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Some of it depends on what era of Star Trek you like, and what type of stories you like.

For instance - do you like The Original Series (TOS), The Next Generation (TNG), etc, or are you more interested in reading about new adventures in the Trek universe that don't involve the crews of the TV/movie series. The good part about the non-show oriented books is, there's very little chance of them being declaired non-cannon - you just know the setting/universe without being stuck with the problem of potential future shows/movies changing what you've read.

I understand Vanguard (which is only 2 or 3 books in) is a good series set in the TOS timeframe, but with separate characters (though the potential for guest appearances exists). New Frontier is much the same in the Next Generation time-frame.

Deep Space Nine relaunched with essentially an 8th season, which I can vouch was excellent reading at least up through Unity. Voyager had 4 relaunch books of lesser quality (taking place after the finale). Titan picks up Rikers new ship after Nemesis... but in most of these cases you're always running the risk of a future TV/movie plot changing what's come before.

Enterprise has less of that risk, despite Nom's love of the series, there's very little likelyhood of it being revisited outside of the novels.

If you like particular species of Star Trek, there are books and series that focus on them as well. There's a series of Klingon books put out by Keith DeCandido which take place in the Next Gen era.

There are also a number of Lost Era type books - filling in the gaps of Starfleet history (events mentioned in TV shows that took place in between series). Some of these feature TOS characters after their time on the Enterprise, some feature Captain Pike of the Enterprise, some a young Picard.

My focus is much more on TNG, as that's really my favorite, and I can certainly give you some great novels from that line.

Imzadi - one of my all time favorite books ever (not just Trek), while it is somewhat non-cannon after the episode that introduced Tom Riker, it still mostly works as a tale of how Deanna and Riker first got together.

Q Squared - most people think of this as Peter David's greatest Trek novel, again, it doesn't really step out of cannon

Dark Mirror - TNG crew revisits the Mirror universe from TOS episode, a great Deanna novel

Mosaic - A fantastic Voyager novel giving Janeway's history.

Probe - I enjoyed this follow up to Star Trek IV (though the author feels it's a bastardized version of her original novel) - it follows the Probe into Romulan space where Kirk and crew work together with the Romulans - very similar to Trek VI in some ways.

The Lives of Dax is a good way to start the DS9 relaunch if that interests you - it gives a tour of the lives of Dax (back through TOS timeframe) as it links up with many famous Trek characters.

I also understand that Federation is a great novel (though again, somewhat out of sync with cannon after First Contact) - which was a crossover between TNG and TOS. Crossover also had the TOS characters who live in TNG era on some kind of adventure, which I understand many like.

I've heard good things about the Kahn trilogy (giving his history up to his appearance in TOS, and maybe inbetween the TV show and the ST II).

If you like the Romulans (and TOS) I understand Diane Duane's Rihannsu books are great (and sort of fit in continuity as an offshoot of the Romulans).

And then there's a whole bunch of Short Story compilations - there's at least one per era (TOS is called Constellations, TNG is The Sky's the Limit, Voyager is Distant Shores).

Basically, there's something for everyone. I think you're always safest going into books about the history of a character, because they're the least likely to be covered in a future show/movie, and you often get guest appearances by other characters.

If you'd like a little more guidance, let me know if any of the above interests you and I'll try to make more recommendations.

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I'm a fan of Kirk, Piccard, Spock, McCoy and Sarek, though they may simply be those I have most exposure to.

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I wrote a huge response and lost all of it - so now I'm just going to give you the books I had recommended.

Q-Squared (picard)
Crossover (picard, spock, McCoy)
The Ashes of Eden (kirk - yes, it's a shatner novel, but it's generally accepted as fitting into continuity)
Sarek (Spock, Sarek)
Vulcan's Forge, Vulcan's Heart (Spock gets married, in-cannon)
Vulcan's Soul trilogy (spock in next gen era, plus flashbacks to the history of the Vulcans/Romulans)
Crucible trilogy (kirk, spock, mccoy during the original series)
Errand of Fury (2 books? may still be a book 3 coming - kirk and crew face war with the Klingons)
In the Name of Honor (kirk, klingons, set between movies 5 and 6)

If you're looking for books most likely to be a part of the cannon, look at the most recent novels (last 5 years or so) - that's when the editors of Trek lit decided it was important and the books started to become about filling in history (and so they're more likely to 'fit') and less about stand alone one shot novels that don't have any real effect. Most of what's above fits into that category of books.

Timeline is less important in Trek - with so many authors and stand alone novels set in between series episodes, it's much more about reading what you're interested in.