Members (Sam, Don, Auyon, Harris, and David) met as undergraduates while attending Williams College in Williamstown, MA.
They released their debut full-length album, Pilot Machines, in 2012, which was recorded and co-produced by Nathaniel Kunkel (who has worked with Sting, Lyle Lovett, Graham Nash).
[3] Writing about Pilot Machines, David Fricke of Rolling Stone praises the band as having “a rich line in acoustic textures and chamber-rock dynamics.”[4] After Kapala's departure from the band in 2013, Darlingside moved toward a traditional bluegrass set-up (notable because they do not play bluegrass) with all four remaining musicians clustered around a single condenser microphone.
Following additional national tours translating their indie-rock songs into quartet arrangements, Darlingside released their second full-length album, Birds Say, in September 2015.
In 2022, Senft announced that he would no longer tour or perform live with the band, though he would continue contributing in his other roles including writing and recording.