Mike Creato never thought he’d be anything other than a pilot. Growing up on his grandfather Stephen C. Gentle’s airfield in Katama, everyone he knew flew planes either for a living or in their spare time.

“Supposedly one of the first words I learned was an airplane word,” he said.

The owner of the biplane ride service Classic Aviators, Creato has spent nearly thirty years and more than 20,000 hours in flight. Although he learned the ways of the wing from his grandfather, a World War II–era flight instructor, Creato’s first exposure to his now-signature biplane got off to a rocky start.

His friend, Scott Chalice, had told him he always wanted a Waco UPF-7. Lo and behold, he had found one.

“It landed in a huge cloud of dust,” he said. “And then we started flying it.” 

The Waco, although relatively easy to fly, is notoriously difficult to land because of its front-heavy weight distribution. When Creato’s grandfather received a shipment of ten Wacos at military flight school, only one plane survived the weekend of test flights. Bolstered by the soft landing pad of the Katama grassland, Creato and Chalice mastered the biplane in about a week.

“I think [my grandfather] was surprised to see us in one piece,” he said with a laugh.

Over time, Creato bought two bright-red biplanes of his own to build his business. Now, he flies out every clear day between May and October, taking customers to observe the sights of the Vineyard from an aerial view. For the strong of stomach, Creato can heighten the experience with optional “aerobatics,” performing barrel rolls and loop-de-loops for riders’ and spectators’ enjoyment. 

When asked how he learned the high-octane party tricks, Creato gets slightly bashful. “It’s embarrassing,”he said. “I had a book.”

A thousand feet in the air, Creato tried out each trick on his own until he got it right, using his reference book on the ground in-between test flights.

“There’s almost no incidents of someone breaking a Waco mid-flight,” he assured.

Incidences of motion sickness, on the other hand, have been occasionally, albeit rarely, reported – mostly from his male clientele. “The women and children will tell you if they don’t feel good, but the men will try to force it back,” he said.

On the other end of the spectrum, Creato said he’s seen customers return years later to show him their pilot’s license, inspired by a memorable ride in the biplane. “Sometimes, you’ll get a more adventurous person who has brought along a more timid person,” he said. “By the time they come down, it’s [the timid person] who is the most exhilarated and excited, because they made it past that fear.”

Creato, for his part, finds solace in the clouds. “It’s the quietest, most peaceful place there is,” he said.

Standing out in the Katama Airfield, now owned and maintained by the town of Edgartown, Creato paused to observe the barn swallows flying overhead. They used to make nests in the hangars, he said, but now they just pass through.

“I marvel at the birds. I’m jealous of them,” he said, his eyes still up toward the horizon.