Over the next few years, Old Habits would gain momentum playing in small bars, and occasional parties. In 2007, they recorded their first self-titled album at The Rubberroom in Chapel Hill, NC.
Eventually drums were added to the line up, and the band moved from old-school bluegrass to their current sound – a mixture of Americana, Country and Southern Roots music. Evans Nicholson joined the group on drums in 2010.