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Stephen Bailey
1959 - 2025
FUNERAL HOME
Stephen Bailey Obituary
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.
Memories and Condolences
for Stephen Bailey
Sponsored by Simpson Funeral Home & Crematory - Peters Creek Road.
1 Entry
Dutch Holland
October 21, 2025
So sorry to hear of Steve's passing. We had some great times in Hilton Head back in the day. He will be missed.
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Funeral services provided by:
Simpson Funeral Home & Crematory - Peters Creek Road5160 Peters Creek Road, Roanoke, VA 24019-3810
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