Middleton Moments

Our dad, Gary Middleton, was more than a father—he was a mentor, a dreamer, and a man who made every moment count. While we will miss him deeply, we find comfort knowing his spirit lives on in the moments he created and the lives he touched. His passion, his lessons, and his unwavering belief in lifting others up will always be a part of us. Through Middleton Moments, his legacy continues—bringing hope, joy, and new possibilities to those who need it most, just as he always did.

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Where It Started -

Flying Changed His Life

Flying changed my dad’s life. After serving in Vietnam, he used the GI Bill to earn his pilot’s license, spending every possible moment at the airport—even sleeping on parachutes so he could be in the air every waking moment. He quickly earned his ratings and began flying DC-3s to deliver freight before launching his commercial career with Air Wisconsin. Over the next 50 years, he piloted more than 125 different aircraft, logged over 29,000 flight hours, and lived a lifetime of adventures—each one turning into a story worth telling. Aviation didn’t just take him places; it gave him opportunities he never imagined possible.

His Dream -

Hope Through Aviation

Throughout his life, my dad was the kind of person who gave to others, even when he had little to give. From serving as a medevac in the military to rendering aid at car accidents to help strangers or quietly buying meals for the homeless, he believed life was about the moments we create through kindness. As a flight instructor, he trained countless pilots and introduced thousands of people to the possibilities that aviation could bring. But his greatest joy wasn’t just flying—it was sharing it. He loved parking his plane, talking with families, and offering rides, often letting kids take the controls. His favorite stories weren’t about the flights themselves, but about the smiles, the wide-eyed wonder, and the pure joy expressed in those moments.

Our Mission -

Hope in Every Horizon.

We will be working with the incredible aviation community and the lifelong friends my dad made throughout his career to create moments of joy for families who need them most. Through schools and public outreach, we will identify kids going through tough times—those who need a win, a spark of happiness, or a light in the darkness.

Seeing the world from the air in a small airplane isn’t just exciting—it’s peaceful, beautiful, and unforgettable. We’ll pair these kids with some of the best pilots in the area, renting an hour in the sky to give them an experience they might never have had otherwise.

But we don’t want to stop there. Our ultimate goal is to provide resources, mentorship, and even scholarships to help those inspired by flight pursue careers in aviation. It changed my dad’s life, and our hope is to help others find their own path to the skies.

Donations -

Creating a Moment

There are many ways to support Middleton Moments beyond monetary donations—whether it’s giving your time, spreading awareness, or simply keeping us in your thoughts, every gesture makes a difference.

Middleton Moments is currently incorporated and awaiting 501(c)(3) approval. Once approved, all donations will be retroactively tax-deductible, and we will provide the necessary documentation for your records. Your support, in any form, helps keep my dad’s legacy alive and brings joy to those who need it most.