Between 1350 and 1360 Ortolf von Trier, a knight of the Teutonic Order and the Komtur of Elbląg, founded a fort in Galindia, probably near an Old Prussian settlement. The first mentioning of the fort was a document from 24 September 1360, after Ortolf invited Masoviancolonists, among whom the settlement became known as Szczytno. The first custodian of the settlement was Heinrich Murer. In 1370 the wooden fort was destroyed byLithuanians led by Kęstutis, after which it was rebuilt using stone. The name Ortulfsburg gradually changed into Ortelsburg. The settlement grew in size owing to its location on a trade route from Warsaw to Königsberg (now Kaliningrad).
The castle was occupied by Polish troops during the Thirteen Years' War. With its inclusion in the Duchy of Prussia in 1525, it lost its importance as a border fortress and began to decline. Margrave and regent George Frederick (1577–1603), who enjoyed hunting nearby, began the redevelopment of the area. Among his projects was the rebuilding of the castle into a hunting lodge.
Ortelsburg became the seat of Landkreis Ortelsburg, one of the largest in East Prussia, in 1818 after Prussian administrative reforms, with Ritter von Berg chosen as the first district administrator. It was almost completely destroyed on 30 August 1914 at the beginning of World War I by troops of the Russian Empire, with 160 houses and 321 commercial buildings burning down.
References:Kakesbeck is one of the largest medieval fortifications in Münsterland and the oldest castle in Lüdinghausen. The imposingly grown complex originated in 1120 as a motte, a small hilltop tower castle. After numerous changes of ownership, the castle was extended onto two islands, but it was not until the 14th century that it underwent significant alterations and extensions under the von Oer family. The estate experienced its heyday in the middle of the 18th century, when it covered an area of almost one square kilometre and consisted of five further outer castles in addition to the core castle, which were secured by ramparts and moats.
The well-maintained condition of the castle today is thanks to the late Wilfried Grewing, the former lord of the castle. The foundation named after him has been particularly committed to preserving the property since 2020.