Pleasant Mountain, 4 miles west of Bridgton on Route 302, is the local ski mountain and the oldest major ski area in Maine. Its 1,300 feet of vertical drop across 44 trails and 245 skiable acres makes it a solid intermediate mountain — not Sugarloaf, but far less crowded and much more accessible from southern Maine and coastal New Hampshire. Snowmaking covers nearly all of the terrain, keeping conditions reliable when natural snow is thin.
The mountain is particularly good for night skiing: 19 trails are lit and run until 9pm most evenings, which makes it feasible for day-trippers who work in Portland to head up after work. In summer, the mountain opens for hiking; the summit at 2,006 feet gives wide views across the lakes region to Mount Washington on a clear day. Boyne Resorts, the current owner, added a high-speed detachable quad chair in 2024, replacing the old Summit Express triple.