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Battle of Monastyryshche - a battle during the Khmelnytsky Uprising, which took place on March 20-21, 1653 near the town of Monastyryshche. The Cossack detachment led by Ivan Bohun managed to stop the advance of the Polish-noble army led by Stefan Czarniecki, who was carrying out a new punitive campaign against the Cossack Hetmanate.

At the time of the Battle of Monastryshche in the spring of 1653 , there were about 2,500 Cossacks under the command of Ivan Bohun. Taking into account the spring roadlessness, flooding of rivers and streams, as well as the considerable distance between hundreds, as well as diseases and other important reasons, the Cossacks of the Kalnytskyi regiment did not have the physical opportunity to arrive at the assembly points on time. Under such critical conditions, Ivan Bohun was able to gather only the nearest hundreds of Cossacks. It was not for nothing that the Polish magnate Stefan Czarnecki was considered one of the best generals of the Polish-Lithuanian Commonwealth. Being quite a strategist, he predicted these circumstances in advance. Therefore, the corps led by him advanced almost unhindered along the "Black Path" through the territory of the Kalnytskyi regiment in March 1653.

The noble armored banners of the Commonwealth of Independent States numbered more than 15,000 nobles, soldiers and German Landzknechts, i.e. well-trained hired professional troops, as well as more than 10,000 train servants and well-armed servants. This 25,000-strong Polish punitive corps, using the tactics of mobile cavalry units, moved along the "Black Way" in an extremely rapid march from Northeast Volhynia. In order to terrify the Cossacks, Stefan Czarniecki gave the order to plunder the territory "with fire and sword". Men and women, children and old people were brutally tortured, hanged and impaled. Property was looted, homes were burned... Flying Polish units destroyed small Cossack outposts and fortified towns. Thus, the small Cossack fortresses of Samohorodok, Pohrebyshche, Pryluka , Lypovets and many other Cossack villages and farms were burned to the ground . Colonel Ivan Bohun learned about the mass advance of the enemy through his territory already when the Poles were practically "on the doorstep" of the regimental town of Kalnyk .

There was no time for meetings, because in early spring almost all Cossacks were at home. Caught by surprise, Colonel Ivan Bohun sent messengers to the hundreds closest to Kalnyk to block the advance of Polish units on the Black Road to Uman . According to the alarm, only three hundred Cossacks of the Kalnytskyi regiment were gathered : the Kalnytsky , Balabaniv and Terlytsky hundreds and the Tsybulivsky hundred of the Umansky regiment, that is, together about 400 Cossacks. Having such a small detachment, Colonel Ivan Bohun, being one of the best strategists of the Zaporizhzhya Army , made the only correct decision - to block the "Black Way" in the direction of Uman.