ALTURA, Minn. – Railroad historian John Lueck, writing in the August issue of Trains magazine, calls the long-abandoned Winona and Southwestern railroad one of the difficult routes in the state. The climb 20 miles from Winona through Rollingstone to the Mississippi valley rim at Altura was 3.3% — and 4% in places The continuously twisting roadbed included 26 bridges, massive cuts through coulee walls, and two horseshoe curves. The route was poorly built, expensive to maintain, and dangerous. In 1892, seven crew members were killed. Among them were two engineers on a runaway train. Construction had begun in 1888 on an admittedly inferior route up Bear Creek. The earlier Chicago & St. Peter, which opened three decades earlier, in 1861, already had the preferred albeit also a stuff climb through Stockton to Lewiston. The Winona and Southwestern struggled for 46 years through but never competed successfully for grain from Iowa with other granger railroads. In 1934 the railroad abandoned the Altura rute and leased trackage rights to Lewiston on the older Winona and St. Peter route.

Low-cost stilt trestles. One of two high trestles on a horseshoe on the climb to Altura. Cost over-runs put construction at $12.5 million on today’s dollars – an astronomical $627,000 a mile. Trains need to be broken into sections at the trestles because the weight of a whole train would have been too much. It was 65 feet down.
Winona and Southwestern profile
The original rail route up the bluffs, the Winona & St. Peter, abused its monopoly. The Winona and Southwestern was organized to compete. Instead of going to St. Peter and the Minnesita Rver valley, the new railroad aimed 113 miles for Osage, Iowa. The original grandiose plan was to link Green Bay, Wisconsin, on the Great Lakes via Winona with with Omaha, Nebraska and the Union Pacific mainline to the West Coast. Money ran out, however, at Osage.
In Winona the railroad wound along the river south to Homer and then turned 180 degrees and headed along the bluffs to Minnesota City and then up Rollingstone Creek and the climb up Bear Creek to Altura.