Zale Schoenborn didn't set out to make this year's Pickathon the biggest ever. As things have often gone with the annual rock-meets-roots music festival he co-founded 18 years ago, that's just sort of how it worked out.

"It's kind of an accident," says the 46-year-old. "We put those fishing poles in every year. Sometimes it's just chance."

When it launched in 1999 as a fundraiser for KBOO, Pickathon looked even less like a typical music festival than it does now—more like an under-attended wedding reception in the woods. Now, they're eyeing their first potential sellout, with a lineup that includes the just-reunited Wolf Parade, dream-pop masters Beach House, indie-rock vets Yo La Tengo, soft-rock goof-prince Mac DeMarco and Wilco's Jeff Tweedy, who is perhaps the platonic ideal of a Pickathon headliner.

How did the festival get to this point? If we're to continue Schoenborn's fishing analogy, bands (and booking agents) have simply started to take the bait. As the summer festival circuit has continued to bloat and homogenize, Pickathon has come to seem less like a novelty—where acts play in barns and camp alongside fans, where water is free and the food locally sourced—than a respite. As Andrew Savage of Parquet Courts testified, "No advertisers, no waste, just music. This is what all music festivals should be like."

It took a long time to happen, though. So Willamette Week sat down with Schoenborn to map the milestones that have made Pickathon into Portland's biggest little music festival.

1999: Pickathon makes an inauspicious debut at Horning's Hideout, a private park in North Plains, about 40 minutes outside Portland.

A native Kentuckian with a background in festival booking and community radio, Schoenborn started Pickathon to help raise money for KBOO and also pursue, in his words, "the art of the better party." With a lineup mixing various strands of Americana, "headlined" by Portland fixtures Little Sue and Lynn Conover, attendance was sparse.

Schoenborn: "We had probably 90 people, including performers and dogs, at Horning's Hideout. It was just too weird. Nobody who liked any of the music we had would come because they were totally rejecting us for not being pure enough in any one scene. What's the strength of Pickathon now, for the first 10-plus years, maybe 13, was a terrible business curse, because no one got it."

2000-2004: Pickathon continues at the Horning's Hideout location.

Despite the underwhelming start, Schoenborn decided to keep the festival going, more than doubling in attendance in its second year…and then staying there.

"It was fun. It didn't take all year [to book]. It took three months. It was kind of like a basement project, and I didn't have kids. The second year, we got lucky and got to 220 [attendees] or something, because we had Kelly Joe Phelps, which was a high-water mark for the first five years. But we just never had enough momentum where the artists who were big enough were saying, 'Oh, we had a great time, you should come.' That feedback in the system takes a while. It's like growing a tree or something. It's not fast. It's a miracle we survived through those years, because we bounced around in the low 200s."

Kelly Joe Phelps at Pickathon 2006. IMAGE: Tim LaBarge.
Kelly Joe Phelps at Pickathon 2006. IMAGE: Tim LaBarge.

2005: The festival is kicked out of Horning's Hideout at the last minute.

Forced by his neighbors to pick between the three festivals held on his property—the other two being the Northwest String Summit and the annual appearance by jam favorites String Cheese Incident—the owner of Horning's Hideout gave Pickathon the boot with roughly two months to go before the next installment, causing Schoenborn to scramble for a new location.

"I ended up finding this piece of property. Someone we had a connection to hooked us up with a place down in Woodburn, which was next to the Pudding River, which is like a stream that goes through all the farms down there. They had a hay field, and we just decided we could do it there. That's the year we met Mar [Ricketts] from GuildWorks, and he trucked in a bunch of shade cloth. We had to do electricity and water—none of that we had to do before at Horning's. The biggest thing is we never thought about the experience, at all, at Horning's. We did some beer and a little bit of food, but we were cooking food ourselves, and we had one beer. It wasn't about the experience. When we went to Pudding River, that was our first taste."

2006: Pickathon moves to Pendarvis Farm.

Once again, tensions between rural neighbors ("some Hatfield and McCoy stuff," as Schoenborn puts it) pushed the festival to find a new home quickly. Moving to 80-acre Pendarvis Farm in Happy Valley, Pickathon finally put down roots, establishing a close relationship with the farm's owners, Sherry and Scott Pendarvis, and attracting bigger crowds with high-profile bookings such as the Avett Brothers—but not before diffusing their own potential "Hatfield and McCoy" situation.

"The city and neighbors were really unsure of how to handle Pickathon in those early years. The cops would show up thinking they're going to flush out the entire festival. Eventually, we got a five-year conditional-use permit, and we got that from also talking with the neighbors. We had to put up an epic struggle before we talked to them, because they didn't know what Scott and Sherry were up to: They thought it was going to be 50 weekends a year of drug-crazed maniacs running wild in Happy Valley. I met with the whole neighborhood association in that second year, and then I became a little more human. "

2011: Future Islands upend the idea of what kind of music is appropriate for Pickathon.

After settling at Pendarvis Farm, the festival began to chip away at its hippie image, booking artists with cred in both the folk and indie worlds, like Bonnie Prince Billy and Bill Callahan. But by inviting synth-pop act Future Islands, Pickathon moved away from being simply a "roots music festival."

"There were these assumptions about what we would and wouldn't do. [Future Islands] were nothing then; they were absolutely obscure. And people were absolutely pissed off. They either loved it or hated it, nothing in the middle. People said, 'You're going to kill Pickathon.' That was the beginning of a very steep departure of possibilities."

2012: Thee Oh Sees tear up the Galaxy Barn.

The San Francisco garage-rock band's sweaty, frenetic late-night set transformed the cramped barn stage into an unhinged house party, opening the door for future "you should've been there" shows from Ty Segall, Diarrhea Planet and King Tuff.

"That's still one of my top five concerts. I knew we wanted to [book more garage rock] from before that, but no one in that world took us seriously. Ty [Segall] wouldn't come for years, and finally he came. I think [his band] the Muggers were put together for Pickathon so they can all find a way to come [this year]. Think of the band: It's King Tuff, Mikal Cronin, the dudes from Wand and the dude from Cairo Gang. It's all vets of Pickathon."

2013: Pickathon books Feist, its biggest headliner yet.

The Canadian indie-pop singer joined Andrew Bird for what was, up until this year, the heftiest lineup in the festival's history. It didn't come without a price—literally, it forced ticket prices upward, and ultimately inflicted more damage on the organizers' credit cards. But it also helped legitimize Pickathon in the eyes of the national media, attracting the attention of The New York Times, which praised the "sharp and idiosyncratic" booking philosophy and "communal, progressive values."

"That was a big gamble. We went a little bigger than we could handle, and we almost died. We just got crushed by festival economics. But everything gets easier where we're at now. It's the golden age. It took forever to get here. Let's try to keep it in that sweet spot."

SEE IT: Pickathon is at Pendarvis Farm, 16581 SE Hagen Road, Happy Valley, Thursday-Sunday, Aug. 4-7. Weekend tickets are $290. See pickathon.com for a complete schedule.