Hellman first mentioned his dream of holding a festival for bluegrass music in the park to Jonathan Nelson in 2001. Nelson had worked for
Bill Graham Presents, and introduced Hellman to booking agent and executive producer Dawn Holliday, and production manager Sheri Sternberg at a lunch. Holliday and Sternberg agreed to help and would continue to produce the festival, respectively, each year thereafter. From the start, Hellman most wanted
Hazel Dickens to perform at the festival but Dickens, who was known for political songs about workers' strikes, was wary of performing because of Hellman's wealth and background. She later agreed, and went on to perform at the festival every year from 2001 until her death in April 2011. Hellman did not complain, and "Hardly" was eventually added to the name of the festival in 2004. Additionally, HSB worked with
Artist Relief to administer $1 million in relief aid to musicians. Annual in-person festivals in
Hellman Hollow resumed after the pandemic. ==Performing artists==