Don Shilling

Don Shilling’s Story

Don Shilling was born in rural southeastern Wisconsin in 1947. His father tragically passed away in an industrial accident in 1949, leaving Don without the chance to know him. His mother later remarried, and Don’s stepfather became a powerful and positive influence in his life. Don recalls him as “a great man.” Sadly, his stepfather also passed away in a fire in 1967, another deep loss that shaped Don’s journey.

After graduating high school, Don attended college for a couple of years before deciding to pursue a different path. In 1969, he joined the United States Army. Having always dreamed of flying, he successfully entered Army Aviation and trained as a helicopter pilot.

In 1970, Don deployed to Vietnam, where he flew both Hueys and Loaches. That same year, he participated in a mission attempting to extract the crew of a Cobra gunship that had been shot down. Multiple helicopters were involved in the battle, and during the operation Don and his entire crew were wounded. He was medevacked to Japan for treatment and eventually returned home.

Following his military service, Don attended aircraft mechanics school and built a career in aviation. He earned the necessary certifications and went on to not only operate aircraft maintenance companies but also continue flying. Over the years, he piloted many different aircraft, a career that took him across the globe.

One of the highlights of his professional life was working with Connie Colletta, the well-known auto racer and owner of Colletta Aviation. Don describes their partnership as “a relationship made in heaven,” full of shared experiences and the satisfaction of building a strong business together.

Beyond aviation, Don lived life at full throttle. He raced motorcycles, go-karts, midget cars, and sprint cars, embracing the adrenaline and camaraderie of motorsports. His adventurous spirit also came with risks, leading to several injuries along the way. One particularly dramatic incident, the 1991 Don Shilling and Mike Mason Midget Car Crash at Winchester, can even be found on YouTube.

Despite hardships and close calls, Don considers himself blessed. “I’m still here,” he says, grateful for the gift of life. He has been married for 29 years, raised a family, and enjoyed a lifetime filled with adventure, family, and success.

Today, Don enjoys fishing, hunting, gardening, restoring cars and motorcycles, and—by his own admission—“spoiling” his wife. His story is one of resilience, passion, and gratitude.

At Bucket List Dreams, we are thankful for people like Don. He embodies the essence of a life well lived, and he represents exactly what we strive to celebrate. Don will be joining us for a pheasant hunt, and we are honored to recognize his service, his adventures, and the inspiring life he continues to lead.