Plans for a railroad through the Fretter and Wenne valleys date back to the 1860s, but construction did not begin until 1907. The construction work with the two tunnels near Finnentrop and Kückelheim and some deep cuts in the terrain turned out to be more difficult than expected and so the opening of the line was delayed by almost a year. The inauguration of the line Finnentrop-Wennemen took place from 14.01.1911, the operation started on 16.01. Older railroad lines already existed from Lennestadt-Altenhundem to Schmallenberg through the upper Lenne valley (inauguration 1887) and further to Bad Fredeburg (inauguration 1889). On September 30, 1911, the inauguration of the Bad Fredeburg-Wenholthausen line was celebrated as the last gap closure. At that time, all these lines contributed significantly to the economic development of the Sauerland, which in turn led to a considerable improvement in the living conditions of the people. Trains of supra-regional importance ran here only from 1963 to 1965 through an express train connection between Cologne and Paderborn, popularly known as the "Cardinals Express". In the course of general modernization, however, the railroad lines became uneconomical in the second half of the 20th century. Passenger service was discontinued on all the lines in 1966. Freight train traffic still existed on some of the lines until the turn of the century.
In 1995, the municipality of Finnentrop was the first municipality to end the slumber of the old railroad line and began the expansion from Lenhausen to Fehrenbracht into a bike path. In 2004, the town of Schmallenberg and the municipality of Eslohe began to upgrade the railroad line from Schmallenberg to Bremke as a cycle path; the inauguration took place on August 11, 2006. From 2005 to 2007, the last section from Eslohe to Fehrenbracht was upgraded as a cycle path through the so-called "Fledermaustunnel". With the inauguration on May 26, 2007, the "SauerlandRadring" was complete as a family-friendly circular route over 84 km through the four communities of Finnentrop, Eslohe, Schmallenberg and Lennestadt.
In spring 2009, the state of North Rhine-Westphalia began upgrading another old railroad track into a bike path. From Eslohe- Sallinghausen to Wennemen, the cycle path along the Wenne created the connection between the SauerlandRadring and the RuhrtalRadweg. In the 2012 season, the established SauerlandRadring received a further building block with the 40 km long "HenneseeSchleife", and the high-quality range of cycle paths in the Sauerland was significantly improved. Since then, the HenneseeSchleife leads through the Wennetal and from Wennemen on the RuhrtalRadweg to the district town of Meschede. In the city center of Meschede, the cycle path turns south and leads along the Hennen to the eastern shore of the Hennesee. On existing cycle paths along the B55 it then goes via Eslohe- Reiste to Bremke, where the existing SauerlandRadring is reached.
Since 2012, there has been a connection between the "SauerlandRadring" and the "Ruhrtalradweg" via the HenneseeSchleife of the SauerlandRadring.
In the network of the "Bergische Panoramaradwege" the "Ruhr- Sieg-Radweg" was opened on 25.06.2014. The long-distance cycle path leads over 115 km mainly on old railroad tracks of the former railroad line 239e from Meschede via Eslohe, Finnentrop, Olpe,
Freudenberg to Kirchen/Betzdorf. From Meschede to Finnentrop, the cycle path runs along the SauerlandRadring.