Litchfield was platted in October 1853, and was originally named "Huntsville",[6] Earlier, Hardinsburg, about 2 miles (3 km) to the southwest,[7] had been founded about 1850.

[6] The railroad reached Huntsville in the autumn of 1864,[7] and within two more years Hardinsburg had substantially disappeared.

[6] The new town of Huntsville was renamed in November 1855 after Electus Bachus Litchfield, who with his brothers earlier that year had donated land and convinced the railroad of where to place its shops and terminals.

Interstate 55 runs along the western edge of the city, with access from Exit 52 (Illinois Route 16).

IL 16 passes through Litchfield as Union Avenue, leading east to Hillsboro and southwest 10 miles (16 km) to Gillespie.

[4] The city drains east to the West Fork of Shoal Creek, a south-flowing tributary of the Kaskaskia River.

[14] The Ariston Café was founded in 1924 in the town of Carlinville, Illinois, but was moved to its present location.

Another landmark is Litchfield's Lake Lou Yaeger, located northeast of town.

[15] The Sky View Theater is a member of the Route 66 Hall of Fame and has been in operation since 1950.

[citation needed] The grand opening of the Litchfield Museum and Route 66 Welcome Center was June 1, 2013.

Two Class 1 railroad lines (Burlington Northern Santa Fe and Norfolk Southern) cross at the south edge of Litchfield after running parallel through town from north to south.