So, a couple theories about Long Road Ahead:
Kenny, Katjaa, Duck and Ben will take the RV, splitting the group in two. Lee, Clem, Lilly and Doug/Carley will then go to Woodbury, where Lilly stays. The thing that i'm doubting about is that Lee and Clem is seen with Ben and Duck on the train, which means that the two groups, at some point, will meet.
Kenny's group might have hid at the train station, where they meet the three new survivors. Lee and Clem then leaves Lilly and Doug/Carley at Woodbury, and find the station. They then takes off.
But i don't know. I don't think that Doug would leave Lee. Carley maybe? I dunno. Gimme your theories.