Does the road wind up-hill all the way?
Yes, to the very end.
Will the day's journey take the whole long day?
From morn to night, my friend.
But is there for the night a resting-place?
A roof for when the slow dark hours begin.
May not the darkness hide it from my face?
You cannot miss that inn.
Shall I meet other wayfarers at night?
Those who have gone before.
The ‘darkness’ might represent the problems encountered on this journey which generate despair, and therefore exclusion from salvation. In this case the questioner fears losing their way, maybe being tempted by sin, and missing the opportunity of heaven.
Up-hill