Stephen Bailey

1959 - 2025

Stephen Randolph Bailey

December 19, 1959 - October 12, 2025

Stephen Randolph Bailey, 65, passed away on October 12, 2025. Remembered as a beloved husband, stepfather, brother, uncle, and friend, Steve was known for his generosity, warmth, and adventurous spirit, leaving a legacy of love, laughter, and kindness.

Steve was a standout athlete at Lord Botetourt, excelling in football and pole vaulting, and a founding member of the Daleville Dirt Diggers motorcycle group. His love for sports continued throughout his life with a passion for fly fishing, golf, and enjoying the outdoors. He was always easy to recognize in his signature casual attire.

A proud Virginia Tech graduate, Steve built a remarkable 33-year career as an airline pilot, retiring from JetBlue. He was admired for his professionalism, calm demeanor, and dedication to perfecting his craft.

After retirement, Steve embraced daily life with joy-playing golf with friends at Blue Hills, working on his tractor, and exploring neighborhoods with his loyal dog Lakyn. He cared deeply for animals, including his other dog Harper, cats Bailey and Tortie, and the wildlife around his home.

Steve's generosity knew no bounds. He often mowed lawns for neighbors, bought "closer drinks" for restaurant staff, and offered help to strangers, family and friends never seeking recognition. His ability to forge friendships was unmatched, with many lasting since his childhood in Daleville. Steve's presence brought humor, steadiness, and warmth to everyone he met.

He is survived by his wife, Andrea Stetson; stepchildren, Matthew Sweeney (Madeline) and Meredith Craven (Brian); grandchildren, Ruby, Park, and Lillian; brothers, Richard, Michael, Dewey (Jim), Hal, and Bobby Bailey; and many beloved nieces and nephews. He was preceded in death by his parents, Dewey James Bailey, Jr. and Nancy Casey Bailey, and stepmother, Patty Bailey.

Friends are invited to share memories through the Forced Joy Project. Donations in his honor may be made to St. Jude's Children Hospital, Tunnels2Towers, or Angels of Assisi. A Celebration of Life will take place on December 19, 2025, in Troutville, Va.