The original train takes its name from the epic poem The Song of Hiawatha by Henry Wadsworth Longfellow.

[1] The first Hiawatha ran between Chicago and the Twin Cities on May 29, 1935, on a daily 6½ hour schedule over the 410 miles (660 km) to St.

[2] The four new class A locomotives had streamlining by Otto Kuhler, were oil-fired to reduce servicing time en route, and were some of the fastest steam engines ever built, capable of powering their five-car trains at sustained speeds more than 100 mph (160 km/h).

The Twin Cities Hiawatha was partially equipped in May 1942 with coaches, two diners, and two 'Tip Top Tap' cars which ran with the 1939 Beaver Tails and parlors.

These four cars had a drawing room and swiveling parlor seats, and at the rear there was a lounge area with an expanse of windows.

(One of these cars, #186 Cedar Rapids has been restored and is owned by a Minneapolis-based organization that operates the Milwaukee Road 261 steam locomotive.)

On July 18, 1960, the eastbound Afternoon Hiawatha struck a truck in the crossing in Newport, Minnesota, and derailed.

[8][9] Dozens of passengers on the train to Chicago suffered minor injuries, but only ten were hospitalized overnight.

From November 1971 to April 1985, a series of other trains also served the routing, providing a second daily round trip at most times.

Amtrak briefly reused the Twin Cities Hiawatha name for a Chicago-Minneapolis service from January 16 to June 12, 1972, and October 30, 1977, to April 30, 1978.

[12] The Twin Cities Hiawatha ran on the railroad's main line from Chicago and Milwaukee to St. Paul and Minneapolis.

[13] The current route, consisting of five subdivisions, is now owned by the Soo Line Railroad, an in-name-only division of the Canadian Pacific Railway.