The group was initially formed as a casual collaboration between Freed, Govrik, and Gorman. The three had met together to jam on multiple occasions, constantly cycling a fourth musician. Trigger Hippy made its live debut on February 2, 2009, at the Cox Capitol Theatre in Macon, Georgia with Herring filling out the lineup. Due to Herring's tour commitment to Widespread Panic, the group recruited Greene and Osborne. The band toured the south of the US in the summer of 2011, playing shows in Atlanta, Birmingham, Nashville, Memphis, and Chattanooga; performing both original and cover material.
After playing shows throughout California, the group spent January 2012 at Mission Bells Recording Studio in San Francisco recording tracks for their debut album. In March 2012 it was announced that, after finishing these recordings, Freed had left the band. In his place, the band brought in Will Kimbrough, who was then replaced in August 2012 by Bukovac.
Trigger Hippy released their first EP on Record Store Day's Back to Black Friday on November 29, 2013. Trigger Hippy performed at The Peach Music Festival in Scranton, PA in both 2012 and 2014.
In May 2015, Trigger Hippy announced that Tom Bukovac had "left the band to pursue other opportunities". Guthrie Trapp replaced Bukovac for the remainder of the 2015 summer tour. On July 25, 2015, Jackie Greene announced via Facebook that he was immediately leaving the band to focus on his new solo album. Trigger Hippy confirmed on July 27, 2015 that they would continue on without Jackie and play the remaining August 22nd tour date.