Down from the door where it began.
Now far ahead the Road has gone,
And I must follow, if I can,
Pursuing it with eager feet,
Until it joins some larger way
Where many paths and errands meet.
And whither then? I cannot say.
As a kid one of the many things I loved about The Hobbit was its maps. The map of the Wilderland just inside the front cover of the book (see picture above) had a dotted line that crossed the Misty Mountains, followed the Old Forest Road, and, if you turned North when you reached the River Running, took you past the Long Lake and to the foot of the Lonely Mountain. I recall tracing the journey with my finger and at times letting it wander (not too far) into Mirkwood on either side.
The Road as life
Tolkien says that the Road can sweep you off your feet, implying that it has an element of wildness and chance about it. It can take you to places you never expected. You may face hardships and perils or death in a foreign land. You may find great wealth, or the last refuges of magic, in realms where time seems to stand still.
But the Road always starts with a simple choice, and that is the decision to set your foot upon it. It starts with humble beginnings, from a single door in Bilbo's case, but if you follow it long enough it will take you to an intersection of many paths and errands. This very much parallels the course of a life, in which a child has but a few options but eventually encounters the many freedoms (and perils) that come with adulthood.
In his walking song Bilbo cannot say where the Road eventually leads, because eventually choice intersects with chance. We can choose our own direction on the Road, for good or ill.
In my "normal" suburban life even I feel a tinge of fear and thrill of the unknown when I step onto the Road and leave my driveway on some long business trip, of which I typically take at least two a year. And I'm always amazed and relieved to find when, after boarding a jet plane and traveling 3,000 miles across the entire country and back again, I find myself once again at home with my family.
It may not be the Misty Mountains or Mordor but it's about all the excitement I can handle.
The Road as death
Of course, eventually we all must reach the end of the Road. Tolkien offers four versions of Bilbo's walking song in The Lord of the Rings; each time the teller (alternating between Bilbo and Frodo) is further along in the Road of his life.
The first time we hear Bilbo's song it's the quote I started with above, and it's full of energy and anticipation of the journey. The second time, Frodo sings the song and he has begun the long trek to Mordor. In place of "eager feet" we get "weary feet." He is feeling the weight of his great task, just as we feel the adult weight of jobs, responsibilities, and age.
In "Many Partings," we hear the song for a third time. Bilbo knows his traveling days are winding down when he sings:
The Road goes ever on and on
In The Road to Middle Earth, author Tom Shippey states that Bilbo here is equating the lighted inn with Rivendell, which is his literal next stop, but that he is also referring to his own death.
In "The Grey Havens," the final chapter of The Lord of the Rings, Frodo sings Bilbo's old walking-song one last time, though the words have changed much:
In other words, there is a new Road to take at the end of our lives. It is a road hidden to mortal men, perhaps always under our noses ("oft have passed them by") but invisible to our senses. No living man (nor hobbit) has ever started down this road.
According to Tolkien's cosmology, Middle-Earth was once flat, and you could reach the Undying Lands if you sailed far enough out to sea. But the Numenoreans abused this opportunity, and as punishment the Creator gave Middle Earth its present round shape. The straight Road was lost, and now only the elves can find the Grey Havens.
Man has a different final Road to take than that of the elves, one that Tolkien hints in his cosmology may lead his soul, freed from his body, back to the Creator.
My own Road
I'm glad to say that, right now, my Road runs straight through Middle Earth (right now I'm listening to The Lord of the Rings as I drive Route 95/114 to work; hardly Bilbo's garden path or the East-West road running out of the Shire, but it will have to do). Middle-Earth is becoming a well-trodden and familar path but I never tire of taking the trip.
If there is an afterlife, I hope with all that's in me that I will awake at the end of my Road to find myself in Meduseld, the golden hall of Theoden, my current stop in my latest re-read of The Lord of the Rings. Even better, perhaps I may one day find myself enjoying a fine beer at The Prancing Pony, listening to the locals tell a queer tale about a hobbit from the Shire and his companions who fell in with a mysterious ranger from the North. Time will tell.