structures, and 2 contributing sites - everything from a 1773 house belonging to the first settled Presbyterian pastor west of the Alleghenies to mid-twentieth-century commercial blocks. The district was added to the National Register in 1970 and expanded in 1986. The earliest layer survives in the Reverend Charles Cummings House, built around 1773, when Abingdon was still called Black's Fort. The streets themselves run along an old buffalo trace that became an Indian trade path that became a wagon road - a single corridor used by every generation of traveler the region has ever known.

General Francis Preston built the central brick block of what is now the Martha Washington Inn in 1832 as a private home for his wife Sarah Buchanan Preston and their nine children. The original Preston living room is still the hotel's lobby. In 1858 the family sold the house to become a women's college - Martha Washington College - which ran for over seventy years through the Civil War and the Great Depression. During the war the grounds served as training barracks for the Washington Mounted Rifles, and the building became a hospital for wounded soldiers, Confederate and Union both. The college closed in 1932. In 1935, in a town short on jobs, somebody decided the Preston house should reopen as a hotel.

Sinking Spring Cemetery, near the eastern edge of the district, marks where the first Presbyterian congregation in the region built a log church in the early 1700s. By 1833 they had moved to what is now the Barter Theatre building. In 1837 the congregation split, and one branch built the Greek Revival Sinking Spring Presbyterian Church that still stands on East Main Street. Across the street, the Abingdon Bank from around 1845 housed both the bank's counting room and vault and the cashier's family - a clear architectural expression of the era's idea that the man who guarded the money should sleep next to it. The same building today operates as the Fields-Penn 1860 House museum.

Most historic districts are quiet. Abingdon's is not. The Barter still draws audiences to evening shows, the Martha Washington still serves dinner in the Prestons' old dining room, the courthouse from 1868 still hears cases, and the storefronts still sell things. Walk Main Street on a summer afternoon and you pass an 1827 house, a 1913 high school, a 1851 church, and a coffee shop in a building older than the Civil War, all sharing the same sidewalk. The district works because almost nobody tore anything down. The Wolf Hill tract that surveyor Thomas Walker first marked between 1748 and 1750 is still recognizably the same place.