The first locality in the current area of the district, the selo of Urdom, was mentioned in the chronicles in 1323.

[11] On 12 July 1929, governorates and uyezds were abolished, and Oleninsky District with the administrative center in the settlement of Olenino was established.

[13][14] On August 1, 1930 the okrugs were abolished, and the districts were subordinated directly to the oblast.

[12][13] During World War II, in 1941—1943, the district was occupied by German troops.

[14] On 12 July 1929 Molodotudsky District, with the center in the selo of Molodoy Tud was created as well.

On March 5, 1935 Chertolinsky District with the administrative center in the selo of Chertolino was established.

[10] The main agricultural specializations of the district are cattle breeding with meat and milk production, as well as crops, flax, and potato growing.

[10] The railway which connects Moscow and Riga via Rzhev, crosses the district from east to west.

The M9 highway connecting Moscow with Riga also crosses the district, passing Olenino.