Note: I recently updated this post and republished it as a new post. You can find the updated version by clicking here.
I love Fables, Jack of Fables, and all of the brilliant spin-offs by Bill Willingham and his team published by Vertigo. I had a Twitter conversation earlier that brought to mind how complicated the series can be if you are just starting out. I am all caught up and tend to read the books as they are released, but when you haven't read even one of them it can be a bit overwhelming, right? And, your first instinct might be just read all of the Fables and then all of the Jack of Fables and so on. I am here to point you in a direction that might lead to a more rewarding experience of the world.
F= Fables and J = Jack of Fables. It should be clear, but just in case.
It starts off easily enough:
F - Volume 2: Animal Farm (Issues 6-10)
F - Volume 3: Storybook Love (Issues 11-18)
F - Volume 4: March of the Wooden Soldiers (Issues 19-21; 23-27)
F - Volume 5: The Mean Seasons (Issues 22; 28-33)
F - Volume 6: Homelands (Issues 34-41)
NOTE: Congrats, you are now safe to start Jack of Fables. The events in this book pick-up after issues 34 and 35 of Fables contained in Homelands. You do not have to start now, but if you want to it is now safe. It didn't actually release until after Volume 8 of Fables.
F - Volume 7: Arabian Nights (and Days) (Issues 42-27)
F - Volume 8: Wolves (Issues 48-51)
STOP!! If you haven't all ready, you should read 1001 Nights of Snowfall. I did not, but it ties into Volume 9 of Fables. (I don't think you lack if you just read it whenever. It is technically a prequel.)
F - Volume 9: Sons of Empire (Issues 52-59)
F - Volume 10: The Good Prince (Issues 60-69)
F - Volume 11: War and Pieces (Issues 70-75)
F - Volume 12: The Dark Ages (Issues 76-82)
STOP!! You are now on a Fables vacation. In order to read Volume 13 you have to read Jack of Fables because this is a Crossover edition.
J - Volume 1: The (Nearly) Great Escape (Issues 1-5)
J - Volume 2: Jack of Hearts (Issues 6-11)
J - Volume 3: The Bad Prince (Issues 12-16)
J - Volume 4: Americana (Issues 17-21)
J - Volume 5: Turning Pages (Issues 22-27)
J - Volume 6: The Big Book of War (Issues 28-32)
STOP!! It is now time for a Jack of Fables vacation. Sort of. When released as individual issues Volume 13 actually contains Fables, Jack of Fables, and The Literals. When they released it as a trade paperback they put everything together and called it Fables.
F - Volume 13: The Great Fables Crossover (Fables: Issues 83-85; Jack of Fables: Issues 33-35; The Literals: Issues 1-3)
Note: Now, you can do what you want for the rest of the Fables and Jack of Fables. A suggested order is such (this is how they were released and I read them):
J - Volume 7: The New Adventures of Jack and Jack (Issues 36-40)
F - Volume 14: Witches (Issues 86-93)
J - Volume 8: The Fulminate Blade (Issues 41-45)
F - Volume 15: Rose Red (Issues 94-100)
J - Volume 9: The End (Issues 46-50) - This concludes Jack of Fables.
F - Volume 16: Super Team (Issues 101-107)
F - Volume 17: Inherit the Wind (Issues 108-113)
F - Volume 18: Cubs in Toyland (Issues 114-123)
There is also the standalone comic Werewolves of the Heartland that was finally released at the end of last year. The comic is a chance to see Bigby all by himself. It is technically a good introduction to the series; but if you are worried about any possible spoilers it was originally set to be released around the same time as Super Team and follows events from that comic.
Then, there is Cinderella: From Fabletown with Love (Issues 1-6) and Cinderella: Fables are Forever (Issues 1-6). From Fabletown with Love does its own thing, so no real worries for spoilers. Fables are Forever, though, does talk about events from later in the series. If you want to avoid possible spoilers do not read it until after Fables: Volume 13. Also, the two collections are entirely unrelated. There is no need to read one right after the other.
The newest addition to the Fables family is the comic book series Fairest. Fairest - Volume 1: Wide Awake was released in November of last year. This comic book series is a good starting point if you are overwhelmed with the series overall. If you are worried about spoilers, though, you should wait until the huge story arch is completed in Volume 13. It is not so much huge spoilers as making you wonder how things got to that point; so it might actually make you more eager to check out the earlier comics. The sequel, Fairest - Volume 2: Hidden Kingdom, will be released in July.
Lastly, there is the novel Peter & Max. This is an original novel that also can be read as an introduction to the series. I don't remember any spoilers for the series, so I wouldn't worry about a reading order. If you are in the mood for a Fables novel instead of graphic novel, pick this one up!
One thing I left out of this post originally was that the comic book series has been collected into Deluxe Editions. I have been buying them as trades, so I don't actually have the hardcover editions, but I thought I would also include them at the bottom here if you are looking for an easier way to collect the series:
Volume 1: Fables 1-10
Volume 2: Fables 11-18
Volume 3: Fables 19-27
Volume 4: Fables 28-33 (1001 Nights of Snowfall)
Volume 5: Fables 34-45
Volume 6: Fables 46-51 (Up-coming)