Riley struggled in his early adulthood, making a living with whatever job came his way (including as a huckster selling bogus medicines). Eventually, he became a bit of a local sensation as a poet and public reader celebrating Indiana culture. After some time, and even a poetic prank equal to his earlier huckstering, Riley became one of the most financially successful poets of the Gilded Age. Even as a nationally recognized figure, however, he was always an Indiana writer first and foremost — earning him the nickname "the Hoosier Poet."
One of his poems celebrating his Indiana boyhood remains among his most famous, "The Ole Swimmin' Hole," which illustrates his light-hearted verse and his Hoosier dialect:
Oh! the old swimmin'-hole! whare the crick so still and deep
Looked like a baby-river that was laying half asleep,
And the gurgle of the worter round the drift jest below
Sounded like the laugh of something we onc't ust to know
Before we could remember anything but the eyes
Of the angels lookin' out as we left Paradise;
But the merry days of youth is beyond our controle,
And it's hard to part ferever with the old swimmin'-hole.
Oh! the old swimmin'-hole! In the happy days of yore,
When I ust to lean above it on the old sickamore,
Oh! it showed me a face in its warm sunny tide
That gazed back at me so gay and glorified,
It made me love myself, as I leaped to caress
My shadder smilin' up at me with sich tenderness.
But them days is past and gone, and old Time's tuck his toll
From the old man come back to the old swimmin'-hole.
Oh! the old swimmin'-hole! In the long, lazy-days
When the humdrum of school made so many run-a-ways,
How plesant was the jurney down the old dusty lane,
Whare the tracks of our bare feet was all printed so plane
You could tell by the dent of the heel and the sole
They was lots o'fun on hands at the old swimmin'-hole.
But the lost joys is past! Let your tears in sorrow roll
Like the rain that ust to dapple up the old swimmin'-hole.
There the bullrushes growed, and the cattails so tall,
And the sunshine and shadder fell over it all;
And it mottled the worter with amber and gold
Tel the glad lilies rocked in the ripples that rolled;
And the snake-feeder's four gauzy wings fluttered by
Like the ghost of a daisy dropped out of the sky,
Or a wounded apple-blossom in the breeze's controle
As it cut acrost some orchurd to'rds the old swimmin'-hole.
Oh! the old swimmin'-hole! When I last saw the place,
The scene was all changed, like the change in my face;
The bridge of the railroad now crosses the spot
Whare the old divin'-log lays sunk and fergot.
And I stray down the banks whare the trees ust to be —
But never again will theyr shade shelter me!
And I wish in my sorrow I could strip to the soul,
And dive off in my grave like the old swimmin'-hole.
Today, the home where Riley was born and grew up in Greenfield, Indiana is open to the public as a museum. The town is also the host of an annual celebration for their native poet's birthday: the Riley Festival.