The books in the Heroes of the Lance period are plagued with various stories going back and forth between the period of the Chronicles and Legend Series.
We suggest going through the books within this period that interests you before hitting the 5th Age. The world really takes a whole new turn in the 5th Age. There is no particular order between these series so we have tried to categorize them by "subjects".
Stories About the Heroes
There are many books out there that concentrate on the heroes that you have read about in the Chronicles and Legends series. Most of these books travel back before the Chronicles and detail the adventures of the heroes and how they met.
Many people consider these books not to be the "true" stories of the companions, but on the whole, most of them are entertaining reads.
The Meeting Sixtet
Go way back and explore the youth of the companions. This series will take you back to the heroes youthful days.
The Preludes discusses the journeys of the companions prior to the War of the Lance (the 5 years before Chronicles).
Darkness and Light
Riverwind, The Plainsman
Flint, The King
Tanis, The Shadow Years