Winter Park originally began as two separate settlements – Old Town and Hideaway Park – in the late 1920s/early 1930s. The town grew rapidly with the establishment of 26 tourist cabins, a café, a service station (called "Doc's Place"), a water tunnel, and several additional businesses. In 1978, the town name was officially changed to "Winter Park" and incorporated.
Winter Park Ski Resort opened in 1939. In 1975, the resort added its first additional interconnected mountain peak called Mary Jane, and a second called Vasquez Ridge in 1986. In an attempt to make Winter Park a year-round resort, lifts are operated during the summer months for mountain biking.
Winter Park maintains a variety of attractions including: