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On Oct. 31, while much of the country revels in Halloween activities, bluegrass-Americana powerhouse group Greensky Bluegrass will officially celebrate its 25th anniversary.

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The group first launched during an impromptu house party performance on Halloween night in 2000 in Kalamazoo, Michigan, a performance that has evolved into a musical journey that has brought the five-piece group to headlining festival main stages and selling out venues throughout the country, including recently spearheading their 20th show at iconic venue Red Rocks. Since issuing their debut album Less Than Supper in 2004, Greensky Bluegrass has notched two Billboard Bluegrass Albums chart-toppers, with 2014’s If Sorrows Swim, and 2019’s All For Money.

Greensky Bluegrass will commemorate its silver anniversary by returning to its hometown roots with two shows at Wings Event Center in Kalamazoo on Oct. 31 and Nov. 1, but also with the release of new album XXV, arriving Friday, (Oct. 31) on Big Blue Zoo Records/Thirty Tigers.

“It’s the first time that I’ve ever actually slowed down enough to look back and it’s worth celebrating, because so many bands don’t even get a chance to do that,” Greensky Bluegrass dobroist Anders Beck tells Billboard.

On XXV, Greensky Bluegrass reimagines many of its most well-loved songs, captures a couple of live-show staples for the first time, and welcomes a strong roster of collaborators, including Sam Bush, Lindsay Lou, Nathaniel Rateliff, Aoife O’Donovan, Holly Bowling and Greensky Bluegrass’s fellow Michigan native, Billy Strings.

“It wasn’t about, like, ‘We want really big, important guests on this record.’ It was calling friends,” Beck says. “It’s almost like a family photo album. And it was fun to reimagine the songs. When you finish a record, you’re trying to make the penultimate version of that song, and then to get to redo it 10, 15, 20 years later is pretty cool.”

On XXV, Rateliff joins on “Past My Prime,” while Bowling joins on “Last Winter in the Copper Country” and “Windshield.” Previously-recorded songs such as “Old Barns” and “Windshield” get fresh patinas, but the album also sees live-show favorites such as “Who Is Frederico?” and “33443” make their initial appearances on a recorded Greensky project.

The band’s name has long embodied the group’s nimble balancing act of being rooted in and familiar with bluegrass traditions while also using it as a launching pad for exploring other, often contrasting, musical styles. In the process, Beck and his bandmates Michael Arlen Bont (banjo), Dave Bruzza (guitar), Mike Devol (upright bass) and Paul Hoffman (mandolin) became trailblazers for the acceleration of the freewheeling, jamgrass movement over the years, a style that now fuels live shows for artists such as Strings.

“A lot of these arrangements and guest spots were born out of the live shows—In fact, most all of ’em,” Beck says. “The things with Holly Bowling, she’s essentially the sixth number of our band. And Lindsay Lou, she wrote a key part for the song ‘In Control’ live, just singing with us one day.”

Strings joins on a revamped version of “Reverend,” which originally was included on Greensky Bluegrass’s 2008 album Five Interstates. The group first met fellow Michigan native Strings when he was a precocious teen, and Strings was opening shows for Greensky Bluegrass before his ascent to headlining arenas.

“He’s played ‘Reverend’ in his shows, and it’s funny, with him, he could sing most of our songs,” Beck says. “I think at the first time we met, we went to a campground and jammed all night around a campfire. That was the beginning of the musical friendship, if I recall correctly. I remember he seriously was like, ‘How do I jam these tunes?’ And I remember my answer being like, ‘First, you stop stopping,’ which is totally true, and it’s also right in line with my sense of humor. Bluegrass songs are concise, and he was into real traditional stuff. Then he was on tour opening for us for a long time and he’s an incredible musician.”

The Bowling collaboration of “Last Winter in Copper Country” took place during the COVID-19 pandemic, during the recording sessions for the group’s 2022 Stress Dreams album. “We went into the studio and they basically gave us the keys and said ‘See ya.’ So, we had her come play on this song and the six of us were in the room together and it just felt great to just jam again.”

New Grass Revival founding member and progressive-bluegrass luminary Sam Bush joins them on a rendition of New Grass Revival’s 1987 song “Can’t Stop Now.”

“Sam’s a hero who’s become a friend,” Beck says. “I was in the studio with Sam and basically producing the song for the band a bit, and that was one of those ‘How did I get here?’ moments. Sam later brought me the little 45 record, the radio edit, of the New Grass version of ‘Can’t Stop Now.’”

Over the years, the group has forged a sound that isn’t easily categorized, blending and bending sounds along a spectrum of bluegrass, folk, Americana, jazz and rock. The band’s concerts have become a hallmark of improvisational energy that has attracted a devoted and eclectic fanbase.

“I think something that’s always been important, is it’s a collective of individual humans, and that that’s why we’ve got so many eclectic sounds,” Beck says. “It’s bluegrass, but also rock n’ roll, it’s all those things. Our fans encourage risk-taking, musically. And that’s what I love about it so much—failure is totally an option in a jam, as long as you’re teetering on the edge.”

He adds, “That’s what keeps this music alive for 25 years, it’s always evolving live. The band is so locked in on an improvisational level that I’ve had lots of times where I play a wrong note or what I perceive to be a wrong note, and I’m sort of searching for something and might play a weird half-step [note], and the whole band within that instant turns on a dime and follows that note. It’s a beautiful thing. But it almost took me sort of playing the wrong note to realize how dialed in we are as a unit.”

Though the new album deals in retrospection, the group continues moving forward. Greensky Bluegrass just extended its current tour into 2026, and Beck notes the group intends to go into the studio early next year, saying, “We’ve got tons of material for the next record.”

Though Greensky Bluegrass has built its reputation on live shows, Beck says it is the songwriting that will ultimately be the band’s most enduring creative asset.

“The success and longevity of a band comes from the songwriting. That’s why I joined this band 17, 18 years ago — the songs were f—king killer. In the digital age, it’s cool to think about the idea that anybody can find any music, anytime, and there will be some kid that goes back and discovers this band. Knowing that we’ve been successful in doing it our way is exciting.”