The first Jews began to settle in Kholui at the end of the 18th century. By the end of the 19th century Jews constituted a majority of the town's population. Most Jews were involved in the lumber industry or were peddlers.
During the Russian civil war the Jews of Kholui suffered greatly, including by impoverishment. After the establishment of Soviet rule, the name of the town was changed to Lipen. After the confiscation of land owned by big landlords, many Jewish families of Lipen began to engage in agriculture. In 1926 a Jewish agricultural cooperative named "National" was established near the town. In the first years of Soviet rule there was an increase in Zionist activity in Lipen, including that of the Zionist youth organization Kadima. Subsequently, Zionist groups were forced to operate underground. In 1926 there were 441 Jews in Lipen, comprising 58% of the total population.
Lipen was occupied by the Germans on June 30, 1941. Almost immediately all the Jews were forced into a ghetto encompassing a couple of houses in the area close to the bank of the Svisloch River and were ordered to wear the Star of David on their clothes. Several young Jews were taken to the bridge over the Svisloch, pushed into the river, and shot.
Most of Lipen's Jews were murdered in a single operation carried out either in July-August or October 1941, when they were forced into a house and burned alive. About 200 Jews were killed in this massacre. The perpetrators were, evidently, members of Einsatzgruppe B, the Security Police, and the SD, assisted by local policemen. Some Lipen Jews succeeded in escaping to the forest.
Lipen was liberated by the Red Army on June 28, 1944.