I am no authority on amusement parks and rides but I do know a bit about Muskego Beach park.
My grandfather ran the park from 1928 to 1944. My mom and her siblings grew up on the grounds and worked there all summer. My mom too was born in 1922 and she died last September. She would often ride the Cyclone every day, all summer. I had to piece together a lot of information and do much research as my mom's memory was bad.
There were two roller coasters at the park. First the Cyclone (1928/1929 - 1949) and then the TailSpin (1949/1950 - 1983, idle since 1977). Ironically, the Cyclone was damaged considerably by what was equivalent to a cyclone and replaced. Both were of timber and I need not tell the experts how important that is.
The Cyclone was very long, 4,000 feet, while the TailSpin was 2,200 feet in length (but had a larger width and more variation). The Cyclone had a single loop at each end, entrance at the middle of the a very elongated oval shape, with the ends at a mid-elevation, drops to grade after the end loops then varying but tall climbs (and back down) with the center points at grade.
The picture is the only detailed shot from grade I have seen without interference (I would certainly appreciate a digital copy, if possible) and therefore precious as an historical document. This would be the end loop, just a portion of the long and narrow ride.
If this is not the Muskego Beach Cyclone, it would be a twin. So, I am pretty sure the family took the car or train to the site. At the time, it might have been a 3-4 hour trip, one way. Cars started arriving in droves as of the late '20s but the train was still popular, dropping people off at the station about a mile or so to the south of the beach and park. There was a hotel at the site, but this was usually a day trip kind of place (often from the Milwaukee area) except that many cottages on the lake would rent for the summer, or for weeks at a time.
So, there you go.
Jeff Oertel