In 1999, a Kentuckian named Zale Schoenborn organized a fundraiser for Portland’s KBOO community radio station. He booked Horning’s Hideout, a private park in North Plains, and assembled a varied lineup of Americana acts. He called it Pickathon, and about 90 people showed up.

Flash forward a couple decades, and Pickathon is now among the country’s most beloved festivals, drawing 10,000 annually to Happy Valley’s Pendarvis Farm for a music-filled campout in the woods. Not content to be confined to a few days in August, this year Pickathon opened a year-round venue in Portland called the Showdown, which books country-ish acts and hosts regular square dances on SE Powell Boulevard, just around the corner from the Aladdin Theater. And a couple weeks ago, the festival announced the launch of a nonprofit, Pickathon Creative Neighborhoods, geared toward year-round mentorship in the trades and other creative fields: think job training programs for aspiring baristas, film camp at Benson High School, and teens mentored by muralists.

Pickathon, in other words, has become bigger than Pickathon. But a quarter century on, its heart remains the festival. This year’s installment, taking place August 1–4, welcomes back a handful of returning acts, including headliners Courtney Barnett, the wry and virtuosic rock star who first played Pickathon in 2011 (several years before she got big), and prolific oddball Bonnie “Prince” Billy, who played in 2010. But Pickathon is a festival that prides itself on discovery, and that remains true in 2024. Another headliner this year is Durand Jones, a Louisiana-raised artist who recently struck out solo; his soul-and-gospel sound evokes Leon Bridges, a 2015 Pickathon alum.

This year’s lineup also hews particularly youthful, with half the musicians 25 or younger. A Brooklyn band called Geese is among the Gen Zers that Schoenborn, now Pickathon’s CEO, is most excited for. Members graduated high school together in 2020, and Schoenborn saw them play Portland’s Polaris Hall last fall. “Probably the next great American rock band,” he says, with a frontman “totally channeling Mick Jagger, but his own version of it.”

That finger-on-the-pulse booking sensibility is one of Pickathon’s calling cards, and there’s a long list of artists who’ve shot to fame shortly after a Pendarvis Farm appearance: Barnett and Bridges, of course, but also Future Islands, Lake Street Dive, Angel Olsen, Margo Price, Big Thief…the list goes on. This year, Schoenborn also has his eye on British folk singer Billie Marten, cumbia-inspired instrumental trio LA LOM, and Pahua, a genre-bending and danceable percussionist, composer, and DJ from Mexico City. As is Pickathon practice, most artists will perform twice, at two of the fest’s seven stages.

And it appears Pickathon’s talent spotting will continue for at least another decade: last winter, the fest secured a 10-year conditional use permit to remain at Pendarvis Farm. The campaign for approval attracted more than 1,500 letters of support and culminated in a packed hearing at Happy Valley City Hall. “People told stories about how the festival had changed their lives, or their kids’ lives,” Schoenborn says. “It was incredibly humbling to go through that.”

2024 also continues a rebuild that began in 2022. When the festival returned following a two-year pandemic pause, it redesigned its layout to create so-called neighborhoods across the farm. Each neighborhood had its own focus and vibe, not to mention its own bars, food carts, and/or interactive art. It was a major reset, Schoenborn says, and the last couple years had their kinks: a bit of a parking fiasco in 2022, bumpy gear delivery to campsites in 2023. But he sees Pickathon hitting its stride this year. That means smoother operations, yes, but also more architecturally elaborate stages, wilder art installations, a bounty of kids’ activities, and a dizzying array of additional programming, from comedy shows to author readings to foot massages to a series of multicourse meals partnering chefs with musicians.

“We’re in that sweet spot,” Schoenborn says, “where the vision really comes to life.”

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Visit Pickathon’s website for the full lineup and ticket info.