Mysha Caruso had a dream.

And then when he had a chance to fulfill that dream, he passed it up in favor of music.

On Wednesday, the current fruits of that decision, Ashland-based indie-folk trio Kites & Crows, will play a free show at McMenamins Old St. Francis School in Bend (see “If you go”).

Caruso and his band mates — Jesse Baldwin (banjo/accordion) and Nancy Martin (cello/vibraphonette) — are excited, not just for the Bend date, but for their first summertime tour and all the fun things it brings: swimming holes, outdoor shows, leaving the coats at home.

The band’s previous tours were confined to the late fall and early winter, after the end of the Oregon Shakespeare Festival’s season. All three members work for the festival; Martin is part of the house staff, Baldwin is a lighting technician, and Caruso is a stagehand.

Caruso, who is Kites & Crows’ primary singer-songwriter, arrived in Ashland in early 2007 after several years in Hawaii and a childhood in Massachusetts in which he dreamed of someday working as an actor at the Oregon Shakespeare Festival. At his East Coast performing arts school, he had teachers who knew of the OSF, so the festival was “always on his radar,” he said in a telephone interview Tuesday.

“I got a little sidetracked in a good way,” he said. “I was backpacking through Hawaii, met a girl and we ended up staying on the island for seven years. There wasn’t much theater going on in Hawaii, but I had a guitar with me and I started writing some songs ... because there wasn’t much else going on.”

Eventually, the desire to tour pulled Caruso back to the mainland, where a cross-country jaunt deposited him in Ashland too late in 2007 to audition for plays, but just in time to snag a stagehand job.

It was enough to put those old acting dreams on hold.

“They were like, ‘You’re grew up in theater. You’re very qualified. Come on as a stagehand and then you can audition for next year,’” he said. “But by then I had fallen in love with being a stagehand and I was making music.

“I kind of lost the acting bug,” he continued. “I love all the actors at the festival. They do such a great job. But I’m really liking being behind the scenes.”

Only history knows what kind of actor Caruso was. But as a songwriter and musician, he’s an up-and-coming leading man. Formerly a member of the alt-country band One Horse Shy (which dissolved last year after playing Bend several times), Caruso found Baldwin through the OSF’s virtual bulletin board.

“I put out an e-mail that said ‘Established singer-songwriter seeks collaborators’ and within a day Jesse replied with ‘Established collaborator seeks singer-songwriter,’” he said.

The two began playing around town and touring, and then they found Martin at an OSF function. Over the past couple of years, Kites & Crows has produced a handful of independent releases, including its current seven-song EP, “Villager.” (Stream lots of K&C music at www.kitesandcrows.net and www.reverbnation.com/kitescrows.)

The band’s songs deftly walk a line between vintage folk and modern Americana, reflecting Caruso’s influences, which range from his parents’ record collection (Bob Dylan, Simon & Garfunkel, Joni Mitchell) to a current wave of acoustically rooted artists (Ryan Adams, Jim White, The Decemberists). The songs on “Villager” feature all of what makes Kites & Crows a band worth watching: Caruso’s warm, rich vocals and compelling melodies; Martin’s solid, swooning cello parts and occasional harmonies; and Baldwin’s banjo, which clicks along like the guts of a well-tuned clock.

It’s exactly the kind of melodic indie-folk sound that Oregon has become known for, not only in Portland’s white-hot music scene, but in smaller statewide outposts like ... well, like Ashland. And it’s a sound that has carried more than a few artists — think The Avett Brothers, Ray LaMontagne, Old Crow Medicine Show — to stardom in recent years.

Whether Kites & Crows will follow a trajectory similar to those artists remains to be seen. For now, Caruso and company are “all smiles” and appreciating the opportunities afforded by their biggest tour yet. (They’ll play before The Decemberists at the Britt Festival in Jacksonville later this month.)

“It’s been a steady climb,” Caruso said, “but it really feels like things are moving in a great direction.”