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Sugarloaf, Maine

With a prime location at the base of the mountain, the Widowmaker, with its sun-drenched deck, is a go-to après spot for Sugarloafers. Live musicians and DJs perform every Friday and Saturday, and when the warm spring weather rolls around, the music moves outside to “The Beach,” where spring skiing fanatics have flocked to the legendary Reggae Fest for nearly 30 years.