Flying Matters: Above the Clouds Brings Hope

At a time when general aviation is searching for ways to increase the pilot population (particularly of young men and women) and to “give back” to local communities, Above the Clouds emerges to accomplish these goals.

As Sean Cudmore stepped onto the tarmac and beheld the fixed-gear Saratoga, his eyes lit up with excitement.

“Just look at that!” he said as he pointed to another airplane touching down on the runway. “I’m going to be actually doing that in a matter of minutes!” Sean, like many other children and teens before him, was about to embark on a Dream Flight.

Above the Clouds, a Boston Area non-profit charity recently founded by Executive Director Gary Oberstein, is committed to spreading joy and hope through the wonder of small aircraft flight.

One of the charity’s two programs is the Dream Flyers program, in which volunteer pilots donate their time and their small aircraft to provide seriously ill, disabled, and underprivileged children a day of fun. “It’s all about making a really exciting day for kids who may not otherwise have too much fun in their lives,” said one volunteer.

Every weekend during spring, summer and fall, Above the Clouds gives children like Sean a chance to soar high above their problems. Leaving behind a smiling crowd of friends, family, and volunteers, the whole world stretches out beneath the Dream Flyer. Dream Pilots fly over the child’s home and significant landmarks before passing the controls over and giving the Dream Flyer the opportunity to fly the plane.

As he climbed out of the airplane, Sean described the experience: “I saw everything … like trees and all of the shapes of how everything went together … the pools. It was really cool!”

Then it’s off to the pilot’s lounge where refreshments are served and one last surprise awaits. After flying, every Dream Flyer is presented with their personalized flight jacket and aviator sunglasses. Although the jacket is a bit too warm to wear during these hot summer months, come winter, there will be dozens of Dream Flyers sporting their flight jackets. Every time they wear it, they can remember their special day and hold their heads a little higher.

In addition to the Dream Flyer Program, Above the Clouds runs the Cadet Flyers Program, in which underprivileged youth have the opportunity to learn to fly. Cadet Flyers work with an Above the Clouds volunteer Certified Flight Instructor and embark on a challenging journey, culminating in their first solo flight.

Brendan Feitelberg, an Above the Clouds Board Member, described the program: “It gives an amazing opportunity to children who could never otherwise dream of doing a program like this. It builds confidence and gives them the ability to say ‘I can do anything.’”

For the Cadet Flyers Program, Above the Clouds reaches out to teens stuck in tough neighborhoods and failing schools. Boston public schools currently have a dropout rate of over 34 percent, often accompanied by a youth culture that has lost faith in the value of education. The Cadet Flyers Program serves as a motivational tool to keep these teens on track for success. In addition to learning how to fly, Cadet Flyers make a pledge to stay in school, and they learn first-hand how studying and hard work can pay off.

While only in its first year in operation, Above the Clouds has already touched many lives. Gary Oberstein, Above the Cloud’s founder and executive director, is an employment attorney, the managing partner of Nixon Peabody’s Boston office and an instrument-rated pilot. Above the Clouds was born out of his desire to pair his passion for aviation with his wish to help kids in need. Gary, together with a growing number of volunteer pilots, committed board members and caring volunteers, donates his time, passion, and enthusiasm to ATC’s Dream Flyers and Cadet Flyers.

Delighted to see first-hand the impact on his young Dream Flyers, Gary finally said, “Joy as medicine is something that is pretty well documented, and when the day comes to go up there, they [the Dream Flyers] just have a phenomenal time.”

Thanks to Above the Clouds and its sponsors, kids and teens are benefiting from the power of motivation, excitement, and infectious joy that comes from learning just how high they can fly.

In our Flying Matters series, we focus on the great work being done by aviation-related non-profits and charitable organizations. To help contribute to our series with your organization, please contact us at


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