One of Russia's oldest cities, Smolensk derived its name from the resin [Rus., smola] extracted from the surrounding pine trees. The city was already a commercial center in the late 9th cent., when it was the capital of the Krivichi tribe and a fortress and settlement for traders and artisans. It then fell under Kiev's rule. Its control of the key portages between the Dnieper and Western Dvina rivers gave Smolensk its early strategic importance. It also lay astride the trade route from the Baltic to Constantinople; Smolensk was connected with the Black Sea by the Dnieper and with the Hanseatic cities of the Baltic Sea and with Moscow and Novgorod by some of the most important medieval trade links. The city declined in the 11th cent. but revived in the 12th cent. to become the capital of an independent Belarusian principality. Smolensk was sacked by the Mongols in 1238–40.

The westward expansion of the grand duchy of Moscow made Smolensk a target of prolonged struggle between Moscow and Poland-Lithuania. It was captured by the Lithuanians in 1408, taken by the Russians in 1514, occupied by the Poles in 1611, and reconquered in 1654 by the Russians, to whom it passed by the Treaty of Andrusov (1667). Its location on the main route from Moscow to Warsaw made Smolensk a target for Napoleon I, who seized the city in Aug., 1812, after a brief but heroic resistance. Having burned Moscow, Napoleon retreated in November to Smolensk but was forced by the Russians under General Kutuzov to continue his retreat.

The city, scene of some of World War II's heaviest fighting, was captured by the Germans in 1941 and retaken by Soviet troops in 1943. Virtually razed, Smolensk was rebuilt with its original pattern largely preserved. Historic buildings now restored include the famous kremlin and town walls (1596–1602), the Uspensky Cathedral (1677–79), several 12th-century churches, and monuments to Kutuzov and to the composer M. I. Glinka.