Lesnoye is first mentioned as Smerdyn in a birch bark manuscript found in Veliky Novgorod. The manuscript dates from the end of the 14th century or the beginning of the 15th century and is believed to refer to the same Smerdyn which later became Lesnoye. At the time, it belonged to the Novgorod Republic. In the 15th century, together with Novgorod, the area was annexed by the Grand Duchy of Moscow. It belonged to Bezhetsk Pyatina, one of the five pyatinas into which Novgorod Lands were divided.