Initially known as Regeneration X, the band was formed as a youth/camp retreat band in 1998 by Britt Edwards, Jason Wiliams, and Danny Daughtridge. They soon changed their name to Puddleglum after the C.S. Lewis character in The Chronicles Of Narnia. Chris Byers replaced Jason Williams and Phillip Wall was brought in as a lead guitarist. Trae Drose became the permanent drummer around the same time. Danny Daughtridge left and was replaced by Phil Sabella, who would later go on to form Oldmangrady with Lee Modlin and Joe Knowles. After Phil's departure, Mike Simons (formerly of Zaccheus Tree) joined as percussionist and vocalist. Phillip Wall left to attend seminary and the band continued as a four-piece. As the band began to tour, it gained popularity which fueled the need for original music and a record label.

In 2002, the group decided to sign on with Flicker Records and changed their name to The Swift. That same year the band released their self-titled album, which produced two top 10 Contemporary Christian hits: "Under The Sun" and "More Than Gold."

Early 2004 brought about a lineup change. Guitarist Chris Byers decided to leave the band and was replaced by high-powered guitarist Justin Sharbono (formerly of Superchic[k] fame). The Swift then released their second album, entitled Today.

After only seven months with the band, guitarist Sharbono left the band to pursue other interests. In order to fill the void, the band decided to reach back into their hometown and added guitarist Matt Wilder (also from Zaccheus Tree) to the roster in December 2004. Drummer Trae Drose announced his decision to leave the band in May 2006. He was replaced by Guy Lemon.

In 2006, the band broke with Flicker Records and signed with Rocketown Records and released a softer, more contemplative album, Singing Back To You. At the Life Conference in Orlando, Florida in 2007, the band announced they were ending their run.