During the events of the series. (298 A.C.)

Alright, so Robert Baratheon has already been King of Westeros for fifteen years.

Now that we have an idea of when this takes place, let us continue.

As you urge Aerion to take you down the eastern road, you wonder where you should head.

If you follow this road all the way to the end, you will enter the Vale and ultimately end up at the Bloody Gate. Once behind the Bloody Gate, your safety is all but guaranteed, and you could find work and shelter at the Eyrie, the ancestral home of House Arryn. However, first you need to venture through miles of dangerous terrain. The area between the crossroads and the Bloody Gate is crawling with many clans of wild men and unsavory beasts such as shadowcats. Furthermore, you have no way of knowing if the Knight of the Bloody Gate will allow you entrance. You would definitely be taking a gamble if you choose that path.

Another option is to only follow the eastern road until you reach the border between the Riverlands and the Vale. Once there, you can turn southeast, towards the Crownlands. From there, you have options aplenty.

Your two most promising prospects would be Dragonstone or King's Landing. The island stronghold where privacy is guaranteed, and the capital city, where work is in abundance.

So... where will you go?