Courtesy: Alysse Gafkjen

The two-plus years since 2015 have been a time of transition for Gill Landry. The multi-instrumentalist left Old Crow Medicine Show (with whom he sang and played banjo, and won two Grammy Awards). His fiancé left him. He packed his bags and left Nashville, too, after no longer hearing the city call to him.

Landry, a singer-songwriter, also recently released his fourth solo album, on which he addressed the heartbreak of lost love and the need to move on. Love Rides a Dark Horse is an intricately crafted slice of country, roots and crooner pop that moves not at the gallop of Old Crow Medicine Show but at its own observant pace.

“I left [OCMS] because I couldn’t do both [that and solo work] and give everything I needed to either, and I was more into where I’m headed now,” Landry said in a brief email conversation in between a European tour and a West Coast jaunt that will see him opening for Valerie June at the Fillmore on Monday.

Love Rides a Dark Horse is filled with moments of hope; the name is a callback to Gill Landry’s hope that he will win happiness in the end. He produced and mixed the record on his own, and recorded with a bevy of friends, including fiddler Ross Holmes (Mumford & Sons, Bruce Hornsby), keyboard player Skylar Wilson (Rayland Baxter), drummer Logan Matheny (Rosebuds), with harmonies provided by Klara Soderberg of First Aid Kit, Karen Elson and Odessa.

But his baritone voice rises above the rest of the mix, with flourishes of fiddle on tracks like the Springsteen-esque “Denver Girls,” as well as organ and pedal steel, such as on “The Real Deal Died.” Landry isn’t wary of putting his eggs in one basket with his solo music, nor he should be.

“Same road, different vehicle,” he said.

How were you able to get such a stellar cast behind this album; Klara Soderberg, Karen Elson, Logan Matheny and all of the others? Are they friends of yours?

Yeah, friends. I always feel honored when talented people I admire are into what I’m doing. I don’t overly plan these things. I just go with what feels right. I had been hanging out with Karen in Nashville and just asked if she’d sing one. Logan I’ve known for years, and I totally trust his instincts; met Klara at a Laura Marling show I played in Manchester and caught up with her while in Stockholm. If I over-planned these things, I don’t feel like they’d be as good.

Are there other artists you’re working on talking onto your next album?

I don’t overly plan these things; usually just [it’s] people who are in my life at the moment, and I’m not there quite yet with the next album.

The album was unfortunately the result of a break in a serious relationship. Did you debate whether to take the songs in this direction?

Not really; I just write what I know. I feel most songs start out as therapy for me, and if they resonate with others, I’m happy.

One of your changes was giving up on Nashville after a decade. Even though you haven’t officially moved anywhere, and you’re living out of suitcases, tell me why you outgrew your city and what your plans are going forward?

If the horse don’t pull, you gotta carry the load. As far as moving forward, we’ll see what the future holds. My plan is no plan. So far, so good.

Much of the lyrics on this album are heavy, and yet the melodies are very airy; not light, but not hurried, and exuding some type of “I’ll be all right” swagger. How did you accomplish that mood?

I can’t define that stuff. It is what it is and comes as it does.

Writing this record must have had a good amount of inner reflection. Were the songs also a joy to write and record?

I enjoyed it. I sit down and write words until they come together. Sometimes a melody comes first; sometimes later, and then I just follow it down the rabbit hole and hope it’s not a piece of shit.

You produced and engineered the record all by yourself. There are lots of great flourishes, whether brass or pedal steel, some fiddle, that sweep in and out. Did you find what you were looking for through experimentation, or did you already know what you wanted at the outset?

I never know what I’m looking for, and for me that’s the great pleasure in all of this. If I knew exactly what I was looking for, I probably wouldn’t do it. It’s not about the outcome for me as much as the process.

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