The district was created in 1817 as Bilsteiner Kreis, in 1819 the capital was moved to Olpe. During the reorganization of the districts in 1969 several of the municipalities in the district were joined together to become cities, but the district itself was only changed a little bit. Even in the second reorganization 1974 it stayed nearly in the same borders as in 1817.
The left half of the coat of arms show the cologne cross, as the Olpe area belonged to the bishops of Cologne. The right side show the sign of the Lords of Fürstenberg, who were governors for the bishops in this area.