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'True legend' Chuck Tippett remembered

Tailwheel instructor, wing walker, airport owner had a heart of gold

Hall of Fame inductee, wing walker, and Horse Feathers airport owner Charles Stanley “Chuck” Tippett, 65, whose impact on aviators in Maryland, Virginia, and the Washington, D.C., area was substantial, died August 3 in an eastern Virginia boating accident.

Charles "Chuck" Tippett flew a 1927 Travel Air during a Flying Circus Airshow performance in 2020. Photo by Chris Rose.

Many students said he quickly gained their confidence with a smile and a hearty laugh, and that Tippett never really met a stranger. He taught scores of pilots, including his grandkids, to fly tailwheel aircraft with at least one former student going on to establish a tailwheel-only flight school.

Tippett performed as a wing walker without safety lines or harnesses and instead clenched his ankles around a biplane wing strut—often hanging upside down, as noted on his Virginia Aviation Hall of Fame induction page in 2016. Among other accomplishments, he was recognized for decades of dedication to aviation and as a pilot and a performer for the Flying Circus Airshow in Bealeton, Virginia; for his love of vintage aircraft; and for his volunteerism with the Wounded Warrior Project and the Make-A-Wish Foundation.

The Midland, Virginia, commercial land and sea pilot recently held several fly-ins at his 3,000-foot grass landing strip nestled in the rolling hills close to Warrenton/Fauquier Airport just outside of the busy Washington, D.C., Class B airspace. 

A well-attended May event with food trucks, dance performances, and bands helped raise funds for the Virginia Aeronautical Historical Society. Tippett followed it in June with a weeklong paraglider workshop culminating in a live music and food truck fly-in to honor his retiring friend, United Airlines pilot Gail Keys. After those successful events, Tippett had planned to hold additional fly-ins, training workshops, and celebrations on the manicured airfield that he called “one of the finest grass strips in America.”

Virginia Hall of Fame inductee, wing walker, and Horse Feathers airport owner Charles Stanley "Chuck" Tippett, 65, died August 3 in a boating accident. Photo courtesy of Warrenton-Fauquier Airport.

The electrical lineman owned and operated 11 aircraft. After specializing for years in taildraggers, vintage aircraft, and biplanes, Tippett said he recently “got into the lowest common denominator of flying” by learning to pilot a paraglider. 

To the delight of younger aviation enthusiasts, the silver-haired, mustachioed Tippett often appeared at aviation events in distinctive knee-high, lace-up leather boots and a throwback long-sleeved white shirt reminiscent of aviation’s Golden Age.

The Flying Circus published a tribute recognizing two decades of Tippett’s time dedicated to the organization, calling him “a cornerstone” and one of the group’s “brightest stars” for his vintage airplane flying and freestyle wing walking antics that enthralled and inspired visitors. “If you had the pleasure of meeting him, you likely heard him before you saw him,” the organization wrote. “Chuck was, and always will be, a true legend in the aviation community.”

He was also a good friend to the Warrenton/Fauquier Airport with its active aerobatic community and bustling training area just 5 miles south of Tippett’s farm field.

“Chuck Tippett never met a stranger,” said Warrenton Airport Manager Stacey Williams. “He was one of the most generous people I’ve ever known—not just with what he had, but with his time. He didn’t do it for recognition or praise; he did it simply because he cared about people. His attitude and laughter were infectious.”

Retired U.S. Air Force pilot, charter pilot, and general aviation pilot Heather "Lucky" Penney, left, and retired airline captain, author of "Jet Boss," chairman of the Virgina Chapter of The Ninety-Nines, and GA pilot Laura Savino, right, pose for a picture at a fly-in to the Horse Feathers grass airstrip. Photo by David Tulis.
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Retired U.S. Air Force pilot, charter pilot, and general aviation pilot Heather "Lucky" Penney, left, and retired airline captain, author of "Jet Boss," chairman of the Virgina Chapter of The Ninety-Nines, and GA pilot Laura Savino, right, pose for a picture at a fly-in to the Horse Feathers grass airstrip. Photo by David Tulis.
A biplane lands at the Horse Feathers grass airstrip. Photo by David Tulis.
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A biplane lands at the Horse Feathers grass airstrip. Photo by David Tulis.

Tippett was also eager to help when something needed to be done around the airport. Williams was impressed with his ingenuity changing out the light bulbs on the streetlamps high above the ramp. “The light poles were 90 feet tall, but his bucket truck only reached about 50 feet. For Chuck, it wasn't an issue. He'd ride the bucket up, climb the remaining 40 feet, wrap one arm around the pole, change the bulb, and carry on a conversation the entire time as if he were standing on the ground.”

Virginia Hall of Fame inductee and Bealeton Flying Circus wing walker Charles Stanley "Chuck" Tippett performs a freestyle wing walking routine from a biplane. Photo courtesy of Warrenton-Fauquier Airport.

Tippett also helped remove the airport’s old rotating light beacon in 2013 so it could be preserved. “It took 13 years, but this year we were finally able to finish the preservation, and we now proudly display the beacon in our terminal,” Williams said. 

Fredericksburg, Virginia’s Shannon Airport reminded social media followers that the tailwheel specialist was called upon to make the first flight of Shannon Air Museum’s Piper Cub after it had hung from the ceiling of the Virginia Aviation Museum in Richmond for more than 40 years.

Virginia aviator and Fuji LM-1 warbird pilot Phil McLanahan said Tippett was “amazing.” When a pair of pilots and their dog needed a lift from Horse Feathers’ grass airfield back to an airplane ramped at the paved Warrenton airport, Tippett sprang into action by flagging down McLanahan with a wave and a smile—and that’s how fellow aviators remembered him—always ready to lend a hand. “We were great friends and I’d just emailed him to do some formation flying last week. It’s a huge loss.”

Maryland pilot Miguel Garriga credited Tippett with making him feel at ease during tailwheel instruction before they became fast friends. “Chuck was very giving. He loved aviation and I know he touched many lives,” recalled Garriga. “He showed his gratitude [to other aviators] by introducing hundreds to aviation and personally instructed more than 150 flight students.”

Several weeks ago, Tippett brought Garriga a model airplane with a seven-foot wingspan so youngsters at the family’s day school could play with it and learn about aviation. “He was just passionate about anything flying. It’s a great loss for aviation in our area,” said Garriga.

Pilots perform a two-ship flyby over the Horse Feathers grass airstrip in Virginia on May 2, 2026. Photo by David Tulis.
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Pilots perform a two-ship flyby over the Horse Feathers grass airstrip in Virginia on May 2, 2026. Photo by David Tulis.
David Tulis
David Tulis
Senior Photographer
Senior Photographer David Tulis joined AOPA in 2015 and is a private pilot with single-engine land and sea ratings and a tailwheel endorsement. He is also a certificated remote pilot and co-host of the award-wining AOPA Hangar Talk podcast. David enjoys vintage aircraft and photography.
Topics: People

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