[9] In 1751, the county built a clerk's office, pillory, and prison on the eastern bank of the Nottoway River in the geographic center of Southampton.

[12] Henry Adams and Thomas Hunts purchased Lot 18 and built a house in 1796; they applied for a license to operate an ordinary there in 1797.

[12] Samuel Kello Jr., one of the original eight trustees and the Southampton County clerk of court, purchased the tavern in 1799.

[12] James Rochelle replaced Kello as clerk of court and moved into and expanded a house built in 1811 by his father-in-law on Lots 14 and 15, across Main Street from the courthouse.

[12] In August 1831, the town became well known nationally as the site of the trials and subsequent executions of Nat Turner and some of his cohorts who had planned a major slave rebellion in Southampton County[12] During the rebellion, the county's planters sought refuge in Jerusalem and the state militia used Vaughn's tavern as its base of operation.

He is better known as Confederate Major General William Mahone who served in the Virginia House of Delegates, as Petersburg mayor, and as a U.S.

[12][14] In 1853, the town was connected to Petersburg via the Jerusalem Plank Road, essentially today's Virginia State Route 35.

[10] The town was not the site of any military conflicts during the Civil War; however, troops passed through Jerusalem during the Siege of Suffolk and used Mahone's Tavern and the Baptist church as temporary hospitals.

[18] A crowd of African Americans assembled in the town for a speech by progressive politician Thomas Jefferson Pretlow on June 21, 1867.

[18] It continued to be the center of town's social gatherings, including a new tradition of a medieval-style tournament that featured colorful costumes, jousting on horseback, and a dinner and dance at the hotel.

[18] Jerusalem became a stop on the Atlantic and Danville Railway in 1888, allowing residents to ride the train to Petersburg and Norfolk for business and shopping.

[13] Postmistress Fannie Barnett suggested the name change after town residents were teased in Norfolk as being "those Arabs from Jerusalem".

[18] With the railroad, Courtland became a center for processing and warehousing agricultural produce such as peanuts and cotton from the surrounding county.

[20] The Rosenwald Fund donated $500, the county contributed $2,500, and the town's African American community raised $1,00.

[20] Courtland experienced two large fires in 1934 and 1935, damaging many historic structures and resulting in new buildings being added to the downtown commercial district.

[24] The town is the geographic center of Southampton County and the north shore of the Nottoway River that flows northwest to southeast.

Courtland is historically a town driven by the county's agriculture, especially cotton, peanuts, tobacco, and the production of hams.

[11] It encompasses 284 contributing resources and 135 acres (55 ha) in the north half of the town, along the east bank of Nottoway River, essentially running along Main Street/U.S.

Churches in the historic district are all from the 20th century and include the Gothic Revival St. Luke's Episcopal and First Baptist; the latter was originally framed but now has a brick veneer.

[17] Adjacent to St. Luke's, Courtland United Methodist was built in Colonial Revival style and has a central tower.

[17] The David Temple AME Zion was built in 1966 on the west side of town and does not follow a revival style.

[17] The one-acre Helping Hand Cemetery is located on the north side of Courtland and was opened for African Americans in 1897.

[17] This historic district also included the Mahone-Manry cemetery, a private plot behind the Seven Gables house, and a Confederate burial ground behind the Courtland Baptist Church.

[17]The Southampton County Courthouse was built in June 1834 in a modest version of the Jeffersonian Classical style.

[16] Next door to Mahone's Tavern, the c. 1820 Bell House is decorated with sawn trim and other folk Victorian elements.

[38] Also moved to its current location in Courtland, the Rebecca Vaughan House is a three-bay frame dwelling dating to c. 1790.

[38] The core of Coutland's business district consists of early 20th-century one and two-story buildings facing Main Street.

[10] The Masonic Lodge is also located along Main Street; it is a two-story frame building that dates to the late 19th century.

[10] Norfolk Southern Railway and CSX Corporation provide freight and piggyback rail services to Southampton County; the railroad junction crosses Route 58 in Courtland and runs north to south.

[49][10] The Southampton County Department of Public Utilities provides sewer service to Courtland; a waste treatment plant is located outside of the town.