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

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

According to the Russian emergency ministry, a plane en route from Moscow to St. Petersburg crashed near 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.

[14] Kuzhenkino is located on the railway line which connects Bologoye with Velikiye Luki via Andreapol.