During the dynamic reign of Ivan III (r. 1462–1505), the territories controlled by the Tsardom of Muscovy expanded significantly. Formerly independent principalities, such as Novgorod, were absorbed by mutual agreement, purchase, annexation, or conquest, adding territories to the west, north, and east. Ivan even established a port on the Gulf of Finland, providing his state with direct access to the sea. Novgorod itself had long-standing economic relations with European cities as the easternmost member of the Hanseatic League, a trading association. (Ivan III closed the Hanseatic settlement in Novgorod in 1494.)