Okay, Gary Whitta has mentioned that Telltale will most likely release something related to the Walking Dead before season 2 is out. I know we don't have any solid information beyond that and it might be too early to even speculate on it, but I'd figured I would give it a try. My thoughts are that Telltale might release an episode or two that might focus on certain characters from the series during the same exact timeframe of three months and what exactly happened to them during that time period.
It would interesting to have a DLC that focused on Crawford for example when it was a functional society. Perhaps play as a group of Crawford residents that begin to rebel against Oberson, who would be the main villain, and have Molly appear as a cameo appearance (or a playable character). Rough idea, but I think that could be done incredibly well and further peel away layers of the story, perhaps even reveal that Crawford actually murdered Clem's parents during their raids on Savannah or something to that extent.
Another interesting take I think would be playing as the Stranger for an episode and witness firsthand his account and even show what he truly had to do to stay alive. Playing as the main antagonist is something Dead Island did and I thought it was a really interesting concept, even though I really did not like the game in general beyond the story for that particular DLC.
There are so many directions this could take; Clem's parents, Vernon's group (before and after they stole the boat) and many others. Telltale may not be doing something like this, but if they were to do an episode or two that illustrated the events taking place at the same time in the eyes of other characters, it would be a really interesting way to compliment the story told thus far, and even contain some nice foreshadows to get fans ready for the next season.