A native of Bangor, Maine, Day began playing piano at age five and guitar at age 12. By 15, he was writing his own songs and performing across New England. Shortly after graduating high school, Day became a fixture at college coffeehouses across the U.S. He wrote, financed and released his first effort, Australia, which was named Best Debut Album at the 2001 Boston Music Awards. The Boston Globe called Day “gorgeously seasoned, far beyond his years” with “a brave, beautiful singing voice.”