Settlements located in the current area of Okulovsky district were first mentioned in chronicles in 1495 as belonging to Derevskaya pyatina. However, the settlement of Okulovka has only been known since 1851 and appeared in connection with the construction of the Nikolayevskaya Railway which connected Moscow and St. Petersburg. Okulovka developed first as a settlement serving the railway stations and eventually industries proliferated. It initially was a part of Borovichsky Uyezd in Novgorod Governorate. In the beginning of the 20th century, it was the administrative center of Okulovskaya Volost of Malovishersky Uyezd in Novgorod Governorate.