The Oddball Comedy and Curiosity Festival will include "two stages, street performers, vendors, psychics, freaks, tasty treats and more". Kristen Schaal, Hannibal Buress and Al Madrigal are also performing in the tour, which begins on 23 August in Austin, Texas.
Chappelle, 39, abruptly left the US in 2005, midway through production of the third season of his popular Comedy Central series, Chappelle's Show. He later told Time magazine that he had flown to South Africa to find "a quiet place", because he was overwhelmed by the show's success and the $50m deal he had signed with the channel.
He returned to the US shortly after and avoided the spotlight, with the exception of a few television appearances and those impromptu gigs. Chappelle twice appeared on the interview show Inside the Actors Studio. In one such appearance, he explained why he had left his immensely successful show.
In February, he made made a surprise appearance on stage with Chris Rock. They joked about going on tour.
"After next Tuesday, I'm free for like 11 years," Chappelle told Rock,