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With local charity, hope takes flight

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By Katrina Margolis
Hometown Weekly Reporter

Gary Oberstein brings hope and joy to children and teens who need it most through a most unusual way: the wonder of small aircraft flight. Entering their fifth year, Above the Clouds flies out of Memorial Airport in Norwood, offering children and teens who are ill, disabled, underserved, or facing other serious adversity an incredibly unique experience. After getting his pilot’s license, local charities or non-profits would auction off rides in Oberstein’s plane. When one woman won a flight, instead of taking it herself, she wanted a number of kids from the organization to be able to go up. The organization only grew from there.

“These kids have never been on a plane, had never been outside of Boston in their lives, never really had much of anything, and they reacted so wonderfully to this,” Oberstein said.

Above the Clouds is entering its fifth year and will hopefully continue to keep growing

Above the Clouds is entering its fifth year and will hopefully continue to keep growing

“One boy in particular, whose older brother was in a gang, he was in danger of dropping out, and he was nearing the age where he was going to be recruited by his brother’s gang.” This boy’s guidance counselors had been trying to get him to go to tutoring without any luck. However, a few weeks after his flight, he went to his counselor and said, “I went on this airplane ride and pilot Gary told me that if I wanted to become a pilot I’ve got to do well in school, so I guess I want to talk to you about that tutoring stuff you’ve been nagging me about.”

Oberstein was blown away. “All I had to do was fly him up in the air, to go and do what I do anyway and have fun! And here’s the possibility of turning this kid’s life around.”

Since then, Above the Clouds has grown to have 50 volunteer pilots who have provided well over 500 flights for 270 kids. The organization has three programs: Dream Flyers, Discovery Flyers, and Cadet Flyers. Dream Flyers provides a weekend of fun and excitement for kids. The most recent one took 16 kids up into the air. “We make them feel really special. Some of them don’t really get much attention at all, but we have a whole team of greeters, everyone is just screaming their name,” Oberstein said. “They get into the plane and they fly over the kid’s home, they fly over their hospital if appropriate, over Fenway, and Gillette. And then at the right moment, the pilot lets go of the controls and the kids fly. All of them fly. Some of these kids have never been in control in their lives and all of a sudden have this incredible control of an entire aircraft.”

Discovery Flyers is a mentor program for teenagers who have the opportunity to fly regularly as a co-pilot. Cadet Flyers is in direct response to the number of young people who are falling through the cracks at school or are involved with social service agencies due to poverty or at-home situations. These kids offers the missing motivational tool that will serve as the conduit to encourage these teens to stay in school, apply themselves, and hopefully have a better future.

For more information about Above the Clouds or to donate, visit

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