At one of the Imperial War Museums in Duxford, England, military airplanes are displayed alongside vignettes about the service members who flew and maintained them, said Jeff Boyling, a patron of the museum who part-owns a World War II-era amphibious aircraft, the PBY Catalina.

The Catalina conducted reconnaissance for the Royal Canadian Air Force during the war; and now Mr. Boyling and others take it around the world so people can sit in it, see it fly and learn about its exciting past. “It carries a heavy responsibility, making sure people are educated,” Mr. Boyling said.

The impact of seeing these airplanes fly should not be underestimated, said Dean Alexander, tour coordinator for the British Aviation Enthusiasts Society and former superintendent of the Dayton Aviation Heritage National Historical Park.

The D-Day Squadron’s trans-Atlantic crossing is a great example of that. That flight was “very likely one of the first times many of these people have seen a World War II airplane except in the movies,” Mr. Alexander said. “It could have a similar effect to Wilbur Wright flying up and down the Hudson. That was the first time most people would have seen an airplane.”

Mr. Fleishman, the young pilot and an aspiring mechanic, is a notable ambassador for keeping the legacy of these planes alive. Several days before the squadron left the United States, Mr. Fleishman, dressed in his flight suit, guided a group of 50 students from Connecticut’s Nonnewaug High School around the airport, telling them about each airplane.