TC&W Oak Street Bridge

In 1872, the Hastings and Dakota Railway completed 72 miles of new railroad between Hastings, Minnesota and Glencoe, Minnesota. Later that year, the H&D would convey this line to the Milwaukee and St. Paul Railway, which would change its name to the Chicago, Milwaukee and St. Paul Railway Company (CM&StP) in 1874. Known as the Milwaukee Road, the railroad was beginning to amass a large collection of railroads throughout Wisconsin, Minnesota and Iowa. In 1880, an additional 128 miles were completed between Glencoe and Ortonville, Minnesota. The line would be conveyed to the Milwaukee Road that year. Also in 1880, the Milwaukee Road built an additional 69 miles from Ortonville to Bristol, South Dakota. Further extensions to the line would be made in 1881, when 10 additional miles were constructed to Andover. In 1882, a 30 mile segment of line, known as the "Benton Cutoff" was constructed between Cologne, Minnesota and Minneapolis, Minnesota. 29 additional miles were completed to Aberdeen the same year. In 1883, 26 additional miles would be constructed from Aberdeen to Ipswich, followed by 30 additional miles from Ipswich to Bowdle in 1885, and 32 miles from Bowdle to Glenham in 1900. Glenham was located on the Missouri River in north central South Dakota.

The Benton Cutoff allowed for quicker travel between Minneapolis and South Dakota. As a result, the Hastings to Cologne segment of this route lost importance to the Milwaukee Road. As the line was extended west, this route gained importance to the Milwaukee Road, and provided a possible connection to the Pacific Coast at Seattle. A subsidiary was charted to build a route between the Missouri River at Glenham and Seattle in Washington. Work began in 1906, and was completed in 1909. The Milwaukee Road then set out to double track and realign most of the line between Minneapolis and Aberdeen, and work was completed between 1912 and 1915. The only segment not double tracked was the Bird Island to Granite Falls segment. Traffic never justified the double track, and portions were removed beginning in 1934, with the Hopkins to Hector and Summit to Groton. The second track was removed between Granite Falls and Milbank in 1947, and the remainder removed in 1955.

In 1925, the Milwaukee Road declared bankruptcy, and reorganized as the Chicago, Milwaukee, St. Paul and Pacific Railroad in 1928. Financial issues continued for the Milwaukee Road, and the railroad again filed for bankruptcy in 1977. In an effort to reduce branch lines, the Appleton to Ortonville segment was sold to Burlington Northern Railroad in 1982, and the Ortonville to Terry, Montana segment to the State of South Dakota the same year. BN began operations on that line. By 1985, a suitor for the Milwaukee Road was being sought, and the Soo Line Railroad, controlled by Canadian Pacific Railway (CP) purchased the Milwaukee Road in 1986. The Hopkins to Appleton segment was sold to the Twin Cities & Western Railroad (TC&W) in 1991, and the Ortonville to Terry segment was sold to BN the same year. The Cedar Lake Junction to Minneapolis segment was abandoned in 1996, and converted to the Midtown Greenway. In 1996, BN merged with the Atchison, Topeka & Santa Fe Railway to form BNSF Railway. In 2023, CP merged with Kansas City Southern Railway to form CPKC. BNSF continues to operate the Appleton to Aberdeen portion of this line as the Appleton Subdivision, the Aberdeen to Hettinger, North Dakota segment as the Mobridge Subdivision, and the Hettinger to Terry segment as the Hettinger Subdivision. The TC&W continues to operate the Hopkins to Appleton segment, and CPKC operates the Bass Lake Spur between Cedar Lake Junction and Hopkins.