The route of the Sheboygan Interurban Trail is based on the Interurban railway that connected the City of Milwaukee to Sheboygan.
In 1922, the right-of-way was acquired by The Milwaukee Electric Railway and Light Company for development of an improved rapid transit service from Milwaukee to Sheboygan. The Northern Route, the interurban electric railway from Milwaukee to Sheboygan since 1908, had stops in the mostly rural communities of Brown Deer, Thiensville, Cedarburg, Grafton, Port Washington, Belgium, Cedar Grove, Oostburg and Sheboygan.
This rapid transit was an electric railway system linking Milwaukee and many of the surrounding communities from its inception in 1905 to the end of all operations in 1951. During its operation, the Northern Route of the interurban line was also made famous for transporting African-American blues musicians to the main recording studio for Paramount Records recording label in Port Washington and ultimately in Grafton, Wisconsin. The idea of African-American artists from the rural South traveling to Grafton, Wisconsin in the late 1920s and early 1930s by taking the "electric train" seems fantastic.
Today, the Sheboygan Interurban Trail is a 14-mile paved and on-road trail that spans from the Ozaukee County/Sheboygan County Line to the City of Sheboygan. About 5.5 miles from the County line to the Village of Oostburg is off-road. The on-road sections traverse town roads with very, very low traffic volumes. About 1.5 miles of the on-road section traverses the main park road in the Kohler-Andrae State Park.