GTG:
Primary information sources would include autobiographies written by law enforcement officials (for example, The Dry and Lawless Years about the Chicago area), those written by "reformed" bootleggers, and newspaper accounts from the era you are researching.
I'm sure the historical society journals have run plenty of solid articles about the time and place - and those generally offer excellent bibliographies.
I'm also sure there are quite a few histories written about famous bootleggers and their vessels, both books and magazine articles.
Maps from that period would also be helpful. It only makes sense that bootleggers would avoid the main roads with checkpoints in favor of dirt tracks and other, lesser-used, venues.
Good luck to all,
~The Old Bookaroo