Ashley was born in Bennington Vermont and grew up between Bennington and Pownal. Immediately upon graduating high school he joined the US Marine Corps and was stationed primarily at Camp Lejeune, North Carolina. He was deployed to both Operation enduring freedom and operation Iraqi freedom. He was honorably discharged from the Marine Corps in 2004 and returned to Vermont where he became a trooper with the Vermont State Police.
Ashley then moved back to North Carolina where he began farming with his family and worked as an accident investigator with the Marine Corps Police Department. He currently works with the Postal Service in Wilmington, Vermont and runs a sustainable farm, Harwood Homestead with his wife Sarah, two sons Gavin and Bryson and daughter Iris.
Ashley is also the chair of the Farm Committee.