Made it to Level 100. Still looking for new locations on the map. Do I start a new character? Any new Xbox 360 games worth playing?

I usually start a new character after I have done most (or all of the quests) in the game and visited most (or all of the locations). At that point I'm usually between level 85 and 95. It's up to you though what you want to do.

I could be wrong, but now that the next generation console (XboxOne) is out, the number of really "good" games are going to be limited for the Xbox 360. You can always check this web site: http://www.xbox.com/en-US/xbox-360/games out too if you are interested in the newer releases. That being said, the remastered version of the original Fable came out a while back. I think I'll refrain from mentioning any others, because this forum is meant to be for discussion of Skyrim.

The great thing about TES games is you make the choice to play any character however long you wish. This is one of the reasons behind me loving this series the way I do.