Joseph A. Critchfield McCray O'Toole, 31, of Charlottesville, VA, transitioned peacefully into eternal rest on Saturday, December 24, 2023. He was born on August 17, 1992, in Charlottesville, VA, to the late Phillip C. Critchfield Jr. and the late Melissa J. McGuire. He is survived by: Mother Brenda Allen McCray; brother Christopher T. McCray & family; sister Amy Haney & family; his grandparents Barbara Ice Rae & Phillip C. Critchfield Sr; Trish "Mom" McGuire & Timothy Manzi. He was preceded in death by his grandfather, Michael J McGuire. He leaves his devoted fiancé & soulmate Amber Kristina Roberts. Joseph adored his many aunts, uncles, cousins, nieces, and a nephew. He shared a special bond with Uncles Gene O'Toole & Mike McGuire, and Aunt Irene Manzi. He will be missed by his treasured friends. A graduate of Albemarle High School, Joseph was a member of the St. Marks Lutheran Church Chess Club, was a dry medium fine artist, and enjoyed reading philosophical authors such as Marcus Aurelius and Henry David Thoreau. He had an eclectic, sophisticated taste in music and fashion, loved animals, and was a rock & crystal hobbyist. He was often seen skillfully skate boarding throughout the city. He attended Cross Life Community Church in Charlottesville and was employed by James River Grounds Management of Charlottesville. The family extends deep gratitude to the Salvation Army & Cross Life Community Church. A Celebration of Life service will be held January 20th, 2024 at 11 am at Cross Life Community Church, 1410 Old Brook Rd, Charlottesville, VA . Attendees are welcome to bring meaningful tokens (rocks, crystals, etc.) to set on the memory table for the ceremony. A memorial event in New England for family & friends will be announced at a later date. An online guestbook is available at www.compassionatecremationva.com Compassionate Cremation Services of Ruckersville, VA, is handling the arrangements.