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The city was founded by the Slavs. As a town, Brest – Berestye in Kievan Rus – was first mentioned in the Primary Chronicle in 1019 when the Kievan Rus took the stronghold from the Poles. It is one of the oldest cities in Belarus.
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In 1409 it was a meeting place of King Władysław II Jagiełło, duke Vytautas and Tatar khan under the archbishop Mikołaj Trąba initiative, to prepare for war with the Teutonic Knights. In 1410 the town mustered a cavalry company (banner) that participated in the Polish-Lithuanian victory at the battle of Grunwald.
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In 1566, following king Sigismund II Augustus decree, a new voivodeship was created - Brest Litovsk Voivodeship. After it became part of the Polish–Lithuanian Commonwealth in 1569, it was renamed Brest-Litovsk.
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On September 19, 1794 the area between Brest and Terespol was the scene of a victorious battle won by the invading Russian Imperial army under Suvorov over the Kościuszko Uprising army division under general Karol Sierakowski (known in Russian sources as the Battle of Brest). Brest was annexed by Russia when the Poland-Lithuania Commonwealth was partitioned for the third time in 1795.
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In March 1918, in the Brest-Litovsk fortress on the western outskirts of Brest at the confluence of the Bug River and Mukhavets Rivers, the Treaty of Brest-Litovsk was signed, ending the war between Soviet Russia and the Central Powers and transferring the city and its surrounding region to the sphere of influence of the German Empire.
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On June 22, 1941, the fortress and the city were attacked by Nazi Germany on the first day of the anti-Soviet Operation Barbarossa. Thus, in the summer of 1941, the Germans had to capture the city yet again, this time from the Soviets. The Brest Fortress held out for six days. Abandoned by the Soviet army, nearly all its defenders perished. The Germans placed Brest under the administration of the Reichskommissariat Ukraine.
