The Internet’s importance in promoting free and open communication has led to widespread crackdowns on its use in countries around the world. In this study, we investigate the relationship between national policies around freedom of speech and Internet topology in various countries. We combine techniques from network measurement and machine learning to identify features of Internet structure at the national level that are the best indicators of a country’s level of freedom. We find that IP density and path lengths to other countries are the best indicators of a country’s freedom. We also find that our methods predict the freedom category (Free/Partly Free/Not Free) of a country with 95% accuracy.