Deep Dark Woods brings haunted sound back to city

The more things change, the more they stay the same. Time, after all, is a circle.

For Ryan Boldt, singer and principal songwriter for the long-running, award-winning Canadian folk-rock outfit the Deep Dark Woods, that circle remains unbroken.

“I’ve been playing in bands and going on tour for over half my life now,” Boldt says with a laugh. “It’s really bizarre to think about.”

Founded in Saskatoon in 2005, the Deep Dark Woods has released seven albums of original music, along with two followup volumes to Boldt’s Broadside Ballads series of traditional folk songs.

“When I first started the band, I was the young guy. Now I feel like an old man,” Boldt admits, laughing again. “When I first came to Winnipeg, we opened for the D-Rangers at the Times Change(d). They were the established band at that point and that was over 20 frigging years ago now.”

Boldt is DDW’s lone original member, though organist Geoff Hillhorst has been with the group since 2009 and Mike Silverman has been on drums since 2015, forming the core of the group which began touring regularly again after the COVID-19 pandemic put a temporary halt to live performances in 2020.

“I was busy as hell prior to that, but that stopped everything, and it was a slow process of getting it back to where it was before. The whole break was nice, for me. I was on the road for 15 years solid. I needed that couple year break, and now I’m antsy to get back on the road,” Boldt says.

Tonight, the Deep Dark Woods return to Winnipeg for the first time since October 2017 for a show at the Park Theatre.

“It’s been a long time,” Boldt admits.

In the meantime, though, Boldt has kept himself busy. The band recorded its 2025 record, The Circle Remains, with producer David Parry (of the Victoria, B.C., band Loving).

“He’s got a fully analogue studio just outside of Nanaimo, this big stone house we recorded in,” Boldt says.

The 11-track platter contains all the haunting hallmarks of a Deep Dark Woods record. Songs of heartbreak, yearning and sorrow are complemented by sparse, subtly psychedelic arrangements, with Boldt’s lonesome tenor front and centre.

More recently, the band released the single East of the Sun, a song by English folk singer Roy Harper, which Boldt recorded in his home studio in London, Ont. He also spent some time in Nashville recording a four-song EP with American singer-songwriter Erin Rae, whom the band toured with through Europe last year.

“She’s amazing,” Boldt says.

As if that weren’t enough, Boldt and his wife also have a three-year-old at home.

“We’re very busy and it’s tiring. Before, I’d go on tour before and I felt tired after I got home. Now, I go on the road and it’s kind of a break from it all,” he says.

Domestic demands notwithstanding, Boldt still finds the time to read and write regularly, the process just looks a little different than it once did.

“When I was younger, I would just wait until it came out of me,” he says. “Now, I have to make time to do stuff. I’m just writing down little lines here and there. Then I go into the studio and try to construct them all together to create a story.”

Reading about the particular processes of songwriters he admires has helped that Boldt refine his own approach to his craft.

“It’s inspiring. A lot of people do it nine-to-five. I always used to beat myself up before. I think I’ve been able to train myself not to. If something’s not great, at least I did something,” he says.

One way or another, this far into his career, Boldt can’t see himself doing anything else.

“I love doing it. There’s no better feeling. There’s a satisfaction you get from finishing something that I can’t get from anything else,” he says.

And these days, he’s not taking anything for granted, either — not least the process itself, which Boldt describes as “delicate,” almost mystical at times.

“After I write one, I think it’s probably the last one I’ll ever write again.’

sheldon.birnie@winnipegfreepress.com