They fly like a dream, but not like the word usually means – not a smooth, comfortable, ride with drink service and a lavatory. To fly in a Boeing Stearman biplane is to live a kid’s dream of breaking the simple rules of gravity and feeling the wind on your face as you do loops in the sky, “hammerheads,” and a “Cuban 8.”

Matt Losacker, the right wing position of the four-plane Red Baron Squadron, uses the same friendly tone of voice to explain emergency procedures as he does the history of air shows. He points to his ripcord.

“If for some reason I say, ‘bail out, bail out, bail out,’ you are going to have to jump from the plane and pull this cord,” he said. “Now it’s not as easy as it looks. The plane will likely be traveling 120 miles per hour or more, in a free fall …”

“And don’t forget to take off your headgear. It’s connected to the plane,” he said.

Minutes later, the plane lifted off, a light and sudden departure from the earth. The engine let off whiffs of gasoline as Mr. Losacker pushed the throttle. It was like flying a souped-up Model T through the sky. The other planes were so close that lead pilot John Bowman’s silver mustache was visible beneath his aviator goggles.

Barreling toward the Long Island shore near the airport in Farmingdale, N.Y., Mr. Losacker patched through the intercom: “How are you feeling?” he asked. With affirmative nods or thumbs up from the four passengers, one in each plane, the pilots took their cue from Mr. Bowman. “Let’s go,” he said over the radio, and the planes did a quick dive before the pilots pulled back hard on the stick. The clouds slipped under the plane and the passengers’ guts went with it.

The red-and-white planes can reach 186 miles an hour, but they rarely go past 150 or 160. Even after having tumbled through hundreds – maybe thousands – of loops, barrel rolls, and other maneuvers, Mr. Losacker, one of the youngest pilots on the squad at 31, said he never gets tired of it.

“You couldn’t do it this much if you didn’t like it still,” he said. “I love it. Every time.”

Growing up watching his father fly commercial airplanes, Mr. Losacker said he wanted to be a pilot since he was a young man. The prospect of flying a Stearman – “the Cadillac of the skies” – with the Red Baron Squadron was a job that was easy to say yes to, he said.

True to the “barnstorming” tradition, the group will visit 80 cities this year and fly in 23 air shows. The pilots fly the planes from town to town, stopping about once every 90 minutes to refuel.

The Stearman, known as the PT 17 to the Army and the N2S to the Navy, was originally designed as a training plane for pilots during World War II. The only difference between those planes and the ones the Red Squadron fly is the engine. The modern version, a 985-cubic-inch Pratt & Whitney, has about double the horsepower of the original plane, but they use the same rugged frame.

After the war was over, the Armed Services had trained more pilots than there were commercial jobs available. But some pilots weren’t eager to give up their flying careers, so they bought old planes and flew them from town to town, seeking a little in the way of compensation for aerobatic entertainment. Approaching the town, they would first pull off an impressive move over Main Street before landing in a field near a barn. With a little luck and if money wasn’t too scarce among the townspeople, they would “storm the barn” and pay for rides in the plane.

The air show holds an unparalleled position in American life. Part military demonstration and part aerobatic spectacle, the shows bring in thousands of visitors during the summer months at cities across the country.

On his way out to test his Pitts Special biplane yesterday, an Air Force Reserve pilot, Ed Hammill, said the air show is a timeless thing.

“People who fly these airplanes are finding their dreams,” he said. “And there’s always been something intriguing about aviation.”

The plane’s chief mechanic, Matt Boehm, 24, added, “People are always inspired by things they can’t do.”

Looming behind Mr. Hammill’s small red, white, and blue biplane was a bright red Polish-made MIG 17, built in 1959. Though sponsored by Red Bull, the plane had a fresh decal of the Soviet hammer and sickle.

Countries as far away as the United Arab Emirates and New Zealand host air shows as well, though a massive accident in Ramstein, Germany, in 1988 led the government there to ban them outright. Three Italian air force jets collided in midair, killing the pilots and 67 spectators. The worst accident in history happened in 2002 in Lviv, Ukraine, when two planes crashed and killed 87 on the ground. Strict rules prevent planes from flying too close to spectators in America.

For Mr. Losacker, air shows are perfectly safe as long as pilots think of what they are doing as maneuvers and not stunts. With the Stearman – a plane that’s slower, “loopier and swoopier” than the other aircraft, he said – the key is never to take an eye off the lead pilot.

The planes travel as close together as the distance between the two sets of wings.

“You have to be able to read [the other pilot’s] mind,” Mr. Losacker said.

The New York Air Show at Jones Beach will take place on May 27 and 28. The event has free admission, but parking costs $8.