Surrounded by family, instructors and longtime friends of the aviation community, Bell took to the skies alone for the first time at the annual gathering, an accomplishment many pilots remember for the rest of their lives.

“It’s pretty cool that we get to both do it on the same fly-in,” Bell said, noting that his twin brother Isaac is also working toward his own solo flight during the event. “This is our family vacation, so being able to do it here is pretty unique.”

A first solo flight is a defining moment for any pilot. After demonstrating the skills and judgment necessary to safely operate an aircraft, a student pilot is cleared by an instructor to fly alone. For Bell, the achievement came after years of growing up around airplanes.

“My family’s been flying single-engine airplanes since before I was born,” he said. “My whole life, both my dad and my mom have been pilots.”

LAURA TARANTELLA/FOR THE EXPRESS Friends and family came out to show their support for Caleb, including members of the Bell, Newel, Baughman, Gilbert, Kehrer, Ridilla and Walker families.

The aviation heritage runs deep for the Bell family who has attended the fly-in for more than two decades, a tradition his mother grew up with as well.

“We’re fourth generation coming,” family member Amanda explained, jokingly adding how “next year maybe we’ll be bringing the fifth generation.”

Bell’s father said Caleb is the second of his sons to complete a solo flight at Sentimental Journey.

“It was good,” he said. “Our older son, Jacob, soloed here during COVID, so this is our second son to solo here. It’s fun to see it.”

The Bell family, who are from the Hershey area, have built much of their lives around vintage aviation. They regularly attend fly-ins and aviation events throughout the region, including World War II Weekend in Reading, Pa. and aviation gatherings such as Oshkosh.

LAURA TARANTELLA/FOR THE EXPRESS Caleb Bell shakes hands with one of his instructors Craig Kehrer.

“Our family just revolves around vintage aviation,” Bell said.

That passion for aviation history has shaped his own goals as a pilot. While many young pilots may dream of airline cockpits, Bell is drawn to historic aircraft.

“I like flying historic airplanes,” he said. “I like the history behind it.”

Looking ahead, Bell hopes to one day fly for the Golden Age Air Museum, an organization dedicated to preserving and flying aircraft from the early days of aviation.

“I would like to fly for the museum eventually,” he said.

The solo flight was made even more meaningful because it took place at Sentimental Journey, where many of Bell’s mentors and instructors were present to witness the achievement.

“All of our flying mentors are always here,” Bell said. “Just having them here to see it is really special, you know.”

For a young pilot raised in a family where aviation spans generations, the moment represented both a personal accomplishment and the continuation of a legacy that shows no signs of slowing down.

As another Bell family member prepares for a solo flight and future generations wait in the wings, the family’s connection to aviation — and to Sentimental Journey — continues to soar.