The Final Reflection(TOS) by John M. Ford
- The
very best star trek book there is. Totally at odds with any trek from TNG onwards since it was written in the eighties. A story set in the early days of the federation shortly after they had met the klingons. It's a fantastic story of their early contact from the point of view of a klingon.
Where Sea Meets Sky(TOS) by Jerry Oltion
- A very enjoyable cap'n pike exploration tale with a nautical feel. Was part of the "captains table" series, but doesn't require reading any of them.
Federation(TOS,TNG), by Garfield and Judith Reeves-Stevens.
- It spans three eras and focuses on Zefram Cochrane(based on his TOS appearance, First Contact hadn't come out at this point). It feels like the kind of epic "The Motion Picture" tried and failed to be.
Yesterday's Son/Time for Yesterday(TOS) by Ann C Crispin
- A couple of great books that focus on spock and a rather surprising relationship.
The Wounded Sky(TOS) by Diane Duane
- Super exploration, crazy concepts and, as is almost standard for Duane, a brilliant alien species.
Spock's World(TOS) by Diane Duane
- Deals with Vulcan -its past and what they think it's future should be. Includes an absolutely barnstorming McCoy speech. Would be nice to have read The Wounded Sky first.
Doctor's Orders(TOS) by Diane Duane
- Kirk puts McCoy in the captains chair, and things spiral out of control from there. Some great aliens to boot.
Memory Prime(TOS) by Garfield and Judith Reeves-Stevens
- Great take on artificial intelligence and conspiracies.
First Frontier(TOS) by Diane Carey
- Time travel, alternate timelines & Kirk fightn' round the world.
The "Errand" series(TOS) by Kevin Ryan
-It's made up of two trilogies, Errand of Vengeance and Errand of Fury, which tell the story of the TOS era conflict between the federation and the klingons, split into basically four viewpoints - a starfleet command officer on earth, a security officer aboard the enterprise who is a klingon infiltrator, an officer aboard a klingon warship, and finally kirk.
One of the best flowing, and most satisfying trek stories I've read.
Book order if you're interested:
The Edge of the Sword
Killing Blow
River of Blood
Seeds of Rage
Demands of Honor
Sacrifices of War
Masks(TNG) by John Vornholt
- Away mission on a human colony which eschewed modern technology and cut itself off from earth and ended up going back to a sort of feudal system - but with an interesting twist guided by some of the original colonists. The thing I like most about this book is how well the world and its people is put together. Characterisation(mostly Picard) can be a bit off since this was a very early novel, but it does end up kinda feeling like movie picard.
Q-Squared(TNG) by Peter David
- An incredibly intelligently written book that weaves together alternate dimensions into a very interesting story.
Strike Zone(TNG) by Peter David
- flits between hilarity and some pretty dark scenarios with great ease as a race antagonistic to the klingons chance upon superweapons and figure the klingons would make for great targets. Wesley is used well(much better then the tv writers normally managed).
Imzadi(TNG) by Peter David
- Story of the first meeting between Riker & Troi, amongst other things.
A Rock and a Hard Place(TNG) by Peter David
- Delves a bit into Riker's past as he goes on leave to help a friend. The other half of the story is his replacement, who is the star of this story. Don't want to go into him as that's the best part of the book.
Dark Mirror(TNG) by Diane Duane
- deals with the mirror universe, written before ds9 went back to it so expect gaping discontinuity - as with Federation, I enjoyed the authors version a lot more then what would later transpire.
Intellivore(TNG) by Diane Duane
- feels like a mystery where the crew are slowly trying to find a creeping horror. the tension in this book amps up very well through to the conclusion.
Possession(TNG) by J.M. Dillard and Kathleen O'malley
- a sequel to a pretty poor TOS book which thankfully isn't necessary reading(I read this one first and never even realised there was a prequel). Great tension as the pressure builds throughout.
Q Continuum trilogy(TNG) by Greg Cox
- fun trilogy with a lot of good q/picard interaction, plus a great explanation for a long standing trek mystery
Diplomatic Implausibility(Klingons post TNG) By Keith R A Decandido
- Worf tries out his diplomatic muscles for the first time. If you like the Klingon crew (I did), their story continues with the same author in the following books:
A Good Day to Die
Honor Bound
Enemy Territory
A Burning House
Objective: Bajor(DS9) by John Peel
- Really fun book, has aliens with a rather interesting fundamental problem encroaching on bajoran space because of how that problem makes them view certain aspects of most cultures. Hard to explain without spoiling it.
The 34th rule(DS9) by David R George & Armin Shimmerman
- Brilliant book focusing on Quark and how Ferengi tick, a grand Machiavellian scheme he gets involved with and a superb payoff.
A Stitch in Time(DS9) by Andrew J Robinson
- Pretty much the same as above but for Garak. Great look at his youth and at post-ds9 cardassia
The Millennium trilogy(DS9) by Judith and Garfield Reeves-Stevens
-Three great books about a possible future with an epic "everything on the line" feel
If you end up liking Peter David's style, I'd also recommend reading his "Star Trek : New Frontier" series, which has a captain that feels very much like the guest character from "A Rock and a Hard Place", below is the reading order:
House of Cards
Into the Void
The Two-Front War
End Game
Martyr
Fire on High
Captain's Table: Once Burned - Was part of the "captains table" series, but doesn't require reading any of them.
Double Helix: Double or Nothing - Was part of the "Double Helix" series, but doesn't require reading any of them.
Double Time (this is a graphic novel - not absolutely required reading, but pretty fun and does get referenced once or twice)
The Quiet Place
Dark Allies
Excalibur #1: Requiem
Excalibur #2: Renaissance
Excalibur #3: Restoration
Gateways: Cold Wars
-Was part of the "Gateways" series, but doesn't require reading any of them, except maybe...
Gateways Book 7: What Lay Beyond
- "Gateways" was a series of six books that all ended on a cliffhanger (cold wars above was the New Frontier entry, you don't need to read any of the others), and book 7 is a series of short stories that completes each story. I always thought this a bit of a scammy move personally as you're buying stories you very well may not want. The short story "Death After Life" is the "Cold Wars" conclusion.
Being Human
Gods Above
Stone and Anvil
There are more books after stone & anvil but imo the quality is quite a bit lower. Still enjoyable in parts though.