RoSFest was founded by George Roldan and Tom Smith and made its debut in 2004 at the Colonial Theatre in Phoenixville, Pennsylvania. In 2007, it moved to the Keswick Theatre in Glenside, Pennsylvania where it remained for two years. In 2010, the festival moved to the Majestic Theater in Gettysburg, Pennsylvania where it had its longest residence of nine years. Finally, in 2019 the festival moved to its current location at the Sarasota Opera House in Sarasota, Florida.