Bridgton is genuinely four-season, and each season has its advocates. Summer (late June through August) is the busiest, when Long Lake fills with boats and the lakeside camps and cottages come alive. The weather is warm and humid, and the drive-in theater runs nightly.
Fall foliage peaks in early to mid-October and is spectacular in the lakes region. The hills around Pleasant Mountain turn orange and red, and the lake reflections double the effect. Crowds are thinner than summer but the leaf-peeping draws visitors from as far as Boston.
Winter is when skiers arrive. Pleasant Mountain runs from December through March, with reliable snowmaking covering nearly all of its 44 trails. Night skiing on 19 lit trails makes weekday evenings viable even for day-trippers from Portland.
Spring (April through May) is mud season and generally the least appealing time to visit, though the lakes have their own quiet charm before the summer rush.
The Four on the Fourth road race on July 4th is a long-running tradition that draws runners from across New England and turns Main Street into a festive scene.