Drissa is first mentioned in a chronicle of the year 1386. During the medieval period it formed part of the Principality of Polotsk, the Grand Duchy of Lithuania, and the Polish–Lithuanian Commonwealth. From 1801 it was the center of the Drissa uyezd of the Vitebsk Governorate, and during the War of 1812 it was the site of a fortified camp described by Leo Tolstoy in Book Three of "War and Peace".