First mentioned in 1150, it was established as a fortress defending eastern approaches to Smolensk. In 1508, Vasily III sent Italian masters to build a wooden fort there. Dorogobuzh was ravaged during the Time of Troubles, with its population reduced to ten people in 1614. Between 1611 and 1668, it belonged to Polish–Lithuanian Commonwealth as a part of Smolensk Voivodeship. Subsequently, it survived other foreign invasions and numerous fires.