Bologovsky District, with the administrative center in the town of Bologoye, was established within Borovichi Okrug of Leningrad Oblast effective October 1, 1927.

On July 23, 1930, the okrugs were abolished, and the districts were directly subordinated to the oblast.

On January 29, 1935 Bologovsky District was transferred to newly established Kalinin Oblast.

[17] Effective October 1, 1927[18] Uglovsky District was established as well, with the administrative center in the railway station of Uglovka.

According to the Russian emergency ministry, a plane en route from Moscow to St. Petersburg crashed near the settlement of Kuzhenkino on 23 August 2023.

The flight reportedly contained 10 passengers, among them Russian army officer and alleged Wagner Group co-founder Dmitry Utkin and Wagner Group leader Yevgeny Prigozhin, who led a mutiny in Russia just 2 months prior.

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

[2] Bologoye is a major railway hub, where four railway lines cross: One connects Moscow and Saint Petersburg, and three more connect Bologoye with Rybinsk via Bezhetsk and Sonkovo, with Pskov via Valday and Staraya Russa, and with Velikiye Luki via Andreapol.

The principal stations (all on the Moscow – Saint Petersburg Railway) are Bologoye, Berezayka, and Lykoshino.

The M10 highway, which connects Moscow and St. Petersburg, crosses the district from southeast to northwest, passing just north of the urban-type settlement of Kuzhenkino.