In the olden days the water trade way called ‘From the Varangians to Greeks’ ran down the Lovat River through the town. Small ships were built there in those days. Trading in flax, carts, distaffs, wooden and earthenware was widely spread in Kholm.

In the 16th – 17th centuries the town was repeatedly attacked by the Lithuanians, the Poles, and the Swedes. In the late 19th century Kholm was known for crafts, including production of wooden barges and other boats.

The town was badly damaged in the Great Patriotic War.