The area was settled in the prehistory, and, as the Western Dvina always has been an important waterway, there are multiple archaeological sites in the district. The fortress of Porechye () is first mentioned in 1499, and since 1514 it belonged to the Grand Duchy of Moscow, at the border with the Grand Duchy of Lithuania. In 1580, after the Livonian War, the area was transferred to Poland, where it was included into Vitebsk Voivodeship. In 1667, according to the Truce of Andrusovo, it was transferred back to Russia. Subsequently Porechye developed as an important trading post since it was located at the intersection of roads connecting Saint Petersburg with Kiev and Moscow with Riga. The Kasplya was navigable until mid-19th century, and Porechye sent ships to Riga. Later, it lost its trade important, since the Kasplya became more shallow, and the railway between Moscow and Riga went via Velikiye Luki, far from Porechye.