[12] Settlements located in the current area of the district were first mentioned in chronicles in 1495 as being a part of Derevskaya Pyatina.

Fast economical development of the region started during and after the construction of the Nikolayevskaya Railway which connected Moscow and St. Petersburg in 1851.

Okulovsky District, with the administrative center in the settlement of Okulovka,[15] was established within Borovichi Okrug of Leningrad Oblast effective October 1, 1927.

[17] Okulovsky District was not occupied by German troops during World War II; however, being adjacent to the front line, it played an important role.

[18] Effective October 1, 1927,[2] Torbinsky District with the administrative center in the selo of Torbino was established as a part of Borovichi Okrug of Leningrad Oblast.

[17] There are three big factories in Okulovka, which produce wire, electronics, and furniture, and a limestone processing plant in Uglovka.

[19] Agriculture in Okulovsky District is represented by a number of small-scale farms, mostly involved in cattle breeding.

Okulovka is a terminal station for suburban trains, which leave in three directions: to Bologoye, Malaya Vishera, and Nebolchi.

The district has a developed road network, which includes connections to Borovichi, Tikhvin via Lyubytino, Bologoye via Lykoshino, and Kresttsy.