[9] An old Severian town, Trubchevsk was first mentioned as Trubetsk in East Slavic manuscripts describing the events of 1164 and 1183, although the locally 975 is regarded as the year of its foundation.

[citation needed] At that early period, it was variously called Trubech (Трубечь), Trubetsk (Трубецк), Trubchesk (Трубческ), or Trubezhsk (Трубежск).

[citation needed] The town is referred to in the great Old Russian poem, The Tale of Igor's Campaign.

This poem calls for the princes of the various Slavic lands to join forces in resisting the invasions of the nomadic Cuman people.

Originally a minor center of Severia, Trubchevsk had its own princes sporadically throughout the Middle Ages, in 1164–1196, 1202–1211, 1212–1240, 1378–1399, and finally in 1462–1503.

[10] In the late 19th century, its inhabitants were mostly employed in flax processing and spinning, crafts, shipbuilding and trade.