For more than three decades, Skydiggers have been crafting timeless, harmony-rich songs that resonate with the heart and the head. With their latest album, Dreams & Second Chances, founding members Andy Maize and Josh Finlayson return with a collection that feels both intimate and expansive—a natural evolution for a band that knows how to finish each other’s musical sentences.

Born from simple kitchen jam sessions and built on instinct and trust, Dreams & Second Chances explores themes of love, loss, memory, and hope. From the tender reflections of “I Love You, Too, Maybe…” to the Gord Downie-inspired “Walk With the Stars,” the album captures Skydiggers at their most open and inspired.

On May 24, the band will bring these new songs—and plenty of fan favourites—to The Broom Factory in Kingston (web link). Ahead of the show, we caught up with Andy and Josh to talk about the making of the album, their connection to Kingston, and what fans can expect from their upcoming live performance.

Q: "Dreams & Second Chances" feels very instinctual and heartfelt, built from those kitchen song sessions. How did working in that spontaneous, trust-driven way shape the songs compared to past albums?

Josh: All recordings are different, this one being no exception. The band has been playing really well and has created its own identity to our live shows, and this translated into this recording session. I think they are performing as collaborators, which we encouraged and wanted to capture. Everyone seemed invested and empowered. Recording at the Bathouse with Nyles Spencer engineering helped facilitate this as well. Nyles understands the importance of keeping the session moving and we trust his instincts. It's a great document of this version of the band.

Andy: It was an exhilarating feeling to have all of the songs come together as quickly as they did… it's a real testament to the musicianship and friendship that exists within the band.

Q: The album touches on themes of love, loss, memory, and hope. Was there a particular moment or song that unlocked the emotional core of the album for you?

Andy: There were so many special moments during the 5 days we were at the Bathouse—both musical and personal—but if I had to pick one song that unlocked the emotional core of the album for me, I think it would have to be "Dreams and Second Chances."

Josh: I think there was a conscious effort to recognize the need for some positive energy that music and songs can provide. The world seems disconnected and polarized over the last number of years. I feel the themes you mention above are reflected in these new songs.

Q: "Walk With the Stars" is a tribute to Gord Downie. Could you share a bit about the connection there, and how that song came to life?

Josh: Skydiggers met The Hip in 1990 when our first recording was released, doing some shows together. That started a life long friendship. Gord Downie lived in Toronto, and he and I became close and started playing music together. Ultimately, it led to his first solo recording, Coke Machine Glow. Many solo records and tours followed that I participated in. The final collaboration being Away is Mine, released after he passed away. I co wrote "Walk With the Stars" with Jim Bryson, who toured with The Hip as a band member for their We Are The Same record. When we were writing this song, I thought about our shared experience and friendship with Gord and thought the "Walk With the Stars" line was a good way to make that connection. [Referencing Gord’s Lakota spirit name, Wicapi Omani, man who walks among the stars.]

Q: Dreams & Second Chances was recorded at The Bathouse, just outside Kingston—a place with deep ties to The Tragically Hip. What drew you to record there, and how did that setting, with its history and connection to Gord Downie, influence the vibe or spirit of the album?

Andy: Skydiggers have recorded at the Bathouse several times in the past. We love the feeling of creativity that permeates the studio and the history of all of the legendary recordings that have been made there. You can feel the inspirational presence of Gord S., Paul, Robbie, Johnny and Gord D. at all times.

Josh: I recorded many records with Gord Downie and other artists. It’s a special place with many great memories for me. I always feel Gord’s presence while I’m there. The Hip set up the studio for bands and musicians to create and collaborate in. It’s an amazing creative space. Very unique. I feel very fortunate and grateful to have spent all the time I have making music there.

Q: Skydiggers have always been known for beautiful harmonies and that roots-rock heart. On this album, it sounds like you’ve expanded the sonic palette. How did you strike that balance between staying true to your sound and exploring new textures?

Josh: I think the band members expanded the sonic palette on this record. They are all terrific musicians and have raised the bar for Andy and I in such a significant way. I don't worry about staying true to our sound. I love exploring new ideas, sounds and textures.

Andy: We'd have to give credit for the expanded sonic palette on this album to our bandmates and collaborators Jessy Bell Smith, Aaron Comea, Noel Webb, Michael Johnston and Derrick Brady. Josh and I can't help but always sound like ourselves, and therefore true to our sound.

Q: The album’s title, Dreams & Second Chances, is evocative. What does it mean to you personally—and what do you hope listeners will take from it?

Andy: That it ain't over 'til it's over… that there will always be more living, laughing and loving to be done.

Q: You’re playing The Broom Factory in Kingston on May 24. For fans who might be seeing Skydiggers live for the first time—or for the first time in a while—what can they expect from this show?

Josh: I think they’ll see the best version of the band ever!

Andy: A most excellent evening of roots-rock that will hopefully move you… and your feet.

Q: Live shows always bring songs to life in new ways. Are there any tracks from the new album you’re particularly excited to share with a live audience?

Josh: For sure. We can't play all of them, but “Snow Blind”, “Dreams and Second Chances”, and “Start Again” are a few I know we’ll perform. We will play some others as well. The trick is to balance out older tunes people want to hear with a few new tunes dropped in.

Q: Your band has been making music together for decades. What keeps the live experience fresh and exciting for you?

Andy: Being on stage with my friends and bandmates playing songs I never tire of for an appreciative audience.

Josh: Every show is different. Being present is what keeps live shows fresh and exciting to me.

Q: You started each day of this album with a song played in the kitchen—there’s something very grounding about that image. Do you see this album as a return to the roots of why you started making music in the first place?

Josh: Over the years of making records, I like this process of introducing songs to band members/musicians. First thought, best thought. Not always, but it’s usually a good starting point. You get to present the tune in its most basic format. They listen and think about the possibilities. Then you head into your stations and start playing. Often, rehearsing before a recording can make changing direction difficult. This allows for changing quickly much more easily.

Andy: I think Josh and I have never strayed from the roots of way we started making music together in the first place: Trying to write timeless songs in the singer/songwriter tradition of our musical heroes like Gordon Lightfoot, Hank Williams, Jimmie Rodgers, Joni Mitchell, Neil Young, to name but a few of those who have inspired us on our musical journey.

Q: After all these years, what’s something about Skydiggers that you think still surprises people when they see you live or discover your music for the first time?

Josh: Probably that we’re still making recordings and playing shows after all these years.

Andy: I don’t know… I’m still being surprised by the band after all these years – and loving it!

Don’t miss the chance to experience Skydiggers live in Kingston, where their signature harmonies, heartfelt songwriting, and the fresh energy of Dreams & Second Chances will come to life on stage. Catch them at The Broom Factory on May 24 for an evening of music that feels both nostalgic and new. In the meantime, give the new album a listen—it’s a beautiful reminder of why Skydiggers remain one of Canada’s most beloved bands. Details and tickets available here: web link Posted: May 20, 2025