The group started in the year 2002. During that time, the group consisted of Ruth Moody, Nicky Mehta and Cara Luft. The three started to sing together when the owner of guitar shop in Winnipeg called Sled Dog Music asked them to make a performance. The three eventually click and the owner scheduled a follow-up show which also became successful. The owner offered that they might go on tour and call themselves The Wailin' Jennys. In the year 2004, after the released of their full length debut album entitled 40 days, Cara Luft decided to leave the group and pursue a solo career. Cara Luft was replaced by Annabelle Chvostek.
The Wailin' Jennys EP: released in 2003 under Red House Records (American independent record label specializing in folk music based in St. Paul, Minnesota), produced by David Travers-Smith.
40 Days: Debut full-length albums of The Wailin’ Jennys, released on August 10, 2004 under Red House Records, produced by David Travers-Smith, title of the album came to the number of days it took to record and refine the album; the album won the Juno Award for best Roots & Traditional Album by a group in 2005.
Firecracker (The Wailin' Jennys): The Wailin' Jennys' latest album, released on June 6, 2006 under festival Distribution (a Canadian independent record label and music distributor, specializing in folk music and world music artists), reach number two spot in Billboard Bluegrass charts in 2006.