Cuyuna Rolling Hills was developed in two stages. The first nine holes were laid out in 1932, and with some small design changes, has kept that basic design up to this day. Harry Middlebrook, with help from both the mining and railroad companies, is primarily responsible for the original design. The second nine, designed by Donald “Dogleg” Herfort, was added in 1988. This composite course, carved out of the Northern Minnesota woods, requires an accurate driver, skill in handling the uneven uphill, downhill, and sidehill lies, and a first class game to master the challenging putting surfaces here at Cuyuna.