Wouldn't it be awesome if Bethesda put in merchants, hunters, familys, groups of warriors and such walking on the roads between cities. Maybe they'll get attacked by bandits or wolves, or maybe you could rob a trade caravan? Or, if you're in a good mood, just tag along and see where they're going? Maybe a group of warriors are on their way to take down a giant or clear out a bandit camp? Maybe you can save a faily from a pack of wolves? It would work great along with the new conversation system, and it would make the world a whole lot livelier. In Oblivion and Morrowind, I always feel alone when I'm traveling by the road, and I often turn to quicktraveling. This would make it much more exciting to travel the slow way. In RDR, it was always exciting when you ride between towns, because you know that you might stumble upon something awesome, and you didn't feel like you were playing a whole new game every time you entered a new town. Why not implement this into Skyrim?

Please reply if there is something that would make this hard to implement into the game.

Already confirmed to be in. Eurogamer attendees saw a Dunmer making a pilgrimage to Windhelm, NPC hunters, Stormcloak soldiers escorting a prisoner, Necromancer's worshipping at Altars...

Yes

This has been confirmed awhile back!

Does anyone know to what extent?

Did you see my post?

Yea
I'm just wondering if this is going to happen regularily, or if the stormcloaks and the pilgrim were just the beginning of a quest