was born in New York City. His mother, Mary (née Peckham), was a piano teacher at The Pennfield School in Portsmouth, Rhode Island. His father, Dr. Thomas Charles Day, is a retired professor of music history at Salve Regina University in Newport, Rhode Island. His mother has English, Irish, and Welsh ancestry, while his father is of Irish and Italian descent. Day spent most of his childhood in Middletown, Rhode Island. Day attended Pennfield School and graduated from the Portsmouth Abbey School, both in Portsmouth, Rhode Island. He starred on the baseball team at the Portsmouth Abbey School, playing shortstop for the Ravens. In 1998, he received a bachelor's degree from Merrimack College in North Andover, Massachusetts. At Merrimack, he was active in the Onstagers, Merrimack's student theater organization. He also played varsity baseball for the Warriors baseball team. During the summers of his college years, he was active in the training programs at the Williamstown Theatre Festival in Williamstown, Massachusetts. In 2014, he received an honorary doctorate in performing arts from Merrimack, where he also delivered that year's keynote address.
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