[3] The major part of the district belongs to the drainage basin of the Volga River.

[10] On 1 October 1929, governorates and uyezds were abolished, and Ostashkovsky District with the administrative center in the town of Ostashkov was established.

[10][11] On August 1, 1930 the okrugs were abolished, and the districts were subordinated directly to the oblast.

[11][12] During World War II, the district was not occupied by German troops but until 1943 stayed in the immediate vicinity of the front lines.

[15] The main agricultural specialization of the district is cattle breeding with meat and milk production.

[15] The railway connecting Bologoye with Velikiye Luki crosses the district from northeast to southwest.

This road crosses the district, and in Torzhok it has access to M10 highway, connecting Moscow and Saint Petersburg.

Ostashkov is further connected with Staritsa via Selizharovo, with Andreapol via Peno, and with Demyansk and Maryovo.

The district contains 187 cultural heritage monuments of federal significance (125 of them located in Ostashkov) and additionally 287 objects classified as cultural and historical heritage of local significance (118 of them in Ostashkov).

Other federal monuments include the Nilova Pustyn monastery, located on an island on Lake Seliger, the Novyye Yeltsy Estate in the selo of Novyye Yeltsy, as well as a number of churches in the villages of the district and several acheological sites.