Bobolice was mentioned for the first time in documents quite late, on 12th of August 1320. The name Bobolice appeared in a document of purchase written in Słupsk. The document stated that borders of the Order reached the Bobolice Land. The name of the town was mentioned again in a document issued on April 17th, 1340 by bishop Fryderyk von Eickstadt, when Bobolice was granted town rights under Lübeck Law. At that time Bobolice was also given a coat of arms. Two knights: Bartuszewicz and Goldebeck were responsible for implementing the settling rights. Trade started to develop rapidly in Bobolice, which attracted many new settlers, especially from Germany. The town, however, did not manage to develop due to pests, fires and frequent changes of proprietors. It was owned, among others, by the bishops of Kamień Pomorski and Pomeranian families.

A new chance for development showed up in 1626 when Bobolice was granted a privilege to organise four fairs a year. On 15th of September 1653, Katarzyna Kleyers was accused of witchcraft, signing a pact with the Devil and killing children. She was burned at the stake in Bobolice. In the 17th century the town became part of Brandenburg and started to decline, whereas the 18th century brought its renaissance, when a railway connection with Połczyn Zdrój and Sławno was opened, and the road to Koszalin was built.

Before the outbreak of World War II the town numbered 6,147 inhabitants, it had its own powerhouse, sawmill, brickyard, furniture and agricultural machinery factories. Bobolice was taken by the Red Army on March 5th, 1945. The town, which had been destroyed in 75%, was annexed to Poland. Renovation works began in the 1960’s, trade and craft began to develop, culture and education gained on importance.