Roy was born in Haines, Alaska but grew up in the midcoast area of Maine. After college he spent several years working as a musician, traveling and living in Austria, Texas, Wyoming, and finally back in Maine. This is where he began working with youth at an arts-based summer camp, teaching music and wood-working. He spent the better part of the next decade continuing this work with teenagers in the mental health, education, enrichment, and career readiness fields. Roy joined Tree Street in 2022 to help launch the PINE Program, assisting young people with learning new skills to be successful in their work and career goals.

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