Founded in 1919, Windermere retains much of the look and feel of the original George Cumming design. Cumming, who was head pro at Toronto Golf Club at the time, designed the course to build momentum through the first three holes, before it jolts golfers awake at the fourth, a 414-yard dogleg par four featuring a seriously tiered green. Water hazards, postage stamp–size greens and snug, tree-lined fairways challenge even low handicappers the rest of the way. One of Muskoka’s signature holes is the 179-yard, par three 11th. From a wildly elevated tee, golfers hit to a small, severely sloped green flanked by an enormous wall of striated pink and grey granite. Holes 12, 14 and 16 have undergone improvements, as have the amenities—a $1.5 million clubhouse opened in 2003.