DIY Diary: Day 30

Musician and Midbrow reviewer Ty Maxwell documents his DIY solo tour across the Northeast.

· 4 min read
DIY Diary: Day 30
The author (right) at a backyard show in Medford, MA.

Day Thirty: Thursday, September 4rd, 2025 – Nate’s House (Medford, MA) with Alexander, How Strange It Is, Babytooth

For this series of articles, our writer Ty Maxwell will be documenting his tour of the Northeast, spanning from August 6th to September 8th. Maxwell will be writing reflections and insights into the process of booking and executing a DIY tour as an independent artist, the relationships that enable the whole enterprise, and the general day-to-day experience: the minutiae, difficulties and triumphs involved in touring as a solo musician.

For the last thirty days, I’ve been traveling basically totally alone. This is that real tour minutiae: I’m usually driving at least a couple hours a day, something like 150 miles, maybe much more, maybe less. No crazy-long drives, except when I’ve gone straight from Boston to New York, which, as previously mentioned, was especially smacked on Labor Day weekend. When I was in Maine, I interviewed a DIY lifer who shall for now remain nameless, and I asked him about what he used to do to kill time on long drives:

Long drives, I love ‘em. I used to rent, or check out from the library, language courses, on CD. And just like, learn a language, or try to learn a language driving across the desert, being like, “Aquí Bianca? No. Bianca non aquí.” [laughs] Randomly learning Italian for no reason.

I only went on my first solo tour a couple years ago, after a decade of doing the band thing exclusively: bodies packed like tinned fish in the van, gear and pillows and backpacks stacked high, chips of various origin (pita, tortilla, potato) mashed into particles on the floors. The first time I traveled fully solo I felt some light trepidation going into it, wondering how I’d adjust, but I quickly found I loved it. With the band tours, I’d start every new morning with people, and after driving together for hours, the first thing I usually wanted or needed whenever we’d reached our destination was a little alone time, a little peace and quiet, a little air not thickened by the aroma of various BO’s. Now, traveling alone, I get to listen to whatever I want – podcasts no one else I know likes, whatever music I'm in the mood for, relative silence, talking to myself (without anyone in earshot thinking I’m crazy) – and then, landing in whatever town the show’s in, I’ll feel eager and excited to see people, to talk and connect.

So it was a break from routine to have Isabel, from the band Babytooth, hop in my car for the drive from Burlington to Boston, a city she’d never been in before, and one I have a long history with. Boston was the first place I ever played outside of my home state (Connecticut), back when I was 18; my high-school-slash-gap-year band played at the late, great Great Scott, in Allston. I still have the flyer in a shoebox of trinkets and ephemera somewhere. I mostly went to college in New England, and used to go to Boston on weekends with such frequency that I had friends there that assumed for years that I also lived there, that I just went to a different school. Isabel and I met for the first time at the Woodstock show I played last week and were getting along great — but this was the first time we really sat down and talked one-on-one for a long stretch.

Over the course of the three-hour drive, Isabel and I got real, talking about our parents, siblings, dating, and various motivations for art-making. Musicians and songwriters and artists who don’t come from artistic families often talk about chosen family – which reminds me of Andrew Solomon’s book Far From the Tree, and his notion of “horizontal identity,” as in the identities you have or form that aren’t derived from or shared with your parents – and as amazing and life-affirming as these affinity bonds can be, I often pause to reflect on the loss I feel when I realize how few of the friends I’ve made through art, through touring and playing shows, have met my immediate family, and how few of theirs’ I’ve met, or know anything about.

It’s a different kind of depth you feel when you know that side of someone’s life, especially deeper into adulthood. Isabel and I both admitted to each other that we sometimes wish our parents understood us better, or took more of an interest in these weird life choices we’ve made in the name of making and sharing music; I often wonder what it would have been like if they’d been artists, too. As I get older, though, I’m mostly happy they care at all, that they show me any interest, that we love each other despite misunderstandings. They did so much to facilitate my becoming this person in the first place, that they’re still here. Something else Solomon said in the book, which has stuck with me ever since I read it over ten years ago (he was speaking of children, but I think the same is true of parents): “When we love them, we achieve above all else the rapture of privileging what exists over what we have merely imagined.”

Rolling up to Jordan’s friend Nate’s backyard in Medford, just outside of Boston, I was thrilled to learn that Jordan’s parents, and two of his aunts, were going to be at the show. (“It would be crazy if all of my aunts came – they almost did, they were talking about it,” Jordan told me later.) Just another sweet coincidence, all of them being in the area at the same time, Jordan over three thousand miles from his home. Nate’s parents would be there, too, along with their sister Ella (best known as Squirrel Flower), like we’d Venn Diagrammed the gig with a family reunion. Alexander, the Boston musician, poet and songwriter who played first, excitedly shared that he saw his very first shooting star during Babytooth’s set; it was that kind of night, a late-summer hang, school back in session for the teachers in attendance, new and old friends all together. Jordan spoke briefly and passionately during his set about Gaza, about how everyone deserves the freedom and safety to gather like this, to share songs and poems and stories, with whatever families we’ve got, and the families we’ve yet to make, that might yet be. It was a good word: painfully, heartbreakingly true.