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. 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 signed with Flicker Records, which is owned by members of Audio Adrenaline, and changed their name to The Swift. They released their self-titled album later that year.

After a debut that brought them moderate success, The Swift then released their second album entitled Today. Early 2004 brought about a line-up change. Guitarist Chris Byers decided to leave the band and was replaced by Justin Sharbono (formerly of Superchic[k] fame).

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 of 2006. He was replaced by Guy Lemon. The band released an independent worship EP before leaving Flicker Records to sign with Michael W. Smith's Rocket Town Records. A new album is scheduled for release in October of 2006.