The line was originally built between Hopkins and Cologne, Minnesota, in 1876 by Hastings and Dakota Railroad.

In 2012, the TCWR purchased the Sisseton Milbank Railroad and it now operates as a subsidiary of the Twin Cities and Western Railway.

Until Hiawatha Avenue (Minnesota State Highway 55) was reconstructed in the 1990s and plans for the Hiawatha Line light rail service entered late stages, the Twin Cities and Western operated on Canadian Pacific's Bass Lake Subdivision through the 29th Street railway trench in Minneapolis, now known as the Midtown Greenway.

The tracks continued along the former Milwaukee Road Short Line into Saint Paul, where TC&W would access rail yards operated by Canadian Pacific, the Minnesota Commercial Railway, and others.

[7] In order to protect a potentially important shipping route, TC&W purchased the Dan Patch Line Bridge over the Minnesota River in Savage.

TC&W has trackage rights over CP's MN&S Subdivision to reach Savage, and as of the fall of 2022, was seeking state funding to rehabilitate a section of track in Savage that would allow direct service to Port Cargill and neighboring grain elevators to resume.