The band formed in 2001 by former students at Winston Churchill High School and Mountain View High School in Eugene Oregon, the same place where Rock N Roll Soldiers and Tracy Bonham have started their music career, taking their name from a small insect, the caddisfly.

likened the band's sound to that of The Juliana Theory, calling the album "the perfect blend of thrash, mainstream rock, and textured prog all wrapped up in post-punk emo.

An EP, Four Seasons, was released in 2006, and a second album, Set Sail the Prairie, was issued in 2007, both on Hopeless sublabel Sub City Records.

Allmusic described Set Sail the Prairie as "big, rich, and texturally varied", but with "disjointed and haphazard" song structures.

[2] Drowned in Sound had a similarly mixed response to the album, noting, "Maybe the most irritating thing about this release is the potential constantly in sight just over the horizon, but never reached.

As Kaddisfly we may very well end up finishing horses galloping one day, but for now, I suppose the popular thing to say would be we are on a small hiatus.

On January 5, 2015, they updated their Facebook page with a tracklisting for the upcoming 2015 release of Horses Galloping on Sailboats.