Oregon Trail
copyright 2011 by Tim Griffin

Mister Smith was born in Boston, no particular family
No education, no connections, and no opportunity
But he heard about a land where no one cares where you’re from
And he wants to be where land is free to anyone who’ll come

(chorus) Fare thee well to old Saint Louis, now we’re up and bound away
We’re headed through Missouri out to Californi-ay
Wagons ho, there’ll be no one to tell the story if we fail
But we’re all bound for glory on the Oregon Trail

Mr. Paddy hails from Dublin, he’s as good as apple pie
But in New York he saw the signs that read, “No Irish Need Apply”
Still he swore to find success, ‘twas his father’s last request
So he left New England in his dust and now he’s heading West

(repeat chorus)

Mister Jackson was a model slave, he needed no chain
And his master’d be amazed to find him on our wagon train
Master sold him down the river, he took a detour on the way
And it fills our hearts with courage every time we hear him say

(repeat chorus)

Mister Parson is a preacher, reads his Bible all the time
And he reads outrageous revelations in between the lines
Now his soul’s in mortal danger and his life’s in danger too
Joined our caravan of strangers ‘fore his parish could pursue

(repeat chorus)

Now you’ll seldom see the best and brightest leave their lives behind
It’s the outcast and the misfit need a better life to find
Let the gentry keep their East Coast, it’s the easy road they choose
But the West is won by lesser sons with nothing else to lose

(repeat chorus)


For years I fiddled with some lyrics about American expansion into the West, cataloguing the dangers and the places, but I never did get a satisfactory song out of it. I finally discussed it with a professional storyteller who explained I was telling the wrong story: instead of writing about events and places, I should focus on the people who would undertake such a journey and why. After that, the song took less than a day to write. It’s amazing how a fresh perspective can untangle a problem.

By the way, I should acknowledge right now that although this song addresses prejudice and racism among the settlers, it does nothing to address the fact that the land they settled already had a resident population who drew the very short end of that stick. I have a few unfinished songs about the expansion of the United States from the natives’ point of view, and I’ll post them when they’re done. My goal is to tell our stories from many perspectives, but I don’t know how to make one song tell everyone’s story.

Here are some content standards for the state of California addressed by this song:


  • CA.HSS.K.1.2. Learn examples of honesty, courage, determination, individual responsibility, and patriotism in American and world history from stories and folklore.

Fourth Grade:

  • CA.HSS.4.3.2. Compare how and why people traveled to California and the routes they traveled (e.g., James Beckwourth, John Bidwell, John C. Fremont, Pio Pico).
  • CA.HSS.4.3.3. Discuss immigration and migration to California between 1850 and 1900, including the diverse composition of those who came; the countries of origin and their relative locations; and conflicts and accords among the diverse groups.

Fifth Grade:

  • CA.HSS.5.5.8. Discuss the experiences of settlers on the overland trails to the West (e.g., location of the routes; purpose of the journeys; the influence of the terrain, rivers, vegetation, and climate; life in the territories at the end of these trails).

Eighth Grade:

  • CA.HSS.8.4.1. Describe the country’s physical landscapes, political divisions, and territorial expansion during the terms of the first four presidents.

...and of course, we do map skills in every grade so you can always use this as a chance to study geography.

Guitar Chords:
C, G, C7, F, Am, Am7

"Oregon Trail" tied for a Pegasus Award in 2018 as the Best Road Trip Song; the other winner was Heather Dale for her extraordinary song, "Road To Santiago."