Vytegra was first mentioned in 1496 as Vytegorsky Pogost. Since 1710, it was known as the village of Vyangi (?????) at the confluence of the Vytegra and the Vyangi Rivers. In 1773, it was granted town status and renamed Vytegra. It was an important transit point for cargo, which lied at the crossing of a waterway connecting central Russia with Lake Onega and a road connecting Saint Petersburg and Arkhangelsk. In 1715, a shipyard was founded by Tsar Peter the Great on the Vytegra River upstream from Vyangi. The shipyard was in operation until 1847. The idea to build a canal connecting the river basins of the Neva and the Volga was already discussed by Peter, but the canal, formerly the Mariinsky System, was only built in the beginning of the 19th century. In the 20th century, it was reconstructed and renamed into the Volga�Baltic Waterway.
In the course of the administrative reform carried out in 1708 by Peter the Great, Vyangi was included into Ingermanland Governorate (known from 1710 as Saint Petersburg Governorate). In 1727, it was transferred to the newly established Novgorod Governorate. In 1773, Vyangi was renamed into Vytegra was chartered, and in 1776 Vytegorsky Uyezd was established as one of the uyezds of newly established Novgorod Viceroyalty. It became a part of Olonets Oblast.
A sequence of administrative reforms followed. In 1781, Olonets Oblast was transferred to Saint Petersburg Governorate, and in 1784, it was transformed into an independent administrative unit, Olonets Viceroyalty. In 1785, Vytegorsky Uyezd was abolished and merged into Pudozhsky Uyezd. In 1799, Olonets Viveroyalty was abolished and divided between Novgorod and Arkhangelsk Governorates. Vytegorsky Uyezd returned to Novgorod Governorate. In 1801, Olonets Governorate was established, and Vytegorsky Uyezd became one of several uyezds of the governorate.
In 1922, Olonets Governorate was abolished, and Vytegra was transferred to Petrograd Governorate (later