Aged 16 Oram was signed to indie label Wellcraft Music Group and released her first country music single called, "More Than I Dreamed" which was her first top 50 hit. She later toured with a local agency called Performerz, which allowed her to sing in theatres, malls and festivals throughout Ontario. When 19 Oram joined her first real band, Big Catch. The band played the bar/club circuit and corporate events around Ontario for the better part of four years, performing a mix of country, top 40, rock, R’n B and retro. In 2007, Oram auditioned for the hit show Canadian Idol, earning a 6th place finish on the hit reality show. The next year, Oram signed her first major record deal with Open Road/Universal Music Canada and also appeared on reality TV series called, "The Tara Diaries" on CMT. CMT filmed a Christmas special she hosted, "The Night Before Christmas". In October 2008, Oram's first show as a signed artist was opening for her Idol, Marty Stuart in Halifax, Nova Scotia.
In 2009, CMT and YTV Oram appeared a celebrity judge on the TV series, "Karaoke Star Junior".
Oram received nominations for the 2009 East Coast Music Awards in the categories Female Solo Recording of the Year and Video of the Year, and won in the Country Recording of the Year award. She also received a CRMA (Canadian Radio Music Award) nomination as Best New Group/Solo Artist. On February 2, 2009 Oram was nominated for a Juno Award in the Country Recording of the Year category. Oram won the 2009 CCMA Rising Star award. She was also nominated for Rising Star, Female Artist of the Year and Video of the Year.