[2][3] It was created in 1842 from Harlan and Perry counties,[4] and named for Robert P. Letcher, Governor of Kentucky from 1840 to 1844.

[5][6][7] The area now known as Letcher County was first settled in the early–1800s by the Caudill, Dixon, Stamper, Collier, Lewis, Whitaker, Wright, Craft, Brown, Halcomb, Holbrook, and Bentley families.

The first permanent settlement in the county was settled in 1803, at the mouth of Pert Creek, in modern-day Whitesburg.

[10][4] The state government commissioned members of the general assembly to draw the boundaries for the new county.

The debate was settled when Stephen Hiram Hogg donated his land in Whitesburg for the building of the courthouse.

It was demolished in 1897 due to its failing condition and Lemuel R. Perry was commissioned to construct a replacement.

The new courthouse was built of bricks, and had a large cupola, with a bell inside to call the jury into session.

This new courthouse was heated by stoves and fireplaces until an addition was built in the late–1930s, by the Works Progress Administration.

By the 1960s, the courthouse was deemed too small, and prisoners in the jail on the top floor would often escape by pushing apart the bars, climbing out the window, and sliding down a rope of bedsheets.

[13] Harry M. Caudill's 1963 book, Night Comes to the Cumberlands: A Biography of a Depressed Area, brought the county to national attention.

The CBS documentary Christmas in Appalachia (1964) hosted by Charles Kuralt also brought the nation's attention to Letcher County as citizens sent clothes and gifts in response to the conditions of those featured.

[14] On March 9, 1976, in the community of Oven Fork, an explosion caused by coal dust and gasses occurred at the Scotia Mine, resulting in the deaths of 15 miners.

[18] On September 19, 2024, then-County Sheriff Shawn Michael (Mickey) Stines was arrested for shooting and killing District Judge Kevin Mullins in his chambers.

[22] Fishpond Lake is a 28.8 acres (11.7 ha)[23] man-made body of water near Jenkins, in Payne Gap, Kentucky.

In an effort to bring tourists to Letcher County and to revitalize the local economy, the Pioneer Horse Trail was constructed on Pine Mountain.

[26] Documents obtained by the Lexington Herald-Leader under Kentucky's Open Records Act showed that construction actually began before the study was to take place.

County-owned bulldozers started clearing trees in part of a wildlife management area in which heavy equipment was not permitted.

Fish and Wildlife Service to determine if any species on the threatened or endangered list were harmed.

[44] The schools located in the district are: {Letcher County has a somewhat similar political history to West Virginia.

[51] However, with increasing unionization under the New Deal it turned for the next sixty to seventy years into a fairly solid Democratic county, apart from the 1956 and 1972 landslides and the candidacy of John F. Kennedy.

However, since 2004 as the Democratic Party has become opposed to coal production due to global warming issues, it has become a solidly Republican county.

[55] Letcher County is part of Kentucky's 5th congressional district, represented by Republican Hal Rogers.

[56] Letcher County is part of Kentucky's 29th Senate district, which is represented by Republican Scott Madon.

[57] Letcher County is part of Kentucky's 94th house district, represented by Republican Mitch Whitaker of Fleming-Neon.

The Commonwealth attorney has the ability to prosecute violations, and present evidence to a grand jury.

[62] The sheriff has the responsibility to collect taxes, election duties, provide service to courts, and enforce laws.

The sheriff was Democrat Mickey Stines until his arrest for murder in September 2024 and subsequent resignation.

The circuit court deals with civil issues, capital offenses, felonies, land disputes, and probate cases.

The circuit court has the ability to dissolve marriages, hear cases of child custody, visitation, distribution of property, adoption, and parental rights.

[74][75] The Letcher County Community News-Press is a weekly newspaper located in Cromona, near Fleming-Neon, that has been in operation since 1988.