Henry A. Trail
Henry Allen Trail, 83, of Roanoke, VA drifted away peacefully on September 1, 2026 with his daughter and son in-law by his side.
Henry was born March 7, 1943 in Buchanan, VA. He was the second eldest child of the late Viola Simpson Trail and Henry Woodson Trail. He was also preceded in death by his wife of 58 years, Barbara “Bobbie” Trail; brother Rodney Trail and sisters Mary Hollingsworth, Doris Jones and Janie Teaford.
Left to cherish Henry’s memory is his daughter, Jennifer Trail Gaddy and husband Chad; sister, Shirley Amos; sisters in-law Linda Trail and Kristie Claytor (Charlie); brother in-law, Mike Teaford; grandchildren, Haylynn Gaddy (Brauxton), Ashlynn Gaddy (Parker) and Tyler Gaddy. He is also survived by nieces Rana Claytor Buchanan (Dean), McKayla Hoke (Seldon), Tammy Teaford Cobb (Roger), Marcy Rickman Martin and Becky Teaford Rowland (Ronald); nephews Jeff Hollingsworth (Heather), Donnie Rickman (Josey), Tony Rickman (Kristin) and Michael Hoke (Amy); great-nieces and nephews Autumn Hollingsworth Roberts (Nathan) and Justis Beverly, as well as other extended family.
Henry served in the US Army in the early 1960’s, stationed in Manheim, Germany. He had many fond memories of his service and loved to talk about it to anyone who was willing to listen. Following Henry’s Army career, he & Bobbie were married May 18, 1968 and they made their home in Roanoke, VA. Henry began his working career at Sav-A-Stop becoming Merchandising Director and worked there until its closure in 1987. He moved on to Moore’s Lumber & Building Supply/The Contractor Yard corporate office in the Purchasing Department and went on to manage the Door Shop, retiring in 2008. Following his retirement, he chose to work part-time at Advance Auto as a PDQ Driver for his “fun money”. Henry & Bobbie were members of Trinity United Methodist Church in Roanoke, VA for many years until its closure.
Henry was a wonderful man, he was admired and loved by many and touched a lot of lives during his 83 years. He was truly one of a kind, there aren’t enough words to describe the gentle and thankful man he was. He could make, fix or do just about anything. He gave freely and was always willing to help others. Henry enjoyed hunting and fishing with his brother, Rodney. They spent countless hours on the James River and in the woods of Buchanan. He was savvy with antique cars, rebuilding a 1957 Chevrolet Bel Air and a 1946 Ford. He & Bobbie held season tickets for Virginia Tech football games, they loved tailgating with friends and rooting for the Hokies. In his retirement years, Henry found great joy in playing golf with his bother in-law, Chester Hollingsworth, and he was quite good at it! There are rumors of nickel bets being made at each hole, I guess we will never know the truth or whose pockets jingled the most when leaving the course.
Those that knew Henry, knew that Jennifer was the brightest light in his life. They spent a lot of time together while she was growing up and had a strong Daddy/Daughter bond until he breathed his last breath. He danced with Jennifer in the den and painted her nails whenever she asked, he was proud of being a Girl Dad. He took her fishing, snow skiing and riding around in the snow laughing while he did donuts in Mt. Pleasant Elementary School’s parking lot. He attempted to teach her how to ride a bike, unfortunately that didn’t work out very well despite his efforts. He also taught her to drive, exercising great patience during that process. One very special thing that Henry began doing the year Jennifer turned 16 was buy her flowers on Valentine’s Day, that continued without fail for 29 years. He had bought Bobbie flowers every year and decided that he couldn’t leave Jennifer out. The best memories were made during the annual family beach trips that began in 1979. Henry was the fun Dad, playing in the ocean and pool for hours on end and building “drip” sandcastles with Jennifer and Rana when they were children. There are endless stories from these trips that will never, ever be forgotten.
A heartfelt thank you to chosen family members, Trinity Bess and April Fitzwater, for their unwavering support and willingness to help anytime it was needed. Henry & April developed a special bond, she took him down memory lane to Willie Ransone’s Drug Store in Buchanan for a hot dog and on adventures to the Mill Mountain Star and Zoo, the Transportation Museum and just riding around to look at the mountains in the distance. The family would also like to thank the staff at Our Lady of the Valley’s Sullivan Center for their loving care during Henry’s final days.
The family will receive friends for one hour beginning at 10:00 am on Saturday, September 12th at Simpson Funeral Home 5160 Peters Creek Road, Roanoke VA. A Funeral Service will be held at 11:00 am, immediately following the visitation.
In lieu of flowers, donations are encouraged to be made in Henry’s honor to Parkway Church Vinton Campus at 246 Jefferson Ave, Vinton VA 24179 to support their Parkway Kids program.
