When you’re booked to play a two and a half hour gig, you’ve got to pull out all the stops.

That’s what Dustin Bentall had to do when he first came to Kingston six years ago, he tells me, softspoken on the other end of the phone.

“I played the Merchant to about four or five people. I was really green — it was the first time I had ever gone out on the road,” he said. “I had to play three sets, 45 minutes each, I didn’t even know that many songs.”

Bentall said he used every resource he had.

“I had to play every single song I’d ever written up to then and pretty much every song I knew,” he said.

No longer new to the scene, the psychedelic country singer is returning to Kingston with his backup band The Smokes as they tour with country star Lindi Ortega.

While some may get homesick spending weeks on the road, for Bentall, home is wherever his van takes him.

“I’m not the type of personality to have a steady job and live in one place — I love to be on the move,” he said. “All the people I’ve met across the country, the friends I have, I never really feel far from home.” His latest video for “You are an Island” just premiered on CBC boasting a melody as meandering as Bentall’s tour schedule.

The track appears on the band’s latest EP Orion.

Like many musicians, Bentall said that picking his favourite song to play live is like “picking a favourite child.” He takes a moment to ponder my question, and then offers up “Orion,” the title track from his October EP.

“Something happens during that song that sparks a connection with the crowd,” he said. “I don’t know exactly what it is.” Although Bentall said he couldn’t put his finger on why it was a crowd pleaser, he credits it partially to it still being largely unfamiliar repertoire for the audience.

“I’m not 100 per cent comfortable playing it, which can be a good place to be,” he said. “If you know something too well you don’t have to think about it … there’s a stronger energy that’s happening here.”

Dustin Bentall and the Smokes play The Grad Club Friday at 9 p.m.