About five years ago, Milo Matthews was living in Hawaii and realized he might never leave. The thought didn’t sit well with him.

“I saw myself staying in Hawaii for the rest of my life and playing the same old clubs, doing the same old thing,” the bassist, vocalist, songwriter, producer and engineer said. He was taking a break from planning the next leg of his massive, yearslong, multicountry tour from the confines of the bus he has called home for the last five years. The bus has been parked at the Bend/Sisters Garden RV Resort since November.

“And I put my foot down and I was like, ‘I’m not done yet with what I wanted to do,’” he continued. “So I decided to go on tour. And I was gonna do it by myself because I waited for record companies, I waited to be signed, I waited for all these things to happen, and they did not happen.”

Matthews landed in Denver in early 2015. After a search through Facebook, he found the green bus, a 1985 Ford E350 that was once used for tour groups. “Clarice,” as the bus was known before and after he purchased it, was in Paonia, Colorado, occupied by four adults, a child and a dog at the time.

It seemed like fate: Clarice was also the name he gave his old bass, before he had custom instruments made.

“When I got it, it was so rancid, it was just like, Oh, my God,” he said. “But I knew it, and (the bus’ owners) knew it too, and they really felt comfortable. … I played one show, they saw me play and they’re like, ‘The bus is yours.’”

Matthews hit the road April 15, 2015. His friend and artistic partner, Denver native Lorenda Digiacomo, came on board in September that same year.

They have traveled back and forth across the continental U.S., Alaska and Hawaii; they’ve also toured Germany a couple times. Along the way, Matthews recorded his fourth studio album, “Shapeshifter,” in his mobile studio on the bus, and Digiacomo started her visual art business, Lorendaland, inspired by the deaths of her brother and father.

The final year

This year is the end of the line. Matthews will play his final Bend shows at McMenamins Old St. Francis School on Wednesday and The Brown Owl on Thursday, and then the duo will hit the road one last time Jan. 21.

Digiacomo, who recently purchased her own bus, will part ways with Matthews in February to attend her daughter’s wedding in Denver. Matthews will continue through one last trip across the U.S., through Alaska, Hawaii and Europe, finally ending at the Holler!ween music festival in Northern Colorado in October.

But while the journey may end, Matthews is far from finished with his creative endeavours. He plans to complete a documentary film about his five-plus year journey on Clarice when he finally picks a spot to settle down — and Bend is a strong contender, he said.

“I’m still in the major percentages of moving here after next year, because it’s — I don’t want to say it’s untampered, but it’s still one of the newer places that’s growing and you can feel the vibe from everybody,” Matthews said. “I’ve never gotten any issues about racism or anything like that; it’s been open arms. And that’s actually most places that I’ve gone to, too.”

Through his travels, Matthews has continued to produce and engineer recordings for other artists. He boasts more than 30 production credits over his musical career.

The connection to Bend came about in part because of Matthews’ work with fellow traveling musician Pete Kartsounes, who moved to Central Oregon in early 2017. The two musicians met in Kauai, Hawaii, in 2008 at a jam session at Grateful Dead drummer Bill Kreutzmann’s house.

Matthews first came to Bend in February 2019 to help produce and engineer Kartsounes’ latest album, “I’m Alive.” He also played all bass and drums on the album.

“For me what a producer is all about is getting a fresh ear and fresh ideas on where to take the songs,” Kartsounes said. “Milo and I worked really well together. … I trust Milo; I trusted his musicianship and his professionalism to jump in and maybe just have another set of ears on the songs while we’re laying it down.”

Kartsounes, who spoke from Kauai, where he frequently travels for performances, said Matthews would be a good fit in the Bend musical community should he decide to relocate here.

“When Milo was living on Kauai, we did the album (2014’s ‘Unwind’), and he kind of followed my lead,” Kartsounes said. “He went out and he went heart-first into the realm of being a full-time touring artist. He’s been cranking at it about four or five years now — it’s crazy that much time has gone by. I think it would be great to have him come back to Bend if he could. We’ve been doing some duo shows and some trio shows, and the chemistry onstage is awesome.”

Looping through the U.S.

Matthews is no stranger to travel. Born and raised in Boston, he picked up bass at age 12. By his 20s, he started busking in Harvard Square, and soon hit the road. He spent the next two decades living in various places including Chicago, San Francisco, New Orleans and Seattle.

“After 22 I just went on a Gypsy — I never even thought about getting an RV or a bus or anything like that. Woulda, coulda, shoulda,” he said.

Focusing on solo work, he didn’t join his first band until he started playing with Danny Godinez in Seattle toward the end of his early nomadic journeys. Godinez’s band introduced Matthews to Alaska; he ended up living in the state for more than a decade.

While in the state he developed his signature looping style. Matthew’s music — influenced by the funk and disco he grew up on; his later obsessions with prog rockers such as Rush, King Crimson and Kate Bush; and a deep love of Prince — developed in tandem with the looping. He would eventually add a drum machine and drum pad to his arsenal, while playing higher notes on the bass to imitate other instruments such as guitar.

Since Matthews began looping, the style has taken off with artists such as Keller Williams, Ed Sheeran and (closer to home) Tony Smiley adopting the devices. Early on, Matthews drew inspiration from early bass loopers such as Victor Wooten, Steve Bailey and Living Colour’s Doug Wimbish.

“I started bringing it to the forefront, and I like to say that I was a part of helping out with the looping revolution, because people saw me do that and they were just like, ‘No way,’” Matthews said. “But it made a lot of musicians apprehensive because they were like, ‘I don’t even know what you’re doing, bro.’ I was like, ‘Dude, it’s so easy.’”

Finding a kindred spirit

After his divorce, Matthews moved to Hawaii. He lived there for about five years before he got the travel bug once more. One bus named Clarice later and he was on the road.

Digiacomo worked as a legal secretary in Denver when she met Matthews in 2015, but also spent 15 years as a flight attendant. Like Matthews, she was looking for a change.

“I just knew there was something different for me,” she said. “People at work were like, ‘You should do this,’ ‘You should do this.’ I’m like, ‘You know what? When the right thing comes along, I’m gonna know and I’m gonna jump.’”

She met Matthews at one of his Denver shows. Matthews had produced an album by Alaska outdoorsman and musician Marty Raney, and Digiacomo designed the cover art.

“Marty was like, ‘You should go check out Milo, he’s a genius,’” Digiacomo said. “And I was like, ‘It’s a Thursday night, I have to get up at 4.’ But I went — I just kind of knew I was supposed to go. And I’m not — Milo knows — I don’t go out and do a whole lot ever. So I couldn’t find anyone to go with me, (but) I’m like, I’m gonna go and check him out. I loved his music, and we kind of became friends over that next year just through Facebook.”

On a whim, Digiacomo joined Matthews on his first Germany tour (she was able to fly for free thanks to her earlier flight attendant work). She’s stuck with him ever since.

“I was like, ‘Hey, I don’t know anything about music, but I’ve handled nine attorneys; I can surely figure out how to book one musician,” she said. “… I’ve learned a lot being on the bus, and Milo’s best friends — family — now, forever. And through all that, the Lorendaland came about. My brother had passed away; my dad passed away last year (in April 2019). I started painting rocks and making things.”

Documenting the journey

The documentary will focus on all of this, as well as shining a spotlight on other artists the duo met in their travels.

“I’ve got about eight people (who are) gonna be showcased in the movie,” Matthews said. “We’re gonna just tell a five-minute blurb of their things under the subject of entrepreneurship and following your dream and focusing on that, and the choices that we make and why we will never give it up because that’s who we are.”

The tour hasn’t come without its challenges, Clarice being one of the biggest. Matthews and Digiacomo have replaced the bus’ engine three times, its transmission twice and the alternator three times, among other maintenance and repairs. They estimated they’ve put about $30,000 into the bus. (In addition to income from shows and Lorendaland, they’ve relied on major contributions from three donors, as well as smaller donations via PayPal and a Patreon, patreon.com/milomatthews, for the documentary.)

“Learning how this vehicle works was half of my job too, because I got under the bus; I was figuring out things; I cut corners,” Matthews said. “But also we had just bad luck with bad mechanics.”

Matthews finally found a mom-and-pop mechanic in Truth or Consequences, New Mexico, for the third engine replacement, and the bus has hummed along ever since.

The documentary also helped save the tour. About four years in, Matthews was in Germany for another round of shows and was about ready to give up.

“I’m in Germany and it’s like so much has happened — the toils and trials of being on the road and touring, and the money and the finances — I started getting tired. I started getting fatigued. I kind of reached the down low,” he said. “And when I was in Germany, I really had thought, ‘OK, I think this is it; I think I’m really done playing or doing it this way. I think I may stay in Germany.’ And I was just like, ‘You know what, I think the tour is over.’ And I spent the whole month of last October trying to figure out what I wanted to do. And then one morning I woke up and actually had a dream about it where I was wrapping up making a film, and then I woke up and I was like, that was it. That was the one saving grace, was like, ‘You know what, I should make a movie about this.’”

Reporter: 541-617-7814,


(1) comment


Enjoyed a brief set at Sisters Coffee's anniversary celebration. Very talented musician. What a great backstory!

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