[2] It was built by Novgorodian merchants on a 5-kilometer (3.1 mi) portage (Russian: Волок/Volok) on a waterway from Novgorod to Moscow and Ryazan, hence the name "Volokolamsk" (i.e., "Volok on the Lama").

After the Mongol invasion of Rus', the town was divided into two parts: one assigned to Novgorod and another one to the Grand Dukes of Vladimir.

The town remained the southernmost enclave of the Novgorod Republic until 1398, when Vasily I definitively incorporated it into the Grand Duchy of Moscow.

Having lost its Hanseatic trade and connections with Novgorod, the town declined and was not mentioned by any sources for the next half a century.

In 1613, Volokolamsk braved a siege by Sigismund III Vasa, an event which led to the town's fortifications being represented on its coat of arms.

During World War II, a number of violent clashes between the German and Soviet troops and partisans took place near Volokolamsk.