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The challenges and adventures of life on the road, as told by 14 bands

I asked a bunch of musical artists about touring life. They gave me an earful.

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The Pickathon main stage, in all its glory.
(Photo: Jason Redmond)

Earlier this summer, I attended the Pickathon music festival in Happy Valley, Oregon, just outside of Portland, with a simple mission: to talk to as many bands as possible about life on the road.

The festival, which just celebrated its 19th year, is a favorite among musicians for its friendly vibe and lack of commercialism. Relative to most big-name music festivals, it is a calm, civilized, music-focused event — a festival made by people who like festivals, rather than people who want to maximize returns. It’s rare to see a band perform without offering at least a few words of breathless appreciation for the festival itself. Some bands (including indie icon Ty Segall) travel to Portland every year just to play it.

Fans camp in the woods of Pendarvis farm (a lovely bit of Oregon backwoods that hosts only this one event during the year) and enjoy music on six different stages, ranging in size from a large outdoor venue to a small, hot, sweaty barn. Every band that’s invited plays at least twice, so it is possible to see every act, and the ratio of people-to-land is about a fifth of, say, Coachella’s, so there are never unwieldy crowds.

lucy dacus on the woods stage
Lucy Dacus performing on Pickathon’s gorgeous Woods Stage.
(Photo: Jason Redmond)

All food and beverages are served in reusable bamboo bowls or stainless steel cups, so there is virtually no trash anywhere. (I wrote a long profile a few years back about Pickathon’s environmental innovations.) And it is aggressively family-friendly, with separate shows, activities, and classes for children.

It doesn’t generate much profit. When I ran into co-founder Zale Schoenborn, I asked how they make money without big corporate sponsorships or jam-packed crowds. He smiled and raised his hands. “You can either have a business model,” he said, gesturing in a grand arc, “or this.”

And the music! Though Pickathon started (as the name would indicate) with bluegrass and Americana, it has since branched out to rock, funk, soul, and hip-hop. Where most festivals focus on getting as many chart-toppers as possible, Pickathon focuses on bands that are on the verge of breaking through, or old pros known mostly to devotees. It is always a goldmine of new music.

Sweet Spirit, playing in Pickathon’s Galaxy Barn.
Sweet Spirit, playing in Pickathon’s Galaxy Barn.
(Photo: Teyo Tyree)

This year, I tried a bit of a journalistic experiment. Rather than focus on a particular band, I asked as many artists as possible the same two questions. 1) What is your primary challenge as a musical artist right now? 2) What is the most intense experience you’ve had on the road in the last few years?

In all, I talked to more than 20 bands and artists, catching them before shows, after shows, sometimes lounging backstage with a bamboo bowl full of vegetarian food. I’ve whittled down a selection of those interviews below.

Some of the names you might recognize; many you won’t. All are working artists, touring and playing music for a living. Here’s what they had to say.

Y La Bamba

Since 2008, Luz Elena Mendoza has been playing eclectic folk pop under the name Y La Bamba. Her fourth album, Ojos Del Sol, was released in 2016.

What is your primary challenge as a musical artist right now?

My biggest challenge is getting over that fear, feeling intimidated by society's pressure of who I should be as a person. Being a female, sensitive, or just empathetic is really hard in the music industry. Being an artist. That's the challenge.

I've been aloof to a lot of the industry stuff, just because I’ve been in my own world. This has been the first year that I've felt a lot of pain and grief from being just a little bit more aware of it.

What is the most intense experience you’ve had on the road in the last few years?

Joseph Gordon Levitt came to one of my shows out in Santa Monica, on the pier. This was like six years ago, I think Batman or Spider-Man or whatever movie he was in just came out. We play the show and I just want to go roll a joint after, but everybody's like, no, no, somebody wants to talk to you. It was a couple. And the girl started talking, “Oh my god, I love your music, I have your record, it was our first song that we kissed to.” And dudebro was wearing, like, a hungry badger hat and sunglasses.

And I was all, thanks! And there was a pause. I'm like, “Has anyone ever told you ... you kinda look like Joseph Gordon Levitt?” He doesn't say anything. No one says anything. And then the conversation goes on, and I shoot the shit again. Then he laughed again, and his dimples ... and I was like, “No, really, has anyone ever told you ...” My friend Isaac, in the background, was finally like, Luz, it's him!

It was really funny. And then he smoked us out in our van!

Courtney Marie Andrews

Courtney Marie Andrews has been performing since she was 15, as a session or touring musician with dozens of artists and on six of her own albums. Her latest release, Honest Life, came out last year.

What is your primary challenge as a musical artist right now?

To write a million good songs — not just good, but great. Quantity and quality is what I'm going for. It's a lot of personal pressure, but I'm willing to put it on myself.

What is the most intense experience you’ve had on the road in the last few years?

We had a booking agent at the very beginning of my first tour who booked us some strange places. One of them was this place called Landers, California, right outside of Joshua Tree.

We drove down this dirt desert road for 15 miles. It was a bar in the middle of nowhere. People say “middle of nowhere,” but there's, like, a gas station. This was the middle of nowhere.

There were like five people at the show, maybe 10, and everybody was dressed like Mad Max characters. The owner was all, hey, don't worry, I got a security guard for you guys. And we're like, why do we need a security guard? And he's like, if anybody gives you trouble, just holler over to Al. Al walks up and he has, I kid you not, a tear-drop tattoo.

Then there was the guy dressed in an Elvis suit who lived in a pit behind the brewing company where we were playing. You know Parks and Recreation? Chris Pratt lives in a pit? This guy did too! But in Landers.

The worst part about it is, he tried to ask us, do you wanna stay at my place? We're all like, yeah, maybe. We thought he had a little house or something. Turns out, he was offering the pit!

Deer Tick

Centered on the songwriting of John McCauley, Deer Tick has been playing with various lineups since 2004, building up an enormous underground fan base. On September 15, they will release two albums, the mostly acoustic Deer Tick Vol. 1 and the bluesy, rocking Deer Tick Vol. 2.

What is your primary challenge as a musical artist right now?

Ian O'Neil (guitar, vocals): Getting a consistent stage sound throughout the festival season. That's our biggest challenge right now.

John McCauley (guitar, vocals): If we look like we're having a bad time, we probably are.

What is the most intense experience you’ve had on the road in the last few years?

Dennis Ryan (drums): That time we had three connecting flights?

McCauley: We haven't toured much lately.


Justin Osborne has been recording and releasing music since he was 15. In 2014, he formed Susto, whose country-flavored space rock was an immediate hit. This year they released their second album, & I’m Fine Today.

What is your primary challenge as a musical artist right now?

Trying to get huge. Trying to get the shows bigger. I'm a bit obsessed with seeing how far we can go with it.

You have to be killing it in everything. You have to have a really excited and reputable label behind you, to help get the PR going. What you're creating has to be relevant — it has to speak for and to people right now. And the other thing is, now it's so hard to ever leave the road. The recording doesn't get to happen, and when it does it's kinda rushed. You're trying to be everywhere at once, you're preaching the gospel, but at the same time you have to keep up the writing.

What is the most intense experience you’ve had on the road in the last few years?

I went skydiving on acid in Chicago. It was terrible.

We stayed with this guy who was a little crazy -- if that makes it [into the story], Jason, I love you — and we stayed up all night partying after we played this bar. We woke up the next morning and he was like, “You guys wanna jump off a fucking airplane today?”

I mean, I can't say no. And we had just gotten this really good LSD. I think it might have actually helped.

I realized up there how terrified of heights I really am. I had kinda felt it before, when I'd gone mountain climbing and stuff, but ... jumping out of an airplane is the most miserable thing I've ever done in my life. My parachute didn't even deploy the first time. They had to pull the secondary chute and it jerked really hard and my back was fucked up the rest of the tour. But I'm all right now.

Tank and the Bangas

The winners of NPR’s 2017 Tiny Desk Concert contest, New Orleans-based Tank and the Bangas are ... difficult to describe: a captivating mix of rap, singing, avant garde funk and rock, and a splash of Disney. Their debut album, ThinkTank, came out in 2013. In 2017, they’ve released only one single, Quick. Hopefully an album is on the way.

What is your primary challenge as a musical artist right now?

Tarriona "Tank" Ball: Just being a disciplined person in everything — in eating correctly, exercising, vocally rehearsing, resting, just discipline. It is hard on the road.

What is the most intense experience you’ve had on the road in the last few years?

We planned to go live in London for three months, and we tried to stay with a guy, but he never showed up. We ended up staying in the outskirts, in a camp, in a cottage, where we slept with instruments all over our faces and on the floors in the kitchen, for about five weeks. We bought a Japanese van and it broke on us every week. That was hard as well. Baby did we rough it!

But it was also amazing. We're going back next week.

Sweet Spirit

Based in Austin, Texas, Sweet Spirit plays a kind of sweaty, swaggering rock that is too rare these days. With touches of funk and doo-wop, boy-girl harmonies, a Queen-like sense of theater, and the occasional face-melting rock jam, they were the best live act I saw at Pickathon this year. Their second album, St. Mojo, was released in April.

What is your primary challenge as a musical artist right now?

Joshua Merry (guitar): Rent. If I'm being 100 percent honest, money.

I broke my guitar last night, so I have to get a new guitar. I fucked up something on my pedal board and it was really frustrating. And I drank loads of beer. I have an SG, which is the thinnest and most breakable of guitars, and at the end, I threw it at the stage and I guess it broke. It’ll be about $1,000 to replace.

We all make money doing this and we all have jobs when we go home. I wait tables in Austin, Texas. I'm in three bands, so I basically go on tour and come back and work as much as I can and then go back out on tour.

What is the most intense experience you’ve had on the road in the last few years?

Probably South By [Southwest]. Last year we were playing the first day, headlining this place called Hotel Vegas, which is one of the best places to play in Austin. Our drummer Danny got food poisoning. [The club owners] were like, don't you know anyone else who plays drums? And I’ve been playing drums since I was three. So eventually it was decided that I was gonna play drums. In front of 1,000 people.

We have kind of a reputation around Austin for burning shit down, so everyone was like, should we have our first bad show in front of 1,000 people? I was super nervous.

But we killed. It was fucking awesome. So I just got, like, time-travel drunk.

Mandolin Orange

Andrew Marlin and Emily Frantz have been releasing albums as Mandolin Orange since 2010, steadily building a following devoted to their quiet Americana, with timeless melodies and intricate harmonies. Their latest album, Blindfaller, was released last year.

What is your primary challenge as a musical artist right now?

Emily Frantz (fiddle, guitar, vocals): Doing all the festivals in the summer. You miss out on a lot of the jam-and-get-comfortable time you have when you're playing clubs and on tour. You throw and go, throw and go, which is fine, but having months of that, with no time for everybody to just play together and work out new stuff, casually — here at the end of the summer, that's something we're feeling.

What is the most intense experience you’ve had on the road in the last few years?

Frantz: Just two weekends ago, we played a big hometown show in North Carolina. It was by far the biggest headlining show we've ever played, one of the biggest crowds we've ever played to, so it was super exhilarating, but also very overstimulating. Playing at home is amazing and the crowd is so supportive, but it can also be really distracting, because everyone you've ever known is there.

Andrew Marlin (mandolin, guitar, vocals): We're such a quiet band that sometimes, that space between the volume you're playing at and the volume you feel like you should be playing at — there's a lot of intensity in that space. Especially at a show like that, where you feel like you need to get up there and be really loud, be really intense, be in people's faces. But that's just not what we do. So that was intense for me, just trusting the audience and trusting our tunes and trusting ourselves.


Pinegrove is a Montclair, New Jersey, band that plays country-tinged indie rock, at turns introspective and soaring. Earlier this year they released a compilation of live recordings, Elsewhere, that they are giving away for free or a donation to the Southern Poverty Law Center.

What is your primary challenge as a musical artist right now?

Evan Stephens Hall (lead vocals, guitar): I've been thinking about vulnerability a lot — how to perform that authentically. Performing, of course, is artificial, but how can you do it energetically, and like you mean it? My friend Zack Burba [of Seattle’s IJI] suggests that it's like being yourself, but with an exclamation point.

What is the most intense experience you’ve had on the road in the last few years?

More than anything it's the accumulation. It's all intense. It's either intense solitude or intense community. You hardly ever get a break. It’s also the physicality of geographical displacement. Our bodies are really not made to be traveling constantly. It feels disruptive to do that, in a biological way. It's a challenge and it's intense, but we also love what we do.

Dori Freeeman

From Galax, Virginia, Dori Freeman plays an old-fashioned sort of country-tinged pop, with hints of Patsy Cline and Loretta Lynn. Her debut album was released early last year; her next is due in October.

What is your primary challenge as a musical artist right now?

General stage fright. I just really don't like being on stage. I know it's weird. It's getting better, but there's always a few minutes or a few songs within every set that I'm really nervous. Weirdly, looking at people kinda helps. I used to just look over heads, but now I feel like making a little bit of eye contact helps in a weird way.

What is the most intense experience you’ve had on the road in the last few years?

We played in Australia in March and there was one particular multiple-artist workshop we were supposed to do. It was early in the morning. I won't say who it was with, but two of the other artists were very drunk. There ended up being some confrontation about me being American and Donald Trump.

They weren't Australian, they were Irish, but the Australian audience was kinda in on it too. Everybody was like, “Oh, the American, let's go after the American.” So I just pulled my cable out of the guitar and walked off and didn't do the workshop. It felt a little bullying, so I didn't want to participate. That's the most intense thing that happened to me.

Hiss Golden Messenger

Longtime festival favorites, Hiss Golden Messenger is the brainchild of MC Taylor, who has been releasing folk-rock albums under the name since 2008. His new album, Hallelujah Anyhow, comes out on September 22.

What is your primary challenge as a musical artist right now?

MC Taylor: Keeping the hope and faith alive, that I can keep the thing I love to do pure. You can get it tangled up really quickly. A lot of my peers and contemporaries have fallen by the wayside over the years — people that have died, or just been, like, fuck it, I'm gonna get a job. For a band like Hiss Golden Messenger, we sort of attract fans one by one. We've never had that overnight moment, which is maybe good, but that long journey requires some stamina.

What is the most intense experience you’ve had on the road in the last few years?

We've been out on the road a ton, so it's a little bit of a blur. This summer has been intense because it's festival season, which means we're traveling with a skeleton crew, at a different place every weekend. When my wife and I were planning what the summer was gonna look and feel like — I have two little kids — I was saying, “I'm only gonna be gone on the weekends and I'm gonna have all week long to be around!” But it hasn't really felt that way.

Lucy Dacus

Lucy Dacus makes wry, confessional, confrontational indie rock in the mode of Liz Phair. Her debut album No Burden, released last year, garnered gushing praise from the indie music press and, improbably, one-time democratic VP candidate Tim Kaine. She recently finished recording her follow-up; it will be out in early 2018.

What is your primary challenge as a musical artist right now?

Finding alone time. When you're on the road, you're in a van for most of the day, and then you get to the venue and you have to actively be checking sound or making sure everything's in order, and then you go to sleep, and wake up, and drive again. You're with the same group of people. I love who I work with, but yeah, it seems basically impossible to find any substantial alone time.

What is the most intense experience you’ve had on the road in the last few years?

Two days before we were going to leave for the five-week tour we're on right now, our van broke. Just wouldn’t run. We ended up finding a van the next day and buying it the night before leaving.

Billy Strings

Billy Strings is William Apostol, a shaggy, good-natured Michigan native (now based in Nashville) who has taken the traditional music scene by storm. His live shows feature high-energy guitar picking so technically adept as to verge on the supernatural — but fun, too. His debut album, Turmoil & Tinfoil, is due out September 22.

What is your primary challenge as a musical artist right now?

Keeping all my shit together. You know? Being out on the road all the time, maintaining a relationship with my girlfriend a thousand miles away.

But that's the only thing that's ever a struggle at all. I love being on the road.

What is the most intense experience you’ve had on the road in the last few years?

I was robbed while I was asleep in the van, north of Indianapolis. We had a little mattress in there — it was a trio at the time, so two people could sleep in the hotel room and one person could sleep out in the van.

I woke up in the middle of the night to take a piss, got back in, shut the door, and went to sleep. And I didn't lock the door. Then somebody came in. I figured it was Don Julin, the fellow I was traveling around with, getting in there to roll a joint or something, cause the dome light turned on, and I woke up and said, "Man, turn that light off," and fell back asleep. Then I woke up and the rain was pouring in the door, left wide open. I go, "Hello?" and there was nobody there. So I shut the door, and I'm looking around the dark parking lot, like, somebody was just in the van.

They took the GPS. We shoulda took it down off the dash.

Luke Bell

Wyoming’s Luke Bell plays old-fashioned country music with touches of honky tonk and swing. His eponymous third album was released last year.

What is your primary challenge as a musical artist right now?

Luke Bell (guitar, vocals): Drinking enough water.

Matt Kinman (fiddle, vocals): You wanna know the truth? Dealing with modern people and the way they do things now. I don't like it. I've been playing music for 30 years and the way they do things right now is ass-backwards.

Years ago, when I was playing professionally all over the country — and I played with a lot of big names — first off, the promoter or the man that was wantin' you to play with 'em would call you on the phone and talk to you directly. Now, the person theirself don't even contact you, it's through somebody else that sends an email and a text! I don't appreciate it. And I don't like it.

And you get paid less. I'm makin' less money than I was 30 years ago. And we get treated less. It's the truth.

What is the most intense experience you’ve had on the road in the last few years?

Bell: I got lost one time and had a gun pointed at my face, in Missoula, Montana. Last summer, we played some shows with Hayes Carll and I got ... well, I was wandering around, trying to find a place to sleep, and I accidentally opened the wrong door. He was standing in that doorway with a gun.

Anna & Elizabeth

In what is partly a musical act, partly an art project, Anna Roberts-Gevalt and Elizabeth LaPrelle track down old field recordings of traditional music, taking unknown and forgotten songs and rerecording them for contemporary audiences. Their third album is due in 2018.

What is your primary challenge as a musical artist right now?

Anna Roberts-Gevalt: Being overwhelmed by choice. We have access to so much music and so many ways of performing and being. I like this drone fiddler, and this complicated jazz composer, and Laurie Anderson, and this old man playing banjo, and the new Beyoncé record. It's a lot to synthesize. That can be hard when you're sitting down to make something.

What is the most intense experience you’ve had on the road in the last few years?

Roberts-Gevalt: We did a show in Vermont where I got to introduce the great-niece of this woman who went around and made 4,000 field recordings. She's carrying on her ancestor's work. I introduced her to the great-granddaughter of one of the women recorded, and then we all sang a song as part of our show. You realize, "Oh, these songs are really old and they've been carried by a ton of people." We're just one link in the chain.

Elizabeth LaPrelle: It felt as though spirits were in the room and things were coming full circle.

Bonus third question!

With several of the artists I spoke with, I snuck in a third question, some variant of: What is your bad habit/guilty pleasure/food indulgence on the road? Here, just for fun, is a selection of their responses.

John McCauley of Deer Tick: I bring my X-Box with me, or my PS4.

Anna Roberts-Gevalt of Anna & Elizabeth: I definitely spend a ton of money on museums.

Billy Strings: Those little packaged donuts that you get at the gas station.

Courtney Marie Andrews: I love fried chicken, especially when I'm in the South. I always regret it, but man it's so good.

Dori Freeman: Auntie Anne's, the pretzel place.

Evan Stephens Hall of Pinegrove: Straight up? It's alcohol.

Lucy Dacus: I love canned fish. Straight out of the can.

Your author, after interview 17 or so.
Your author, after interview 17 or so.
(Photo: Teyo Tyree)

Luz Elena Mendoza of Y La Bamba: Drinking.

Emily Frantz of Mandolin Orange: The constant gas station stops require a lot of self-control. It's really gummy bears.

MC Taylor of Hiss Golden Messenger: When I'm on the road, I'm probably on my phone a little too much. There's a lot of hours in the day to kill.

Justin Osborne of Susto: I'm a sucker for a Denny's build-your-own slam — hashbrowns, two eggs sunny, they have this sweet sausage and it's only two pieces so you don't feel too bad, and then a side of fruit and unsweetened ice tea.

Josh Merry of Sweet Spirit: There's all of these tropes and lore from bands of the Green Day era of, you just eat shitty, you eat fucking Taco Bell all the time. That's why the album's called Dookie. But we eat better — you have to, because every day you're exerting yourself super-hard, not resting, and then drinking so much. You have to fucking have discipline.

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