Skip Bailey

Award-winning songwriter Skip Bailey is a country and folk singer-songwriter from Maine whose songs reflect the grit, humor, and heart of rural life. He describes his work as “salt of the earth songs for salt of the earth folks,” a phrase that reflects his commitment to honest storytelling and connection to place. His music blends country, folk, and maritime influences into lyrical portraits of everyday people: fishermen, farmers, dreamers, and working folks who keep Maine’s traditions alive.

Performing across the state from Kittery to Lubec, Skip has earned a loyal following for his down-to-earth performances and his unique and powerful vocals. He currently holds a residency at Allagash Brewing Company and has played notable venues including Blue, The Apohadion Theater, Absolem, and Fogtown Brewing Company. His upcoming single, which won the 2025 Maine Songwriters Association’s 15th Annual Songwriting Contest, showcases his authentic voice and lyrical storytelling. Skip has also been featured on WERU’s Country and Northeastern radio show, joining the ranks of Maine’s next generation of songwriters carrying forward the region’s rich folk tradition.