To love anything is to be challenged by it. Love shouldn’t hurt you, and at its best, it has the power to push you to your limits in pursuit of growing, changing, and learning something new about yourself. After all, as the late Andrea Gibson once said, “It hurts to become.” 

Depending on what it is you love, that love can also lead you to do goofy and weird bullshit that makes you and everyone around you question your sanity. Think about those who have conquered the 72 oz. Steak Challenge at Sayler’s Steakhouse or Fire on the Mountain’s El Jefe Challenge—those people love steak and wings so much, they have to destroy their bodies, at least temporarily, in service of their love of that thing. Not all of us can house four and a half pounds of steak, some of us have to settle for other forms of oblivion, like seeing nearly 60 bands at a single music festival.

I know first-hand what it’s like to crave that sort of oblivion. Back in 2018, I approached my first solo excursion to Happy Valley’s Pickathon Music Festival with a truly silly goal: To see part and/or all of the 50 different music sets across the weekend. All told, I danced my way to the end of a Shakey Graves performance at Galaxy Barn with a whopping 60 sets under my belt—a feat that made festival founder Zale Schoenborn jokingly ask, “What are you gonna do next year? See every single band?” 

I did exactly that. I set a modest goal of seeing (that is, actually paying attention to) at least 15 minutes of every single band that performed at the 2019 festival. This is possible thanks to one of Pickathon’s best features: Most every band plays two different sets, usually on different days, on different stages.

Was it worth it? Absolutely! Would I suggest doing it? Never—it’s a bonkers thing to attempt, no matter how much you love Pickathon. And yet the urge to do it again can overpower you in ways you never expected. Love dares you to do goofy and weird bullshit sometimes....

So in 2025, after three laid-back years at Pendarvis Farm, I put my six-years-older body through the wringer again out of an unabashed love for the beautiful thing that legions of volunteers, curators, vendors, and bands create in Happy Valley every year. All told, I sampled 74 sets by almost 60 acts—more if you include the guerilla performance by Portland troubadour Johnny Franco at Grove Stage at 3 am on Sunday night.

Do you have what it takes to do this to yourself? Read on for advice and lessons gained by conquering Pickathon yet again—or scare yourself away from ever even considering it!

Ask Yourself, “Why Am I Doing This?”

Yes, it is bonkers seeing every single band at Pickathon—if you’re masochistic enough to treat Pickathon like an eating contest, it’s important to be honest about what’s fueling your goal. Is it because you want to conquer the concept of FOMO? Do you want to up your tastemaker game, introducing your friends to cool new bands? Are you a bit of a try-hard who takes dares from festival curators too seriously? There are no wrong answers to these questions. This year, my fuel was that three years of “taking it easy” at Pickathon meant missing great bands, spending the weekend saying, “Shoot, I missed them!” 

This year was Pickathon’s 25th anniversary, and the world has changed since the inception of the festival. In fact, it’s changed a lot since the pandemic, with the land around Pendarvis Farm now surrounded by cheap housing developments and well-paved streets, an unfortunate juxtaposition to the beautiful bubble we get to exist in once a year. 

Every Pickathon feels like it could be the last one—for such a landmark year, why not pretend it really is the last one and wring every last drop out of it? Why not spend four days trying to be everywhere at once, befriending your fellow campers and falling in love with a dozen bands you’d never heard of?

Be Prepared to Camp!

Of course if you’re going to try and absorb as much Pickathon as possible, you need to give yourself wholly over to the experience. As such, I arrived at the “Welcome Lot” just a few minutes past 9 am on the opening Thursday of the festival, getting my weekend wristband and wandering into the woods to find a campsite. After several years overlooking Woods Stage, I found a place to pitch a tent and hang my wife’s hammock just off the path near Windmill Stage, granting me an easy place to stop by on a shortcut between Windmill and the path leading to Woods. 

Accept, In Advance, That You Will Be Going Into “Rest Debt”

Here’s an easy way to put this into perspective: Over four days at Pickathon, I walked 30 miles across Pendarvis Farm, usually between 10 am and 2 am, though debriefing with excited friends meant never going to sleep that early. This is the aspect of a “Knight’s Tour” that will be non-negotiable for some—if you can’t commit to doing absurd nonsense like getting four hours of sleep before repeatedly hiking from one end of the festival to the other, just so you can catch a few minutes of the three bands performing in the same hour, then this kind of challenge will be nearly impossible for you. And that’s okay, this is NOT normal! 

Pickathon is a Marathon AND a Sprint!

Thursday at the festival is usually a great warmup day, allowing you to get your bearings and lock in with your crew. This year however, there were still 14 bands performing—15 if you count the hour Jake Blount and band put in with Bex Bee for square dancing at Paddock Stage (an outstanding opportunity for people watching). You can knock out a lot of bands just by 100%-ing the first day, and trying as hard as possible to do the same Friday.

Front-loading Pickathon accomplishes an easier second half of the festival, creating pockets of free time as the weekend goes on. Relax, hang with friends, see bands you’ve already seen but loved enough to give undivided attention to. 

Make a Plan—Keep It Loose

This is going to sound counterintuitive, but while it’s important to keep an eye on the schedule and familiarize yourself with which bands play where, you can actually win Pickathon by simply showing up, seeing everyone you can, and making schedule notes as you go along.

Don’t be afraid to switch things up, either—at one point, I rescheduled my date with Rose City Band out at Woods Stage because Jimetta Rose & the Voices of Creation were just too impressive to walk away from. On Sunday night, I abandoned Portugal. The Man to see the last half-hour of New York’s Ben Seretan, who I’d inadvertently befriended over the weekend. 

What's most important is being aware of where your conflicts are taking place. Yes, it’s harder to get out to Woods Stage than it is to get to Galaxy Barn, but the latter fills up quickly—if you can help it, start in the Barn and then head to the forest. Similarly, if one set is taking place in Lucky Barn, ensure at least half-hour to wait in line to get into the intimate, sit-down venue.

Accept That You’re Still Missing Something

It’s possible to see every band at Pickathon, but it’s actually not possible to see everything. I missed out on Cory Hanson scaling the support beams of Galaxy Barn, and Forty Feet Tall singer Guy Moore performing a similar Spider-Man routine at Cherry Hill. On Saturday at 3 am, I missed a mind-blowing party with Reyna Tropical and Motrik at the fabled Pumphouse because it was just too packed. Those moments will always feel like the ones that got away, but if you can pack your weekend with other remarkable moments, the sting of missing out will hopefully pass quickly—even becoming part of the experience. 

Ask Yourself Again: “Why Am I Doing This?”

If you’re anything like me, you do it because of acts like Jimetta Rose, Ben Seretan, SML, and experimental rap duo Revival Season, along with countless other acts I might not have given a second thought to at any other festival, but walked away totally obsessed with because it’s Pickathon. You do the festival for the moments you are present for, moments that etch themselves into your memory, sustaining you amid dark and terrible times (AKA the rest of the year). 

Completing Pickathon is a slog, but it gives anyone willing to try a chance to shake themselves loose of genre expectations, devouring as much of the festival as possible, all to better understand the incredible thing happening at Pendarvia every summer.