IIRC, the quest involves not wearing any armor and staying outside for 2 days and 2 nights. The technicalities to this mean:
1) No armor = Equipping nothing at all...no boots, no rings, no hats/helmets, no bracelets, etc.
2) Outside = Entering a town resets the quest...you would have to start the two days again from the beginning.
As for time, it seems to go faster if you are moving. The last good trick I heard involving this was to aim your chars at the town wall, put something on your right-mouse button to hold it, and go down to the bar for a half hour. Or you could just go fill in the blanks in your map. It took me over 2 hours walking/running/riding to cover all of the Shire. I suspect it would take roughly the same amount of time to cover similar large, open areas in each of the main map sections.
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