The Kentucky poet had, by then, earned a reputation both locally and nationally as a nature poet. Cawein himself, however, had grander hopes and wrote ambitious works that challenged the evolving world of American poetry after the turn of the century. Many of his works were politically charged, though these were generally ignored in favor of his verses celebrating his rural home state. He died in relative poverty.
Cawein left behind his wife Gertrude McKelvey (it was her birthday on the day of his death) as well as his young son Preston, who later legally changed his name to Madison Cawein II. He was buried in Louisville at Cave Hill Cemetery. Many of the articles reporting his death cited his poem "At the End of the Road" as a fitting final tribute to the poet:
This is the truth as I see it, my dear,
Out in the wind and the rain;
They who have nothing have little to fear—
Nothing to lose or to gain.
Here by the road at the end o' the year,
Let us sit down and drink of our beer,
Happy-Go-Lucky and her Cavalier,
Out in the wind and the rain.
Now we are old, oh, isn't it fine,
Out in the wind and the rain?
Now we have nothing, why snivel and whine?
What would it bring us again?
When I was young I took you like wine,
Held you and kissed you and thought you divine—
Happy-Go-Lucky, the habit's still mine,
Out in the wind and the rain.
Oh, my old Heart, what a life we have led,
Out in the wind and the rain!
How we have drunken and how we have fed!
Nothing to lose or to gain.
Cover the fire now; get we to bed.
Long was the journey and far has it led.
Come, let us sleep, lass, sleep like the dead.
Out in the wind and the rain.
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