Kriva Palanka or Egri Dere is founded in 1634 by Bajram Paša, the vizier of the sultan Murat 1st.
As early as in 1661, Evlija Chelebija described Kriva Palanka as a town of approximately 800 households. Later, in 1689, the people from the north - eastern Macedonia organized an rebelion against the Turks. The Karpoš rebels liberated the town, which only lasted for several month, until the leader was killed in Skopje.
Kriva Palanka is also related to the life, work and death of Joachim Krčovski, a priest and religious master, Macedonian educator and founder of the new Macedonian literature in the 19th century. In 1817 he founded a church school in the house of Enger, near the church of St. Dimitrija (built in 1833). Later, the new Kelijno School was formed in the yard of the church. The school was working until 1927. According to a legend, the great Macedonian educator Kiril Pejchinovikj was buried in the old graveyard in the yard of the church.
According to the census of the 19th century it was listed as a town with Christian and Turkish population. In 1870, Kr. Palanka had 4352 inhabitants (3252 Macedonians and 1100 Turks). It had a bazaar with 250 stores and rich merchants. Among them was Hadzi Stefan Beglikčija, remembered as the man who got permission from the Sultan to build the monastery of Saint Joachim Osogovski. It is assumed that the memorial in front of the temple speaks of the conformation, which also guaranteed its protection.
The people of the region took an active part in the Ilinden Uprising in 1903. Macedonia and Kriva Palanka were liberated from the Turkish rule in 1912.
From 1912 -1915, the region was governed by Serbs and from 1915 till 1918 by the Bulgarians. In 1918, Macedonia and Kriva Palanka became a part of the Kingdom of Serbs, Croats and Slovenians, regardless of the will of the Macedonian people. Between the two World Wars, Kriva Palanka experienced a decline instead of progress.
During Second World War the Kriva Palanka was governed by the Bulgarian Axis forces, a period that lead to 139 partisans and 128 civilians dead. After the liberation (October 8th 1944), and the creation of a Macedonian state within Yugoslavia, a new phase of the development began.