Helms is also in a bluegrass band called The Lonesome Trio with his friends Ian Riggs and Jacob Tilove. They formed the band when they were at Oberlin College and still get together to play a few shows every year. They recorded an eponymous album in summer 2013 shortly after appearing on the Bluegrass Situation stage at the Bonnaroo festival, which Helms curated. Helms is a self-confessed "bluegrass nerd" and founded the annual LA Bluegrass Situation festival. Helms plays banjo, guitar and piano. He and Amy Reitnouer co-founded a music blog also titled "The Bluegrass Situation". It summarizes its mission as "Creating and covering content across every level of the international scene, ranging from timeless traditional bluegrass, blues, and old-time to contemporary singer/songwriter, Americana, folk, and everything rootsy beyond and in between." On April 22, 2020, "The Bluegrass Situation" debuted "The Whiskey Sour Happy Hour," a weekly music and comedy program befitting the MusiCares COVID-19 Relief Fund and Direct Relief.