The 2026 Lineup: Where Legends Play the Woods and The Future is Born
After 26 years of elevating emerging artists like Geese, Billy Strings and Leon Bridges, the Portland-area festival returns with a lineup that balances discovery with icons including Steve Earle, Shakey Graves and Marcos Valle.
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Pickathon Blog
Laughs in the Lucky Barn: Comedy Showcase Lineup

Pickathon’s late-night comedy club is back. For her tenth year, Amy Miller hosts Laughs in the Lucky Barn — a stacked 2026 lineup headlined by rising Tonight Show star Laura Peek, plus Portland favorites Shain Brendan, Julia Corral, and Sean Jordan. Ninety minutes of the funniest people working today.

Inside Pickathon's 2026 Curation Series

Pickathon’s most intimate tradition returns for 2026: five gatherings pairing chefs and performing artists in unexpected combinations, each limited to just 100 guests. From Cafe Olli and The Brothers Comatose to Screen Door and The Travelin’ McCourys, here’s the full lineup.

Wednesday Hootenanny: Early Entry Kicks Off with a Barn Dance

This year, Early Entry lands on Wednesday. Gates open to the public at 5PM on Wednesday, July 29, giving you a full evening to settle in before the music begins Thursday.

From Sea to Stage: Cherry Hill Surfaces With a Net-Woven World for 2026

Woven from disused fishing nets by the PSU School of Architecture, Cherry Hill’s 2026 stage translates ocean waves into musical waves before shipping on to Ukraine to save lives.

Lucky Neighborhood 2026: Welcome to Kaleidoscope City

Modular structures that grow like living cells, 100% re-use, and a second life as an outdoor classroom. Step inside Kaleidoscope City, the Lucky Neighborhood’s 2026 transformation.

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