Shawnee Peak's skiing history dates back to 1935, when multiple groups started developing a winter recreation area on the northern slopes of Pleasant Mountain. The Bridgton Lions Club, Bridgton Chamber of Commerce, Bridgton Academy, Portland Ski Club, and Bridgton Civilian Conservation Corps joined together to construct the Wayshego Trail. The 1.5 mile trail was only the start of what was to come. This was Pleasant Mountain in the 1960's. Maine's first T-Bar was installed at Pleasant for 1953-54. At about 2,000 in length, the lift served the lower slopes of the ski area.
Around this time, Ray Erickson joined Russ Haggett as owner of the ski area. For 1955-56, Maine's second chairlift was installed at Pleasant Mountain. Later known as "Old Blue," the 4,300 foot double chairlift climbed to the top of the north peak of the mountain.

It was called Pleasant Mountain until just after the 1987-88 season when the owners found themselves in financial trouble. That summer, they sold the ski area to Shawnee Mountain Corp. for $1.4 million. Pleasant Mountain was subsequently renamed to "Shawnee Peak," the name of the owners' Pennsylvania ski area. The mountain changed owners once again in 1994 when it was purchased by Tom's of Maine executive Chet Homer in September.

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