Stara Planina has a significant and special place in the history of Bulgaria since its foundation in 681. It was a natural fortress of the Bulgarian Empire for centuries and formed an effective barrier to Moesia where most of the medieval capitals were located. The Balkan mountains were the site of numerous battles between the Bulgarian and the Byzantine Empires including the Battle of the Rishki Pass (759),Battle of the Varbitsa Pass (811), Battle of Tryavna (1190) and many others. In the battle of the Varbitsa Pass, Khan Krum decisively defeated an enormous Byzantine army, killing Emperor Nikephoros I. For many centuries the Byzantines feared that mountain, and on several occasions Byzantine armies had pulled back only on the news of approaching Stara planina.
During the Ottoman rule, many haiduks found refuge in Stara planina. Close to the highest summit, Botev Peak, is Kalofer, the birthplace of Hristo Botev, a Bulgarian poet and national hero who died in the western Stara planina near Vratsa in 1876 in the struggle against the Ottoman Empire. Also close to Botev Peak is the Shipka Pass, the scene of the four battles in the Russo-Turkish War, 1877-78, which ended Turkish rule in the Balkans. Close to the pass in the village of Shipka, there is a Russian Orthodox church built to commemorate Russian and Bulgarian bravery during pass defense
