[7] Originally from the small town of Yarmouth, Nova Scotia, members Paul Murphy and Tim d'Eon had known each other through their previous progressive rock band, Kary, which they formed in the mid-1990s, while still in high school, with drummer Mark d'Eon and bassist Jesse Luke.

[10] They released two albums through Dependent Music, a label and artist collective formed in Yarmouth, Nova Scotia in 1994.

[6] Wintersleep was selected as one of the opening acts by Paul McCartney for his concert at Halifax Common on July 11, 2009.

[11] That year, the band toured in support of Welcome to the Night Sky and also began writing their next record, New Inheritors, which came out on May 17 in Europe and May 18 in North America.

[citation needed] In 2011, the song appeared on the TV series Being Human and was also used in the background of a Molson Canadian commercial, advertising the "Red Leaf Project".

[citation needed] In 2013, "Weighty Ghost" became the theme music of the Canadian Broadcasting Corporation television crime drama Cracked.

[21] On Valentine's Day 2018, Wintersleep announced that their first three albums would be reissued on vinyl, with a bonus 7" single including previously unreleased tracks.

[24] The album release was supported by a national tour, from March 20 to May 3, 2019,[24] with some but not all dates featuring Partner as the opening act.

[citation needed] Wintersleep was joined by Montreal band Caveboy as the opening act at four Ontario tour dates.