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Leroy Barnstable’s life has been pretty uneventful until the year he turns fifteen – helping his dad with weekend auctions, playing ball with his school buddies, listening to his mom read aloud from a Dickens novel, practicing his drawing (friends have nicknamed him “Doodlebug”). All of that changes in 1922 when his father is killed and his mother seriously injured in an auto accident. The family farm is debt-ridden and, once affairs are settled, Leroy and his mother go to live with relatives in a nearby county. Leroy’s grown cousins, Albert and Virgil, own a livery stable and harness store in Cutter’s Creek and they waste no time in putting Leroy to work.

Over the following year, as his mother’s health continues to fail, Leroy chafes at the workload he has been given and the strict unloving discipline administered by his cousins. When his mother dies the spring he turns sixteen, he foresees that Virgil and Albert will likely make him leave school and spend his entire time working for them. He decides to run away, but not before he can retrieve at least some of the two hundred dollars (all that was left when the farm was sold) his cousins are keeping in a tightfisted trust. Following a good week of sales at the Livery store, Leroy filches half of what the brothers owe him and, borrowing one of their horses, heads out at night to Jackson Junction, the closest town with a railway – intent on getting as far away from the cousins as possible.

Stopping on the way for a rest, Leroy falls asleep, waking to find Albert has caught up with him and has reclaimed his horse. He is able to scuttle away through the brush, though, and later, when he reaches Jackson Junction, discovers a freight car being loaded with Chautauqua equipment on a railway sidetrack. He hides away, discovering that he has a traveling companion – an old hobo, Zach, who is also intent on catching a free ride. Soon the car is coupled to a freight and they are on their way. Zach fills him in on how a Chautauqua operates, employing a circuit of tents set up in towns for weeklong runs of programs.

When the freight reaches the town of Paradise, Leroy is poised, ready to jump off the car, but checking his pockets, he realizes Zach has stolen most of his money. As the car door opens, Zach leaps and runs. When Leroy attempts to follow and grab him, he trips on a coil of rope and falls headfirst onto the rail bed, in front of the waiting Chautauqua crew, spraining his arm. Robert Tremain, a Chautauqua character actor and his daughter Maggie, who manages the program for children, tend to Leroy’s arm and arrange for him to stay with the tent boys in their quarters while his arm mends.

His first day with the Chautauqua crew, Leroy, with his artistic ability, is able to make himself useful to Maggie, designing a backdrop, and later he sets up a drawing activity for the younger kids. Along with the tent boys, he takes part in the town parade, and is enthralled with the performances he is able to catch in the main tent – particularly Tremain’s impersonations and the concert given by the beautiful opera songstress, Clementine Cavallero. When his only set of clothing becomes soaked, Leroy – who has adopted the stage name “Doodlebug” – dresses (from Maggie’s costume box) as a tramp. His success as a vagabond artist spurs him to retain the costume whenever he is working in the tents or on the grounds. Maggie’s uncle, the portly superintendent Ambrose Poindexter, suggests he try his hand at doing crayon portraits for patrons willing to part with two bits – a way for him to earn some money since he’s not on wages.

His expertise as a portrait artist gains him a commission to draw a widow’s housecat at her home, an experience that leads to a hasty exit when the widow begins making overtures toward him. Returning to the Chautauqua grounds late at night, Doodle stumbles on an alleyway encounter between Maggie’s father and a thug – Sheamus — who is manhandling him and uttering threats if he doesn’t get the return of money that’s owed. If Tremain’s ladyfriend, Clementine Cavallero, can go about dripping jewels, they can pay him off. Leroy wonders if Maggie knows the trouble her father is in – and he wonders if there is some connection to Maggie’s having needed expensive eye surgery a few years back.

Over his weeks with the Chautauqua, Leroy has become increasingly smitten with Maggie but he finds himself vying for her attention with Scotty, one of the handsome college boys working on the tent crew. When a drunken Sheamus shows up just after an evening show and seizes Maggie, though, it is Leroy who quick-wittedly grabs a prop gun and manages to get him to back off.

At the last town on the summer circuit, Leroy sees Albert on the prowl for him, but he decides to remain with the Chautauqua, hoping that Albert won’t find him in his vagabond disguise. A fierce thunderstorm batters the tent during the evening show, knocking out the electricity, but the crew quickly lights lanterns so the performances can continue. This is the evening when Tremain does his impersonations and a jewel-bedecked Clementine is also performing. Sheamus surfaces and, once the audience has exited the tent, he attempts to snatch Clementine’s jewels off her. Tremain comes to her rescue and, in their scuffle, a lantern is knocked over.

The tent catches fire. Everyone manages to get out except for Sheamus who trips, hits his head against the stage, and falls unconscious. With a length of rope in hand, Leroy goes back into the burning tent and knots the rope to Sheamus’s belt loops so the tent boys can drag him out. Albert and the sheriff have arrived on the scene, but the sheriff warns Albert to leave Leroy alone for the time being.

Cleaning up the grounds with the tent boys the next morning, Scotty tells Leroy he’s headed home – the Chautauqua shows will go on as scheduled in the town’s high school, so the tent crew won’t be needed. He gives Leroy some bits of melted glass for a souvenir. Clementine’s jewels, it turns out, were fake. Back at the hotel, the sheriff allows Albert to present his case – and a collection is taken up to repay the money Leroy took. Grateful to be alive, Sheamus kicks in fifty dollars. Albert is shamed into leaving the money.

After the junior program for that day is completed, Maggie tells Leroy that her father and Clementine are getting married and – as a family – they are determined that he should come home with them. In an epilogue, we learn that “home” will eventually be Hollywood, where Tremain and Clementine forge jobs as actors, and where Leroy becomes a scene painter. Sadly, the glory days of the Chautauqua are numbered as radio and movies become entertainment staples across North America. In a final scene, we follow Leroy and Maggie, married and with their children, on a trip back to Cutter’s Creek to visit the graveyard where Leroy’s mother is buried and to drive by the weathered farm where he had spent such unhappy days before running away.