I am unable to answer your query, but there was a thread on the song in which Abby Sale posted the lyrics:

Click Here

Unfortunately, it does not answer your query either. I have seen it written as 'Helarie', but that seems to make less sense than 'hilary'. I think that perhaps Rogers was suggesting 'from hell to hilarity' but wanted a rhyme for 'prairie' and so put 'hilary'. Just a thought.

--Stewie.

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Thread #17944   Message #175089
Posted By: Abby Sale
08-Feb-00 - 01:33 PM
Thread Name: Lyr Req: Santa Fe Trail
Subject: Lyr Add: SANTA FE TRAIL (James Grafton Rogers)^^

Loverly song. Slim Critchlow.

THE SANTA FE TRAIL
by James Grafton Rogers, 1911

Say, pard have ye sighted a schooner
A-hittin' the Santa Fe Trail?
They made it here Monday or sooner
With a water keg roped on the rail,
With Daddy and Ma on the mule-seat
And somewhere around on the way
A tow-headed gal on a pony
A-janglin' for old Santa Fe
Oh -- Ah – Oh --
A-janglin' for old Santa Fe.

I seen her ride down the arroyos
Way back in the Arkansas sand,
With a smile like an acre of sunflowers,
An' her little brown quirt in her hand
She straddled the pinto so airy
And rode like she carried the mail,
And her eyes near set fire to the prairie
'Long side of the Santa Fe Trail
Oh -- Ah – Oh --
Alongside of the Santa Fe Trail.

Oh, I know a gal down on the border
That I'd ride to El Paso to sight;
I'm acquaint with the high-steppin' order,
And I've sometimes kissed some gals goodnight;
But Lord, they're all ruffles and beadin'
Or afternoon tea by the pail,
Compared to the kind of stampedin'
That I get on the Santa Fe Trail
Oh -- Ah -- Oh --
That I get on the Santa Fe Trail.

I don't know her narne, and the prairie
When it comes to a gal's pretty wide,
Or shorter from hell to hilary
Than it is on this Santa Fe ride,
But I guess I'll make Cedars by sundown
And campin' may be in a swale,
I'll come on a gall and a pinto
Alongside of the Santa Fe Trail
Oh -- Ah -- Oh --
Alongside of the Santa Fe Trail.

11/16/1821: William Becknell party reaches Santa Fe, N.M. - 1st use of Santa Fe Trail
^^^

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added to DT October 2000

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(tune from Katie Lee's Ten Thousand Goddam Cattle -Joe Offer-)