TrekBBS user Thrawn constructed an intricate flow chart to help you navigate the many Star Trek novels by where they fit into the continuity of the Star Trek universe. The screenshot here is just a small corner of the huge chart.
Whether you're a fan of TNG, DS9, Voyager, or Enterprise the chart below will show how they spin off into New Frontier, Titan, Klingon Empire, or Vanguard, and crossover into Destiny, Typhon Pact, The Fall, Mirror Universe, and more; letting you chart your own path through the Trek-litverse. Once you've got to grips with the flow chart you might also find some of my lists a useful reference too.
The chart encourages a reader to start anywhere they like, as the novels themselves fill you in on what you need to know. However, the chart will help you to decide what to read next and how the stories fit with each other. There aren’t many novels included from the era of Kirk and Spock, just a few that were set after the movie era began. More reading suggestions can be found with the chart at the Trek Collective. -via Metafilter