Introduction: Rehoboth, the name of my hometown in southern Massachusetts, comes from the Hebrew work for “crossroads.” Indeed there’s not much in this rural town besides Route 44 and Route 118, with smatterings of horse farms and single-family homes. These two blue highways intersect at the town’s only stoplight. A sign stands at this intersection at the center of town, in front of the Cumberland Farms convenience store, across the street from the new Dunkin Donuts. It reads: Rehoboth, MA: Birthplace of Public Education in North America. I’m a product of these schools, but in this thesis I explore the road not often traveled in education: unschooling, a type of homeschooling with unstructured, child-directed learning. Through an examination of the attitudes, beliefs and practices related to media and technology in the unschooling subculture, I come to a definition of participatory media.