Since 1167 silver ore was mined close to Iseringhausen, near Drolshagen, through authorisation from Emperor Friedrich I. Barbarossa. Since the end of the Middle Ages, various ore mines were established in the southern part of Drolshagen. The metals mined were processed in ironworks and hammer mills. In 1477 Drolshagen was granted town charter by the Elector of Cologne, Ruprecht. Town wall construction had already began two years earlier. Drolshagen joined the Hanseatic League at the beginning of the 17th century. At that time steel processing and the tanning trade were of importance, which lasted until the 20th century. Since 1658 a weekly market and three fairs a year have been held here.

In the course of the Napoleonic wars our region was assigned to the Grand Duchy of Hesse-Darmstadt in 1802. After the Congress of Vienna, Drolshagen came under Prussian administration with the Duchy of Westphalia in 1816. In the year 1838 the medieval buildings within the city walls completely burned down apart from the church. The reconstruction, carried out within two years, with the straight main street and the side streets branching off at right angles, still characterises the cityscape today. Drolshagen was spared major destruction during World War II.

Although the town was still characterised by agriculture until the 20th century, industrialisation had already started in the second half of the 19th century and increased from 1903, when Drolshagen was connected to the railway network. Since 1969 Drolshagen has been twinned with the Dutch municipality Joure, today part of De Fryske Marren.

Of the surrounding villages that belong to Drolshagen it is especially recommended to visit: The beautifully situated water mill in Eichener Mühle, already documented in the middle of the 13th century. The chapel St. Michael in Sendschotten with a statue of Our Lady, which is carried in a procession, the "Ümmegang", through fields and meadows at the beginning of July. The old chapel "Maria Geburt" in Hützemert and the baroque pilgrimage chapel "Rosenkranzkönigin" in Wenkhausen. However, all churches and chapels are worth visiting and there are many beautiful places to visit in the region’s natural environment.

The Drolshagen coat of arms is divided into four sections by the Cologne cross. The three blue diamonds in fields one and four were the coats of arms belonging to the lords of Drolshagen. The anchor in fields two and three is the symbol of St. Clement, the patron saint of the parish church. The arrow within the anchor is in remembrance of St. Sebastian, to whom an altar was dedicated by the Schützengilde when the town was founded.