[2] Adam Young met Andy Johnson when they were both in elementary school and began making music.
[3] The group wrote parody songs and recorded them on a PC mic, as well as selling their CDs from their lockers.
[7] Between the release of The Basement EP and mid-2003, they played at several shows including Sunshine Festival, Bethel Church,[8] and Ironwood Springs.
Abandoning nearly every aspect of pop/punk, they began writing music influenced by Unwed Sailor,[3] and quickly released Selections for a Fallen Soldier.
[5] Throughout 2005 and 2006, they continued to play at shows and write music with an additional member, and long-time friend to the group, Michael DeMars.
[16] Young and Andy collaborated on a project via the internet, and released the EP, Beneath The Crystal Waves.
[17] In 2007, the band slowed down as Young's electronia project, Owl City, began to rise in popularity.
[24] Some songs from the album were written for Tony Johnson's then fiance Emily Jane, most notably the track, "Snowfall".
[25] The group described The Meadow as an album that, "follows its characters through long, toilsome journeys, optimistic summers days, and inevitable storms.
[5] On April 28, Windsor Airlift returned to its origin home of Owatonna, Minnesota for a homecoming concert, performing alongside Cabin of Love and Carinthia.
[5] They also played a show with Carinthia and Swimming With Dolphins at the Varsity Theater in Minneapolis, Minnesota in the neighborhood of Dinkytown.
[28] However, in September 2013, Windsor Airlift revealed that they were raising money to create physical CD formats of another album: Music.
[33] On April 6, 2014, the band released a small snippet to a track they were working on, via Instagram which later was revealed to be titled, "Beginnings".
[34] On August 10, Windsor Airlift re-released their second album, Moonfish Parachutist for free download via DropBox.
[35] On August 30, the group performed a show at the Vaudeville Mews in Des Moines, Iowa alongside Unwed Sailor.
[53] This, in turn, explains the multiple YouTube videos the band has posted of them throwing and wrecking old television sets and speakers.
[86] A good deal of the songs produced, centered around Waldorf College, the school that Andy and Anthony Johnson attended.
In 2007, Andy and Tony Johnson created a minor one-song project entitled Casey's Pizza.
In early 2012, Andy Johnson released a solo worship album entitled Love Songs.