Why does the list of locations the wagon will take me to change?

On one of my characters, the guy in the wagon at Whiterun will take me to almost any city in Skyrim.

On my slightly newer character, he only lets me go to four cities - Markarth, Riften, Solitude and Windhelm.

My first character has all those plus places like Morthal, Winterhold, and Falkreath.

What's the reason behind this? It's not based on which cities I've visited (as I've only visited Riften out of the four on my second character).

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3 Answers

Locations only show up if you have enough gold to travel to them, it is likely that your newer character did not have sufficiant gold to travel along the more expensive routes.

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I just had the same issue except only the 20 gold options were available. I traveled to them all and back to whiterun and that seemed to fix the problem.

Try to scroll down. May be the issue