Hitching in Calabria is generally not too hard, and also undertaken by some locals, although mostly for short distances. As the region has quite a poor public transport system, people are sympathetic.
There is one main motorway in Calabria, the ominous where numerous road works have been going on for over 30 years. While the runs along the Western part of Calabria (Tyrrhenian Sea), the Statale SS106 runs along the Eastern side (Ionian sea), and is said to be one of the most dangerous i.e. accident-prone roads in Italy.
As in many other regions of Italy, there may be people waiting on the roads (including the busy Statale) for other purposes, e.g. sex-workers. If you do not want to be mistaken, carrying a sign with your destination makes it quite clear.
You can easily hitchhike in via the , but some of its service stations, especially in the mountainous regions, may be quite deserted. For hitching onto the Ferry into Sicily, see Sicily#Hitchhiking In
Other useful info
There are numerous deserted villages, country side houses and sheds all throughout Calabria, and many old town centres are half empty. Therefore it shouldn't be difficult to find shelter for the night. Make sure though that they are uninhabited and not used for some other purposes!!!
If you ever do have to take a bus (pullman), it shouldn't cost too much, check the IAS autolinee site. http://www.iasautolinee.com/cms/index.php