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- 1991 - Leland High Sierra Snowplay Inc. opened for business under its current ownership. The business was volume based for years, and operated with minimal staffing. There were no lifts; persons walked up the big hill by the hundreds, carrying black rubber inner-tubes and plastic sleds or saucers. The owner even lived on site, in his office.
- 1991 to 1993 - The High Sierra Music Festival was held in Leland Meadows for three summers. The festival soon outgrew Leland Meadows and was moved to Bear Valley and then Quincy, where it still held today. Leland Meadows was also the site of the first Strawberry Music Festival in 1982, now held alternately in Grass Valley and Tuolumne.
- 2005 - The "free for all" system under which the hill operated for more that a decade is discontinued, "lanes" are installed on the hill for the first time ever, and the first "Park Safety Staff" is created to manage the improved ill operations.
- 2006 - Park Safety Staff begins implementing new safety procedures which dramatically reduce accidents and injuries.
- 2008 - After years of bureaucratic paperwork and a quarter million dollar investment, Leland Snowplay officially starts operating its first surface lift on January 1. The surface lift is capable of transporting up to 8 persons per minute to the top of the Big Hill. Although walk-up service will continue to be offered for years, there is such a great demand for lift service that a second lift is put into operation 11 months later for the 2008-2009 season.
- 2012 - Nearly two decades since the High Sierra Music Festival moved out of Leland Meadows, the Lazy Summer Days Music Festival is held at Leland Snowplay.
- 2015 - In respond to the terrible drought to start the 2010's, Leland Snowplay invests nearly a million dollars into a state of the art snow-making system. If the temperatures are cold enough at night, our staff can produce tons of new snow nightly to add to what Mother Nature gives us.
- 2017 - Since the installation of our surface lifts in 2008, a common demand was for lift service for the Kiddie Hills. In response, another half-million-dollar investment was made into a Magic Carpet Lift System, an escalator-type lift that allows kids (and adults) to easily access the Kiddie Hill. Walk-Up ticket options are discontinued soon after, making Leland Snowplay entirely lift served.
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