Fr. Woolley is a graduate of Coventry High School, Class of 1985. He earned his Associate's Degree in Engineering from Community College of Rhode Island in 1987, and a Bachelor of Science Degree in Civil and Environmental Engineering from the University of Rhode Island in 1990. For his theology studies, he earned a Master of Arts degree in Theology from Holy Apostles Seminary in Cromwell, Connecticut, in 1997 and a Master of Divinity degree in Theology from Mt. St. Mary’s Seminary in Emmitsburg, Maryland in 1999. Fr. Woolley was ordained by Bishop Robert E. Mulvee in the Cathedral of SS. Peter and Paul in Providence on June 26, 1999.