The town’s location was favoured by the good climate in the Attendorn-Elsper Limestone Double Basin (Attendorn-Elsper-Kalkdoppelmulde), the fruitful soil and favourable transport potential, and was already attracting people in prehistoric times. Heavier settlement, however, can be traced only as far back as the Middle Ages.
The town lies at the crossroads of two former long-distance roads, the Heidenstraße (“Heath Road”) and the so-called Königsstraße (“King’s Road”). Here, in Charlemagne’s time, arose a parish. Under the St.-Johannes-Kirche (church) are found the foundations of an old missionary church. In 1072, Archbishop Anno of Cologne endowed the Grafschaft Monastery and granted it, among other things, rights to an estate in Attendorn. Indeed, the monastery’s endowment document stands as the town’s earliest documentary mention.
In 1222, town rights, on the Soest model, were granted the town under Engelbert II of Berg. Schnellenberg Castle, built about 1200, and the acquisition of the Waldenburg (another castle) in 1248 served to safeguard Cologne’s interests in the region.
Attendorn’s heyday was brought about not only by its nine guilds but also, and mainly, by its wool and linen weavers. Furthermore, the town’s political and ecclesiastical status as a bulwark against the County of Mark and as seat of a deanery in the old Archbishopric of Cologne brought it wealth and prosperity. As the Sauerland’s only town, Attendorn joined the Rhenish League of Towns in 1255. Attendorn was only an indirect member of the Hanse, and was thus represented at the Hanseatic League’s great assemblies by the town of Soest.
By about 1200, Attendorn was already home to one of the archbishopric’s mints. Mediaeval coins from Attendorn have been found as far afield as Brussels, Lubnice (Poland) and the island of Gotland.
From the early 14th century until today there has existed a hospital with a church and graveyard outside the town’s walls. In 1420, Heinrich Weke endowed the Ewig Monastery. In 1429, he also added a hospital for the poor. For a time, the town was so well off that it could even grant the Archbishop of Cologne himself credit. Moreover, the town also supported him during his dispute with the town of Soest. In 1444 and 1445, the town helped the Archbishop conquer the castle and the land of Bilstein in the so-called Soest Feud.
Four times, in 1464, 1597, 1598 and 1613, the Plague beset the town. Great fires, too, ravaged the town in 1613, 1623, 1656, 1710, 1732, 1742 and 1783. The one in 1656 destroyed half the town. Attendorn also suffered as a result of war, sackings and occupations. Examples include the War of the Limburg-Hohenlimburg Succession in 1280, the Soest Feud from 1444 to 1449, the Truchsess War in 1583 and 1584 and the Thirty Years' War from 1618 to 1648. Attendorn reached its deepest economic despair in Napoleonic times, only recovering from the downturn in the mid 19th century.
The rise of Nazis and the Second World War affected Attendorn much like the rest of Germany. An Attendorn teacher and historian, supported by the government, documented the persecution of Attendorn Jewish families under Nazi rule. As in many places, this included destruction of property, boycotting Jewish stores, approriating factories, and shipping Jews to concentration camps. Attendorn lost many citizens during the war and suffered heavy destruction under bombing on 28 March 1945, and also on 15 June that same year as a result of a munitions explosion.
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