He’s built a devoted fan base through more than a dozen years’ worth of releases – most on Chicago indie label Drag City – and consistent touring. Oldham’s approach to the road, however, differs from most of his contemporaries: He’s more likely to announce a month-long tour of a single European country than a nationwide theatre trek.

This August, he did four shows in two days at Joe’s Pub in New York City, followed by a round of free in-store performances at record shops across the Midwest.

A rare tour of major theatres is booked this fall, with 15 dates planned across eight West Coast cities. The concerts will feature a full band and will follow the September release of his latest album, The Letting Go.

Oldham told Pollstar the evolution in his touring habits came in two parts.

“The first thing that happened was I started to get frustrated, basically, by going from place to place and not spending any time in any given place,” Oldham said. “So it started to seem like it’d be better if we could do more shows closer together.

“The first big trip we did like that was about five or six years ago. We did the West Coast and took three weeks to play three states, as opposed to doing what we used to do, where in three weeks we could get from Texas to Washington state.

“In order to do that, we had to seek out lots of different smaller towns to play. But it meant that the drives were less, and we could meet more people and just feel as if we’d really been someplace, and that the place where we were could affect how we were playing, rather than just sort of whizzing through all the time,” he said.

“And then the other thing that happened was some of the bigger places like New York, Chicago, Los Angeles and London began to just be more and more of a hassle to play. Because, you know, unfortunately,” he laughed, “the audiences are bigger and the records sell more.

“I don’t really like playing in big places,” he continued. “And with all of the chaos and logistical nightmare that the big markets are to go into and play, I just started to think, well, if we can just go into those places every four or five years, you know, as long as we keep playing for people …

“Some people can travel. And almost nobody’s from those big places anyway, so we have a chance of hitting them when they’re visiting home.”

And when it comes to performing overseas, Oldham has made a point of getting his plane ticket’s worth.

“Now, when I go to Europe, I usually like to do a tour of Italy – that’s it – or do a tour of Spain. This year, I did a tour of New Zealand and then I did a tour of Scotland. We spent three or four weeks over in Scotland and Ireland but we didn’t play England, we didn’t play France – we just were there. And it was so nice.

“Then I could come home and people could say, ‘Boy, you went to Scotland!’ and I could say, ‘Yes, I did!’ You know? I did see Scotland – I met a lot of Scottish people, I ate Scottish food, I learned about Scottish music. Which I didn’t used to be able to do because it wasn’t about that at all.”

But isn’t it harder to tour in smaller towns, where less fans are likely to have heard the music?

“In some ways it’s easier,” he said. “It’s just a matter of finding the right people, which takes time and is difficult to do.

“For years, I wanted to play in Italy. There were a couple times where something was scheduled and then it was canceled and the booking agents would say, ‘Yeah, Italy’s impossible. There just aren’t any shows in Italy.’ And for years, I thought that was the truth.”

Then one day, a friend from the Italian band Uzeda contacted Oldham and asked if he’d like to tour the country. He enthusiastically agreed, and soon had a two-week tour on his hands.

“Every show was different,” Oldham said. “Sometimes we’d have huge crowds in small places, or teeny weeny crowds in huge places, but it worked. We made enough money to cover expenses and a little more.

“It’s just reaching out and realizing that any place that you would want to play, there’s probably somebody there who would want to hear the music. Whether it’s just a local person who just wants to hear anybody that would come to their town, because nobody does, or because there’s – especially now with the crazy distribution that the Internet allows – people all over the world who can be turned on to music and are waiting to hear it come to them.”

Oldham has played in all but five U.S. states – the Dakotas, Wyoming, Alaska and Hawaii – and had hoped to do a tour of those five this summer. Grouping the states together proved unfeasible, but he plans to hit several Alaskan cities next year.

Despite his professed aversion to large venues, Oldham has made notable exceptions. As the opening act for Bjork on her last North American tour in 2003, he played to outdoor crowds of more than 10,000 armed only with an autoharp.

“It was definitely strange, but I got a lot out of it,” he said of the experience. “I did it as a one-man thing because the main reason for doing it, I thought, would be to learn about these places and how Bjork puts her tour together, and to meet people, and I thought I would have a greater chance if I was traveling alone than if I was traveling with friends.

“Because if I was traveling with friends, we’d spend all of our time with each other. Alone, I could just watch everything and see how everything went and just be there as a free agent.

“I also figured that no matter if we were playing with a band or alone, the chances of turning anybody on were going to be minimal, because they’re Bjork fans, and they spent a lot of money to come to a Bjork show.

“I know that if I go see somebody, I’m not going to see who’s playing before that person. God bless whoever that opening act is – that’s not why I’m there. I know it’s happened, but it’s a handful of times where an opening act has made an impression on me.

“I think that’s why people tour with bands, mostly – ’cause they think that they’re going to turn people on. But I don’t have that kind of confidence,” he said, laughing.

“I just figured, you know, I’m there, I’ve got a guarantee every night – I might as well learn an instrument. So I chose the autoharp.”

The fall itinerary for Bonnie Prince Billy includes some smaller gigs, including the tour launch at McCabe’s Guitar Shop in Santa Monica and two shows among the redwoods in Big Sur. However, he’s also booked three nights apiece at the Mission Theater in Portland, Ore., and St. James Hall in Vancouver, B.C., in addition to a two-night run at San Francisco’s Great American Music Hall.

“I figured, if we’re going to go to these cities, rather than play big halls – which aren’t fun to play – we could play the smaller halls and then just maybe try to give the tour its own integrity unto itself, by basically having it be these big-city experiences but trying to make them more satisfying than they could be otherwise,” Oldham said. “To try playing big cities, but maybe just treat them like small towns.”