The video notes that two colleges in Winona have extensive enrollment from the Cities, and one person is quoted as liking the idea of six trains to Chicago.
It was not that long ago that Winona had six trains to Chicago, on two competing railroads, on timings that were sometimes competitive and sometimes complementary.
The Milwaukee Road was still running almost the same service it offered during World War II. The westbound schedule in effect at April 28, 1968 included One, The Pioneer Limited, off Chicago 10.30, Winona 4.55, arriving St. Paul 7.00. If that was too early, 55, making local stops across Wisconsin and along the Mississippi, off Chicago 11.30, offered a breakfast-time departure from Winona at 8.00, arriving St. Paul 10.40. Five, The Morning Hiawatha, off Chicago 10.30, reaching Winona at 4.21 (convenient for suitcase collegians) and into St. Paul at 6.25. Three, The Afternoon Hiawatha, left Chicago at 12.35, and on a faster schedule reached Winona at 5.26 and St. Paul at 7.15.
Going east, Six, The Morning Hiawatha, left St. Paul at 7.30, reaching Winona at 9.39 and Chicago at 2.45. A local service, 58, left St. Paul at 10.10, reaching Winona at 12.35 and LaCrosse at 1.45. This train was timed to connect with The Afternoon Hiawatha at New Lisbon. Anyone riding it end-to-end was doing so for the adventure. Two, The Afternoon Hiawatha, left St. Paul at 12.40, reaching Winona at 2.20 and Chicago at 7.25. There were no good early evening. 56, The Fast Mail, left St. Paul at 8.15 and Winona at 10.10, possibly a good option for collegians returning from home, then continuing to Chicago at 5.00. Four, The Pioneer Limited, left St. Paul at 11.20, calling at Winona at 1.12 and reaching Chicago at 7.45.
The Milwaukee Road was seeking permission to discontinue One and Four, 55 and 58, and would soon seek permission to discontinue Two and Three. Perhaps the petitions are still public record someplace, and they might include passenger counts for Winona.
The Burlington had already begun retrenching. Westbound, 21, The Morning Zephyr, often three or four cars, left Chicago at 8.15, reaching Winona Junction across the river in Wisconsin at 12.55 and St. Paul at 3.15, convenient for skipping Friday afternoon classes. The Afternoon Zephyr, 23, was combined with the Empire Builder and the North Coast Limited, leaving Chicago at 1.15, reaching Winona Junction at 6.08 and St. Paul at 8.00 with through service to Fargo and the Pacific Northwest. Fridays and Saturdays 21 was a separate train leaving Chicago at 4.55, calling at Winona Junction at 9.55 and reaching St. Paul at 11.25. That schedule might have been dictated by school schedules elsewhere on the line. An overnight service on 47, The Black Hawk, combined with The Mainstreeter and the Western Star, left Chicago at 10.30 with a 5.10 stop at Winona Junction and a 7.20 arrival at St. Paul. Coach passengers would change at St. Paul for Dakota and Pacific Northwest destinations.
Eastbound, The Morning Zephyr ran with the Empire Builder and North Coast Limited as 22, leaving St. Paul at 8.10, Winona Junction at 9.42 (and racing The Morning Hiawatha to LaCrosse) and reaching Chicago at 2.55. The Afternoon Zephyr picked up transfers off The Mainstreeter, offering a 4.25 departure from St. Paul, reaching Winona Junction at 5.47 and Chicago at 11.10, providing the early evening option missing from The Milwaukee Road's schedules. The Black Hawk took Western Star transfers out of St. Paul at 10.45 with a 12.32 stop at Winona Junction and a 7.00 arrival in Chicago.
Most of that service remained until Amtrak Day. It's possible that the rationalization of service under Amtrak auspices destroyed much of the connectivity possible in the upper Midwest, such as Crookston to Winona or St. Cloud to LaCrosse. On the other hand, the people of Winona might have withdrawn their business from the trains. In the abstract, high-speed trains have appeal. In practice, the farebox test might have a strict grading curve.