The band was originally formed by singer Andy Maize, previously of Direktive 17, and lead guitarist Josh Finlayson, formerly of The Ramblers, as a duo called
West Montrose. The band later added rhythm guitarist and singer-songwriter
Peter Cash, drummer Wayne Stokes and bassist Ron Macey to their lineup after becoming regular performers at Acoustic Meltdown, a weekly concert series at
Toronto's
Spadina Hotel organized by Cash's brother, singer-songwriter
Andrew Cash. The expanded line up settled on the name Skydiggers, a name which Andrew Cash had previously considered for his own band. With
Restless, their most popular album, still unavailable in stores due to legal uncertainties around FRE's bankruptcy, they decided that their next studio project would be to assemble a new version of that album using old rehearsal recordings.
Still Restless: The Lost Tapes was released that year. In 2000, the band released the live album
There and Back Again, followed in 2003 by
Bittersweet Harmony. In 2006, they teamed up with
The Cash Brothers (former Skydigger Peter Cash and his brother Andrew) to release,
Skydiggers/Cash Brothers, an acoustic album. In 2008 they released
City of Sirens, followed by the compilation
The Truth About Us in 2009. The band returned in 2012 when they released
Northern Shore through MapleMusic Recordings. In 2013, the band released
No. 1 Northern, an album of
cover versions of songs by Canadian songwriters, including
Neil Young,
Gordon Lightfoot,
Ron Sexsmith,
Gene MacLellan,
Linda McRae,
Charlie Angus and Andrew Cash. They also released the album
She Comes Into The Room. In 2013, the band released the five-track EP
Angels for the holiday season. A year later, this was expanded to 11 songs and released as a full album. The band are currently signed to Latent Recordings. On January 1, 2017, Skydiggers were part of CBC's The Strombo Show's Hip 30, where Canadian bands covered songs from
The Tragically Hip to commemorate the Hip's 30th anniversary. The band covered the song "The Depression Suite: The Rock". 2017 also saw the release of the Skydiggers latest LP
Warmth of the Sun. The band is a member of the Canadian charity Artists Against Racism. ==Finlayson/Maize==