The Wooden Sky are a Canadian indie rock band based in Toronto, Ontario. They formed in 2003 as Friday Morning's Regret, but changed their name in 2007. In 2014 the band left their former record label to start their own Chelsea Records, an artist driven label that at present has released only the bands latest effort 'Let's Be Ready'.

The band originated after lead singer Gavin Gardiner wrote songs for a school project while attending Ryerson University. He formed the band with bassist Andrew Wyatt and drummer Chris Cocca, who has left the band. Their debut album, released in 2007, is When Lost at Sea. Band members now include Gardiner (vocals, guitars, harmonica), Wyatt (bass, vocals), Simon Walker (piano, vocals, guitar) and Andrew Kekewich (percussion).The band is frequently joined by Anissa Hart (Ohbijou, Kite Hill, The Rural Alberta Advantage) (cello), Mika Posen (Forest City Lovers, Timber Timbre) (violin, viola), and Edwin Huizinga (The Mars Volta) (violin).