The University of Wisconsin posted the above photo on Facebook from circa 1911 of an epic toboggan run from Observatory Hill to Lake Mendota. According to an accompanying blog post, the run was 1200 feet long including wooden and ice segments. By 1930 it got even more sophisticated with lights and concrete.
The last time I was on an actual toboggan was at Camp Upham Woods for winter retreat with the Madison Boy Choir maybe circa 1985 . The camp (operated by the State of Wisconsin) had a six-person wooden toboggan and “enough snow” was never a problem. Looking at the UW picture, its good that they had a narrow track to guard against wipeouts. The Upham Woods run was an approximately 200-foot wooden track without sides which left lots of opportunity for jack-knifing into a glorious clouds of powder.