1. Turn off the HUD (Move Slider to the left), Crosshair, Floating Markers, all Auto-Saving, and Music. Set Difficulty to Master.
2. You may only have an animal follower, no regular followers. No Exploited armor or weapons. No going to inventory,map or favorites menu, meaning you must choose the one or two weapons and shout you will be using before starting challenge. Also make the veiw distance low and make it night time. No horses or dragon riding or Clear Skies shout. No inventory means no potions, however you are allowed to eat food. FInally, no swimming across medium-large bodies of water. You must go around rivers and lakes.
3. Go to the in-game map and shut your eyes (So you can't see the map), move the mouse/controller around the map randomly and select a select a spot (wait till you hear a click so you know it's a real location). Fast Travel there (Still should have your eyes shut).
4.You can open your eyes now. You should be at some random spot on the map. The challenge is you must make your way to city (major city). If you happen be at a city then just restart the map process and you will eventually be somewhere random again.
Heres my experience from when I tried it:
I ended up somewhere north of the map as it was very snowy and foggy. A giant wrecked ship was right in front of me. I had no clue where I was, not a town or city in sight. I started to head up the mountain and came across a humble Khajiit Caravan, who I decided to stick around with as they were heading to some city and had some warriors with them to help protect me. While on route, a vampire clan attacked from out of nowhere. I aimed to shoot one of the vampires with my bow but I struck one of the Caravan traders instead. All the traders went after me and a vampire took down one of them. In the end there was one of the traders left and all the vampires dead.
The Khajiit that remained was eager for revenge. I jumped behind and rock and tried to hide from her. I managed to keep quiet and the lonely Caravan member continued her quest. In the distance I spotted a swamp which could only mean that Morthal/Solitude was near by. I crossed the swamp and finally arrived at the arc that supported Solitude. I crossed the dragon bridge and made my way up to Solitude. Challenge Complete. Was very fun.
So in the discussion below, tell me how I can improve the challenge and your experience in the challenge. Try It!