Reason conducted an interview with Political scientists Jason Sorens (University at Buffalo) and William P Ruger (Texas State). How they measured which states were more or less free was through looking at everything from drug policy to civil union statutes to business regulations and tax rates. Essentially, they ranke each state across multiple dimensions (personal, social, and economic issues). A general sum of what they found:
At the top of the list are a lot of states where almost nobody lives and at the bottom are states where just about everybody lives.