Milwaukee Wisconsin outdoor train Northside 1950's Do you Remember this???? - Model Railroader Magazine

There was something similar south of Milwaukee, perhaps in Racine, which was closer to our house, and my recollection is that it was called Kiddieland, not Kiddietown, but just maybe owned by the same person or persons.  But yes they had a train ride, and if memory serves, a sort of boat ride in a circular elevated tank with the boats attached to a central hub.  I also recall very small and tired looking ponies.  My sister loved the ponies.  And I do believe that you could get discounts, maybe even free rides, if you had enough foil and paper disc bottle caps from bottles of milk from a delivering dairy.  On the south side that was Huebner's Dairy, and I well remember that in the days before homogenized milk on cold days in our milk chute the cream at the top of a bottle of milk would freeze and push the cap up beyond the top of the bottle.  

There was also something similar with rides, but mostly carnival type rides, that would make the rounds of the more marginal shopping center parking lots around Milwaukee but that was in the later 1960s and 70s.  They may have had a train as well but more cartoon like, like from Disney's Dumbo cartoon.

Dave Nelson