Derrick J Freeman spends 540 days in jail over the course of one year in Keene, New Hampshire, for offenses that amount to dancing, smoking cannabis, riding a bike, and showing up in court. The film follows his move from Philadelphia's gayborhood in 2011 to Keene's libertarian enclave, nicknamed 'The Shire,' after Stefan Molyneux, Ayn Rand, and Ludwig von Mises reshape his politics. Before the move, Freeman had spent five years on a crisis helpline and raised funds for Greenpeace and the ACLU. In Keene he becomes a co-host on the syndicated radio show Free Talk Live, runs Fr33 Agents Radio News, organizes 'Live Free Or Dance' street parties, and joins Cop-Block actions confronting police. The year closes with a fresh arrest and a 60-day sentence. Footage tracks his outreach, videography, and blogging as he practices agorism, building black-market and gray-market alternatives to state control. The film treats each arrest as a test case for what counts as a victimless crime.