Does the road wind up-hill all the way? Yea, to the very end. (1-2)
This passage emphasizes that the journey upward is not always an easy one. Concerns, doubts, and distractions can get in the way of one's spiritual quest, and a great deal of perseverance becomes necessary to reach the final destination.
Will the day's journey take the whole-long day? (3)
And, if so, can we at least stop somewhere yummy for lunch? Only after putting in a full day's work, though.
May not the darkness hide it from my face? You cannot miss that inn. (7-8)
You can almost imagine Speaker #1 as a runner in a race with all these questions about the track ahead and Speaker #2 as a coach, tirelessly running alongside him the whole way and providing the answers. In some ways, Speaker #2 seems almost more determined to get Speaker #1 to the finish than Speaker #1 seems determined to get there.