This discussion may contain spoilers!
At Comic-Con 2013, Dan Connors, the CEO and Executive Producer of Telltale Games stated "We're hard at work and it's certainly something we're looking at this fall. So Episode 1 is starting to really to take shape. So we're working on it, we don't have have an exact date right now but it's happening.It was confirmed in an interview with Nick Herman and Dennis Lenart about The Wolf Among Us that Season 2 will be released around the same time as The Wolf Among Us, which was released on October 11th. Dennis Lenart is also the director of the first episode of this season.
It is said that some of the characters who were first introduced in the "400 Days" DLC are anticipated to appear in this season.