From the bar at Wilmot Mountain. The caption says 1938, and there appear to be two tow ropes in the picture. Here's what wikipedia has to say about the place:
Located in the southern region of Wisconsin's Kettle Moraine, Wilmot Mountain is the result of Glaciation. The self-proclaimed “Matterhorn of the Midwest” was founded by Walter Stopa in 1938 after a thorough research of the area’s topography. With a vertical drop of 230’ it is a relatively small hill. It is also one of the few hills where the mountain is wide open, with few trees or barriers to crossing the hill. A skier can transverse several runs while skiing downhill. Night skiing is available on the entire hill.
Wilmot Mountain is located 60 miles (97 km) North of Chicago and has been owned by the same family since it was founded. It still retains a non-corporate look and feel, from the vintage lifts to the huge open fireplace. Most days small aircraft from the nearby Westosha airport can be seen high above, circling the hill.