"Roads Go Ever On" is a walking song that Bilbo Baggins sings for the first time in chapter 19 of The Hobbit. Bilbo's first rendition of the poem conveys a feeling of weary relief as he gazes across the Shire after his long and dangerous journey. Bilbo's song seems to be a reflection on his journey, almost a self-congratulatory "job well done, Bilbo."
Bilbo sings other versions of "Roads Go Ever On" throughout Tolkien's Lord of the Rings trilogy. The songs generally mark a major transition period in Bilbo's life. For example, he hums the song after he gifts the One Ring to Frodo and leaves the Shire in Fellowship of the Ring. Bilbo's new journey is filled with "eager" hope to start his book and a new life free of the Ring.
Bilbo is old and weary the final time he sings "Roads Go Ever On" in The Return of the King:
The Road goes ever on and on
Out from the door where it began.
Now far ahead the Road has gone,
Let others follow it who can!
Let them a journey new begin,
But I at last with weary feet
Will turn towards the lighted inn,
My evening-rest and sleep to meet.
Bilbo gracefully acknowledges that his journey is complete and gives "others" a blessing for "a journey new."