First human settlements on the territory of the Chechersk region appeared about 100,000 years ago in the Palaeolith. There is one of the most ancient sites of primitive men of the modern physical type (Cro-Magnon men) on the territory of the region – so-called Berdyzhskaya settlement located 300 meters away from the village of Podluzhye.

Chechersk was first mentioned in the Ipatiev Chronicle in 1159 as a town of the tribe of Radimichi. Till the middle of the 14th century Chechersk was part of the Chernigov Principality. Later it was the center of the volost (district) in the Vilno wojewodztwo (province). In 1510 the town was granted the Magdeburg right. After the reforms of 1566 Chechersk was included into the Rechitsa powiat of the Minsk wojewodztwo. The Chechersk starostwo was always in state possession and since the 16th century was passed into life ownership of different statesmen for a quarter (the treasury received 25 per cent of nthe incomes). Since 1772 (after the first partition of the Rzecz Pospolita) Chechersk was ruled by the Russian Empire; till 1919 it was part of the Rogachev uyezd (district) of the Mogilev province.

The Chechersk starostwo was withdrawn from Hetman of the Great Principality of Lithuania Mikhail Kazimir Ahinski and in 1774 was given to the first Belarusian Governor-General Z.G. Chernyshev. The town was rebuilt in a classical style; a stone town council, three Orthodox and one Roman-Catholic churches were built. There was a serf theater in the town and a glass plant producing Bohemian, sheet and window glass.