In Oblivion, i was FASCINATED, with figuring out ways to get out of the cities, just to explore what seemed like a dead wasteland.
As a matter of fact, I think i successfully hopped the boundaries to every city in the game.

Well, today, I decided to try to get out of solitude, past the boundaries.
And I did it...

On accident by falling through a segment of a rooftop to beneath the city.

Have any of you attempted/succeeded at escaping city boundaries?

As dead as the world is, its still cool to see a less developed version of the land of skyrim ^-^