Over the course of a journey, the narrator asks her guide eight questions about the road ahead. The narrator asks if the roads are all up-hill and if the journey will take all day. The guide replies in the affirmative. Next, the narrator asks if there is a place to rest for the night and if the darkness will obscure said resting-place from their view. The guide assures the narrator that there is an inn and they will not be able to miss it. The narrator's fifth question is about which other travelers will be on the road. At the inn, the narrator asks if the other travelers would prefer for her to knock or call out. The guide tells the narrator that someone will open the door. Lastly, the narrator asks if there will be a bed for her. The guide tells her that there are beds for everyone.
The question and answer form is common in devotional writing, because it encourages the reader to contemplate his or her own response to the question. The guide addresses the narrator as “my friend," which is also what Christ called his disciples. The poem is comprised of four stanzas with four lines each, following the ABAB rhyme scheme. In this way, the rhyme scheme separates the traveler from the guide, and the simplicity alleviates the pressure of the difficult topic. The meter starts with a trochee and shifts into alternating iambic pentameter and trimeter. The pace is consistent, just like the narrator's steady up-hill climb.
The journey is the prominent symbol in this poem, and is open to a few different interpretations. The first interpretation is that the poem symbolizes the journey from birth to death. The darkening sky foreshadows the end of life, and the inn represents the final resting place. Considering Rossetti’s religious background, this final resting place could be interpreted as Heaven. The act of knocking on the door represents the Christian confession of sin and the need for forgiveness before admittance into Heaven. When describing this moment, Rossetti chooses to use a nearly verbatim quote from the Gospel of Matthew. Rossetti frames death as a form of respite after the tiring journey of life.
There is a slight possible variation on the interpretation that the road represents the journey of life. Already careworn, the weary traveler wonders if life grows easier as she grows older. However, the guide tells her that the road that remains is up-hill and arduous. This interpretation does not resolve the symbolism behind the inn. It is possible that the inn could represent death, which also provides an opportunity for rest at the end of the road.
A third reading seems less likely because of Rossetti’s religious views, but it is worth examining. This school of thought considers the journey to represent Christian purgatory. In this case, the inn would also represent Heaven, just like in the first interpretation. “Up-hill” is a classic example of Rossetti’s devotional literature, which dealt with doubt as well as eternal assurance. The road takes on several meanings, each revealing a facet of Rossetti's contemplation of life and its hardships.