A local tradition dates the town's origins to 937. Uglich had been the seat of a small princedom from 1218 until 1328 when the local princes sold their rights to the great prince of Moscow. As a border town of the Grand Duchy of Moscow, it was burned several times by Lithuanians, Tatars, and the grand prince of Tver.
Grand Duke Ivan III of Moscow gave the town to his younger brother Andrey Bolshoy in 1462. During Andrey's reign, the town was expanded and first stone buildings were constructed. Particularly notable were the cathedral (rebuilt in 1713), the Intercession Monastery (destroyed by the Bolsheviks) and the red-brick palace of the prince (completed in 1481 and still standing).