This season, Shawnee Peak, originally known as Pleasant Mountain, will celebrate 70 years of skiing and riding. Truly a pioneer resort of the sport, Shawnee Peak is the oldest continually-running ski and snowboard area in Maine.

A 1908 postcard from the Route 302 causeway before Pleasant Mountain had trails.

The 30's

In the earliest days, the slopes of Pleasant Mountain consisted largely of cow pastures. Having sought permission from the cow farmers, skiers simply waited for the bovine to retire to barns for the winter, took down the fences and skied to their hearts content. Skiers from Portland and the local area soon came together to direct the mountain's development in its early years.

• 1936 – under the direction of Academy Headmaster, Harry Sampson, Bridgton residents and students at nearby Bridgton Academy cut the first ski trails.
• 1937 the Civilian Conservation Corps cut the top to bottom "Wayshego Trail", which is now known as "Jack Spratt".
• Sunday, January 23, 1938 – Official opening day. Amenities included a 16' x 32' shelter and 1,100' rope tow. More than 500 winter enthusiasts showed up on this historic day for a day of skiing, tobogganing, ski jumping and ice skating.