Plans to build a railroad through the Fretter and Werden 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 several deep cuts in the terrain proved to be more difficult than expected and the opening of the line was delayed by almost a year. The Finnentrop-Wennemen line was inaugurated on 14.01.1911 and operations began on 16.01. Older railroad lines already existed from Lennestadt-Altenhundem to Schmallenberg through the upper Lennetal valley (inaugurated in 1887) and on to Bad Fredeburg (inaugurated in 1889). On 30.09.1911, the inauguration of the Bad Fredeburg-Wenholthausen line was celebrated as the last gap closure. All of these lines contributed significantly to the economic development of the Sauerland at the time, which in turn led to a considerable improvement in people's living conditions. Trains of supra-regional importance only ran here from 1963 to 1965 via an express train connection between Cologne and Paderborn, popularly known as the "Cardinal Express". In the course of general modernization, however, the railroad lines became uneconomical in the second half of the 20th century. Passenger services were discontinued on all the lines in 1966. Freight trains continued to run on some sections until the turn of the century.
In 1995, the municipality of Finnentrop was the first local authority to end the slumber of the old railroad line and began upgrading it from Lenhausen to Fehrenbracht into a cycle path. In 2004, the town of Schmallenberg and the municipality of Eslohe began upgrading the railroad line from Schmallenberg to Bremke as a cycle path, which was inaugurated on August 11, 2006. In the years 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 completed as a family-friendly circular route over 84 km through the four municipalities of Finnentrop, Eslohe, Schmallenberg and Lennestadt.
In spring 2009, the state of North Rhine-Westphalia began converting another old railroad line into a cycle path. From Eslohe- Sallinghausen to Wennemen, the cycle path along the Wenne created a link between the SauerlandRadring and the RuhrtalRadweg. In the 2012 season, the established SauerlandRadring was given a further building block with the 40 km long "HenneseeSchleife", the high-quality cycle path offer in the Sauerland was significantly improved. Since then, the HenneseeSchleife has led through the Wennetal valley and from Wennemen along the RuhrtalRadweg to the district town of Meschede. In the town center of Meschede, the cycle path turns south and leads along the Henne to the eastern shore of the Hennesee. The route then follows existing cycle paths along the B55 via Eslohe- Reiste to Bremke, where it reaches the existing SauerlandRadring.
Since 2012, there has been a connection between the "SauerlandRadring" and the "RuhrtalRadweg" via the HenneseeSchleife loop of the SauerlandRadring.
The "Ruhr-Sieg-Radweg" was opened on 25.06.2014 as part of the "Bergische Panoramaradwege" network. The long-distance cycle path runs for 115 km, mainly on old railroad lines of the former 239e route from Meschede via Eslohe, Finnentrop, Olpe,
Freudenberg to Kirchen/Betzdorf. From Meschede to Finnentrop, the cycle path runs along the SauerlandRadring.