For once, an interviewer had stumped Orson Welles. In a hotel room in 1960, a seemingly innocuous question from a television reporter about a sense of home has him searching his pockets for a matchbook. He pauses, eyes downcast, his brow dented in thought. “I suppose it’s Woodstock, Illinois, if it’s anywhere,” he replies. “I went to school there for four years. If I try to think of a home, it’s that.”

Throughout the month, Welles’s homeland has repaid the compliment. On May 8, Woodstock Celebrates, the cultural stewards of this town of 25,000 located 50 miles northwest of Chicago, launched a three-week festival to hail the roving master as a product of the prairies. Of all the centennial celebrations of Welles worldwide, this is perhaps the most territorial, the most intimate.

The weekend kicked off with a screening of Magician: The Astonishing Life and Work of Orson Welles at the historic Woodstock Opera House, where Welles made his professional directorial debut at age 19. Before the show, director Chuck Workman stood at the podium on Welles’s namesake stage, the christening of which is captured in the film. He explained that, before researching Welles’s life in Woodstock, he “didn’t know how much this area was the cradle of arts in those days. I knew Frank Lloyd Wright and Orson were around, but I didn’t know how much going on in Chicago would spread out hundreds of miles from Chicago to make an art world.”

Welles at 18

Orson Welles at 18

After graduating from the progressive Todd School for Boys in Woodstock in 1931 and sidestepping college, Welles famously decamped for Ireland and secured work onstage. Three years later, he returned to Woodstock to host a summer season “in the European spirit and tradition” at the Opera House, convincing his Dublin counterparts (actors and production mavens Micheál Mac Liammóir and Hilton Edwards) to join him, a coup covered in the New York and Chicago press.

It was during this summer in Woodstock that Welles worked on one of his first short films, the amateurish riff on surrealism, The Hearts of Age. More importantly, this was the moment when Welles proved himself as a master of publicity­ with a strategy he dubbed “The Selling of Woodstock, Summer of ’34.” The promotional materials he doled out coaxed lines of limousines to the town he’d trumpeted as “the grand capital of Victorianism in the Mid-West” and “a wax flower under a bell of glass.” (There is some contention that these words were ghostwritten by Thornton Wilder.)

The productions became mandatory viewing for leading Chicago theater critics. As Simon Callow notes in Orson Welles: The Road to Xanadu, even the flagship Marshall Field's department store on State Street ran full-page ads for the latest gowns to flaunt at Woodstock galas. It was all the more impressive given Welles’s saturation of the local media. Even at age 13, for example, he was anointed drama critic of the Highland Park News, published in the affluent North Shore suburb, where he regularly savaged local productions in his column.

Hearts of Age

The Hearts of Age

In his introduction to the screening of Magician at the Opera House, film scholar Michael Dawson likened Welles to a “broken water main” of talent, an apt metaphor on a particularly stormy night. After the screening, attendees were encouraged to brave the rain and walk to the nearby courthouse to skim Welles memorabilia and sip wine provided, from afar, by Francis Ford Coppola. Outside the opera house, festivalgoers moved in single file beneath the network of canopies lining local shops, including an independent bookstore that offered Rosebud and Macbeth cookies for sale.

The town square, cherished by locals for its star turn in Groundhog Day, where it doubled as the Punxsutawney of the mind for its North Shore-raised star, Bill Murray, remains virtually unchanged, save for the no-handgun placards dotting the garbage cans at the entrances. As attendees dodged Ned Ryerson’s doozy puddles and headed toward the whirling spotlights in a pickup truck parked at the courthouse steps, a man behind me, laughing along with his friends cracking Gene Kelly jokes, seemed to best capture the spirit of the place. “Actually,” he said, “the spotlights work better when there’s rain.”

The charismatic headmaster at the Todd School during Welles’s attendance was Roger Hill. “Headmasters are big frogs in small puddles,” he once said. “They constantly speak down ex cathedra.” Hill favored a free-range, self-empowering approach to education. Students could chase their muse on the stage, at the printing press, even in the school dog kennel. Welles swallowed the curriculum whole, save for geometry and all sports but fencing, which he felt bolstered his stage presence. Upon his arrival at Todd, Welles said he “fell in love” with Hill.

“I tried to find a way to capture the attention of this fascinating man who fascinates me tonight as much as he did the first day I laid eyes on him,” Welles remarked on a 1970 episode of An Evening with Orson Welles. “He has never ceased to be my idea of who I would like to be.”

The Stranger

The Stranger

Welles’s tributes to Hill and the Todd School were often more subdued, as James Naremore illustrated in a Saturday afternoon lecture on Welles’s Nazi-hunting thriller The Stranger. The setting for the talk was the Rosebud Theatre, a makeshift events space in Woodstock’s local VFW hall, on the outskirts of the same town square that inspired the film’s backdrop. While Welles’s masquerading prep-school teacher is a far cry from Roger Hill, the Harper School where he hides from a war-crime investigator played by Edward G. Robinson—a role, Naremore noted, that Welles originally intended for Agnes Moorehead—bares striking resemblances to Todd.

Welles’s preferred location of Woodstock was scrapped by the studio, along with “powerfully grotesque, impressionistic dream sequences” and Latin American scenes that Welles valued over the more traditional fare that remained. But Naremore pinpointed various Todd references in the film—teachers’ names, school proverbs—that Welles smuggled in, particularly on signage and in his own handwriting, a minor production detail for which he had maximum control. (Coincidentally, Woodstock was the longtime home of Chester Gould, who drew the Dick Tracy strip from his rural studio and maintained an office in the square, where his brother Ray lettered the comics. In interviews for This Is Orson Welles with Peter Bogdanovich, Welles mentions that Gould had a “great sense of set-ups, real good movie set-ups.”)

While examples of Welles’s hidden hand underscored Naremore’s presentation, a discussion later that evening with the weekend headliner, Oja Kodar, examined Welles as a man in full. Making a rare stateside trip from her home in Croatia, Welles’s partner and collaborator from the early 1960s until his passing held court before a rapt ballroom audience. Flanked by banners with photographs of Welles in his moon-faced youth—uniform rumpled, hair center-split—Kodar brought a certain majestic air to the proceedings.

The Other Side of the Wind-era

John Huston, Orson Welles, and Peter Bogdanovich

At the midpoint of her discussion, she yielded a portion of her time to Roger Hill’s grandson, Todd Tarbox, who was in attendance. Tarbox spoke of the Hill family’s enduring respect for Welles, as well as the long-held lament that Welles didn’t maintain more friendships from his youth. The disconnect was probably not out of hostility: in Road to Xanadu, Callow quotes a letter from Maurice Bernstein, Welles’s legal guardian after his father’s death in 1930, stating that Welles looked up to the other children at Todd, but that they “mystified him, even scared him.”

The evening’s moderator, critic Jonathan Rosenbaum, stressed Kodar’s importance to Welles’s literary legacy, tracing the lineage of several Welles films, completed or otherwise, to Kodar’s original short stories. “I’m not going to be like one of those people who get an Oscar and then starts thanking their grandmother, all the way up to Adam and Eve,” Kodar said, self-effacingly. Yet for over an hour, she shared inspirations for her prose: fascinating scenarios of mistaken identity, exposed voyeurs, lost souls.

While remaining short on details about the release of The Other Side of the Wind, Kodar offered insights into her mystifying title for the still-unfinished film. In the early 1960s, she and Welles were drifting through a studio back lot in Rome. “The day was very windy,” she said, recalling that Orson looked like “a giant bat” as his black cape flapped in the wind.

Orson Welles

Orson Welles

“When people ask me about Orson,” Kodar continued, “I still think today of him as an element of nature. In a certain sense, he was more than human. He was wind. I know, of course, he was human and he had a mother and father and a brother, but when I looked at him that day [in Rome], I was thinking, ‘He’s the wind. Does the wind have a brother? What is the other side of wind? It’s something else.’ This is how I came up with this title. Orson loved it, and he said it fit the character of Jake Hannaford, played by John Huston.”

She later likened Huston to an “unfrocked priest.” The way he listened, she explained, impelled you to confess.

“Living with Orson, you don’t know where you live,” Kodar said as the conversation drew to a close. “I didn’t live in Hollywood. I lived on the moon. I lived in the water, the air. There was no geography.”

For one night, the landscape that shaped Welles was underfoot.