WWII veteran Chester Milton (left) rides in front of Dream Flights pilot James Sims, just before they take off for a flight over Caribou. Credit: Hannah Catlin / Aroostook Republican

CARIBOU, Maine — Gliding high over the fields and houses of Caribou, four World War II veterans took turns flying aboard a 1942 Boeing Stearman on Tuesday afternoon.

The youngest people who served in the war are now in their mid-90s, and the flights paid tribute to the Greatest Generation’s sacrifices for the United States.

One-by-one, the veterans climbed into the front passenger seat of the open-cockpit plane, and took half-hour flights with volunteer pilot James Sims.

Sims and fellow pilot Eric Mueller work with Dream Flights, an organization that travels across the country with similar antique planes giving rides to veterans of the Vietnam War, Korean War and World War II.

Dream Flights pilots Eric Mueller and James Sims have traveled across the country in this refurbished 1942 Boeing Stearman, giving rides to veterans of WWII. Credit: Hannah Catlin / Aroostook Republican

Like most of the pilots with the organization, Mueller and Sims usually fly for commercial airlines, and have undergone special training to maintain and fly the 80-year-old plane. They’ve taken two months off from their regular jobs for a program called Operation Freedom — during August and September, Dream Flights is just flying WWII veterans.

During the flights, Sims followed the veterans’ directions as they pointed out houses, schools and churches they wanted to fly over.

As they landed back at Caribou Municipal Airport, each veteran signed the bright blue tail of the plane, which will fly to Hawaii in December to commemorate the 80th anniversary of Pearl Harbor.

Chester Milton of Caribou served in England and Germany as a medic assigned to a B-17 Army Air Corps group, and rode in the Stearman on Tuesday. Flying in a plane like this was on his bucket list — he was 9 years old when he last rode in an open-cockpit plane, he said.

“Just the sight of it caught me,” Milton said.

Dream Flights pilots Eric Mueller (left) and James Sims (right) pose with Chester Milton after landing. Credit: Hannah Catlin / Aroostook Republican

Milton took flying lessons at Caribou Municipal Airport in the 1930s when he was a teenager. A lifelong aviation enthusiast, Milton joked he was leaving with Sims and Mueller at the end of the afternoon. He has continued to paraglide and ride in hot air balloons and is planning another paragliding trip before he turns 98 in November.

“This made my day,” Milton said. “You don’t know how much better it looks from up there.”

Milton’s daughter, Sharon DeMerchant, said that her father has been thrilled about the opportunity since he found out the day before that he would be flying, and will probably talk about the flight for the years to come.

“All growing up, Dad never ever talked about the military, never talked about anything,” Demerchant said. “It’s only in his later years that he started sharing and talking about things that he saw and experienced. And he just loves planes. Something stuck with him. I guess we all have those things that will always mean something to us.”

Alongside Milton, Dream Flights gave rides to Lester Martin — a 93-year-old veteran who enlisted when he was just 17 — Peter Darling and Herbert Learnard. All of the veterans were from Caribou, except for Leanard, who lives in Van Buren.  

Herbert Learnard, a veteran of WWII laughs as he climbs into the Stearman biplane for a flight over Caribou. Credit: Hannah Catlin / Aroostook Republican

“[I saw] the whole town of Caribou, and I think New York,” Learnard said. “That was good, that was really good. I was just scared he was going to roll it over.”

Mueller and Sims are just two of Dream Flights’ roughly 30 volunteer pilots. The pair have been traveling the eastern United States since the beginning of August, flying between locations in the Stearman. After Caribou, they’re heading to New Hampshire.

“It’s easily the most significant experience of my life … it’s the last time in all of our lives to meet these guys,” Mueller said. “Coming to Caribou and getting to meet Chester and Peter and Lester and Herbert has been an amazing honor. Compared to what they did, I haven’t had a hard day in my life.”

Sims comes from a family of veterans, and said that working with Dream Flights has been the best way he has found he can give back to those who served.

During his time with the organization, he has met veterans who have worked in all branches of the military and in dramatically different capacities — everyone from survivors of the U.S.S. Arizona, to soldiers who led battalions at 20 years old, to veterans of the Women Airforce Service Pilots.

Herbert Learnard signs the tail of the Stearman, which will fly to Hawaii this winter to commemorate the 80th anniversary of the Pearl Harbor attack. Credit: Hannah Catlin / Aroostook Republican

Across everyone he’s met, the veterans share a sense of optimism and gratitude — for life, community and family, Sims said. Landing at an airport and seeing five generations gathered together is always a special moment.

“You don’t [just] hear grandpa. You hear dad, grandpa and ‘go say hi to great grandpa,’” Sims said. “For me those are the special moments, when we get to bring families together and give them some lasting memories.

“It’s the greatest honor I could ever ask for.”

Hannah Catlin

Hannah Catlin is a reporter at the St. John Valley Times/Fiddlehead Focus in Madawaska, Maine.