Around 2000, Gregory Alan Isakov spent a year living in Trumansburg while taking horticulture classes through the Cornell Cooperative Extension. The singer-songwriter never imagined back then that he’d be playing music for a living. Almost two decades later, he has recorded several albums that have won much critical applause along with an intensely devoted base of listeners. 

On his latest album, “Evening Machines” (2018), “San Luis” evokes the chimera that is California, impossibly beautiful but just out of reach. “Wings in All Black,” the closing song, suggests the campfire but is touched with Isakovian melancholy.


JW: Tell me about your time in this area. 

Isakov: I lived with my friend, who had a place right in the center of Trumansburg. That was such a great town. I was taking some horticulture classes, on wild plants and herbology. I remember doing plant walks through the gorges, all those waterfalls. 

While I was here, I was playing a lot of music, but I never thought I was going to do it for a job. I was definitely on the plant track. I would play mostly in my kitchen but at coffee shops sometimes. 

JW: So when did you realize that you could make music your job?

Isakov: I was working on a farm in Lyons, Colorado, which is kind of like what Trumansburg is to Ithaca, even to the point that Lyons has a lot of bluegrass. It feels like you’re going back in time twenty years or something [laughing]. I was doing a landscaping job, a flagstone job on a big walkway, and I booked a show up in Breckenridge playing a bar for three hours. I probably had forty-five minutes of original songs, so I played a lot of covers too. The place said they’d pay me a couple hundred bucks, with dinner. And I thought, No way, that’s like a day-and-a-half of flagstone. Insane. Until then, I never thought music would be a viable option. 

I was 27 when I made the jump. I left the farm where I was living, and my relationship at the time ended. I was living in my car for the next few years, and I thought, alright, let’s not even have a backup plan here, let’s just see if this works. 

JW: And you were able to support yourself? 

Isakov: Yeah, minimally. A lot of it was just, can I get to the next town? Or can I get to the next campsite? And it was a lot of tours through Montana and Washington. I’d make records at Kinko’s on the way and try to sell, maybe, ten of them so I could pay for gas and the campsite. Since I was on my own, during these three-hour gigs, I started varying my approaches, like using a different microphone for my harmonica to break up the sound. And along the way, I developed a lot more material. 

JW: Your music is filled with a wanderer’s ethos. What do you live for now as a traveler?

Isakov: I have a writing regimen early in the morning. On tour, our group has about eleven people, and I’m such a hermit. I always try to find somewhere I’ve never seen and try to write a little bit—enough writing to fill out a couple of postcards. And I usually like to shoot photos too.

Being in a bus has also changed things. When we started touring in a bus, all of a sudden we weren’t sitting in a van all day trying to get to the next place. That is the coolest thing. You can actually just wake up and you’re somewhere. And you have all day to check it out. That was a luxury that I never thought about beforehand. 

JW: Tell me about your songwriting process. For example, how does a song like “All Shades of Blue” [from the 2013 release The Weatherman] happen?

Isakov: Co-writing is not something I do very much, but for “All Shades of Blue,” I was fishing with my great friend from Austin, Johann Wagner. We’ve written a few songs together. Usually it’s such a solitary thing. But it’s fun to hang out friends who are as nerdy as you are and who love words as much as you. As we were fishing, we saw these giant flies, and we were swapping off song lines. You know, “When the wine stops workin’.” We were sitting outside fishing probably for a few hours; that song happened really quickly. I wanted to just capture that rural, lo-fi, simple feeling. 

Before “The Weatherman,” I made a whole record that I absolutely toiled on and just hated it. I ended up scrapping the whole thing. It sounded so worked; you could hear the labor in it. So afterward, I went up to the Mountain House recording studio, and camped up there for a while, and “The Weatherman” happened really quickly. Our goal was to have a certain sense of ease around that record. I think I needed to go through that experience, and I feel like the other record is in “The Weatherman” too.

JW: What does success feel like?

Isakov: I love words. I love writing. I love endlessly poring over one little line. Or cutting out a lot of words so that there’s more space, so that you can feel the song more. But for me, it’s a strange feeling the day after playing, you know, with the Colorado Symphony at Red Rocks Amphitheatre. That’s a bucket-list kind of thing, a career milestone, but afterward I feel a little bummed. I think what it is, is that I’m no longer getting ready to create. I think my heaven realm is making stuff. 

JW: What are you reading? 

Isakov: I love John Steinbeck, and I’ve reread a lot of his books. I like his short novels. They’re easy to carry, like a buddy. He would have made such a great songwriter; like the John Prine of writers—really simple, but then he’ll come at you with a line that just blows your mind. I’m reading a book called “To a God Unknown” [Steinbeck’s third novel, published in 1933]. It’s a beautiful story, with some Dust Bowl–era darkness. I also love poetry—again, short simple stuff. I love this poet Billy Collins, and I always get a new one every year, something to bring with me. And right now, I’m reading a compilation called “Nine Horses.”

Gregory Alan Isakov performs this Sunday, November 3 at the State Theatre, in support of “Evening Machines,” with Luke Sital-Singh opening. Doors open at 7 p.m. 


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