Prinsenstraat is a street in Bredevoort’s old centre. It begins as a side street off Landstraat and runs northwards to ‘t Zand.
According to tradition, the street takes its name from Maurice of Orange, who advanced with his army along this route towards Bredevoort Castle during the Siege of Bredevoort in 1597. This street once ran parallel to the town wall. The houses were built against or on the foundations of that wall. From the bend near Kerkstraat to the end of Prinsenstraat, at the building now known as Sint Bernardus, seven defensive towers stood in a row. The Aalterpoort stood between the second and third towers.
After the town wall was demolished in the 17th century, an earthen rampart was constructed on the western side, with Bastion Vreesniet behind Prinsenstraat. Its terreplein still survives and is now also known as the “stadsweide”. Once the town wall had been removed, an open connection was created with the castle grounds. After the castle moats were filled in, ‘t Zand developed there; well into the 20th century, it really was sandy ground.
In the 20th century, Prinsenstraat was a thriving shopping street. Most of its shops did not survive into the modern era. Several houses have been designated as municipally listed monuments.