[10] The district is located in the southern end of the Valdai Hills, on the divide separating the drainage basins of the Baltic and Caspian Seas.

The Tsna and the Lonnitsa are technically inflows of the Vyshny Volochyok Reservoir, which has two outflows, one into Lake Mstino and the Msta, and another one into the Tvertsa River.

Some areas in the southwestern part of the district belong to the drainage basin of the Poved River, a right tributary of the Tvertsa.

The area of the district was populated since prehistoric times, as is witnessed by a large number of archeological sites.

It was located on one of the most popular waterways between Baltic and Caspian seas, which followed the Msta, the Tsna, and the Tvertsa.

On April 2, 1772 Vyshnevolotsky Uyezd of Novgorod Governorate was established, with the seat in Vyshny Volochyok.

Vyshnevolotsky District, with the administrative center in Vyshny Volochyok, was established within Tver Okrug of Moscow Oblast.

During World War II, the district was not occupied by German troops, but it was located close to the front line.

As of 2012, the district held the third position in Tver Oblast in terms of the number of pigs.

The federal monuments are the canals of the Vyshny Volochyok Waterway, the Afimyino Estate in the selo of Afimyino, the Borovno Estate in the selo of Borovno, as well as a number of churches, houses, and archeological sites.