Does this ring a bell? I have been meaning to systematically collect songs about whippoorwills. Maybe this thread will attract some more.

THE FIRST WHIPPOORWILL
As recorded by Bill Monroe on "The Music of Bill Monroe" (1982)

1. Springtime is near, my darlin'.
You say that you are goin' away.
My heart will be with you, my darlin',
And I'm countin' now the days

CHORUS: I know that soon I'll have to travel.
I know I'm over the hill.
I feel so all alone; my darlin' said she'd be gone
When I heard the first whippoorwill.

2. The flow'rs are bloomin', little darlin',
With the buddin' of the trees.
I hear them night birds a-cryin'.
I know that they are warnin' me. CHORUS

3. Our love was planted, little darlin',
Just like the farmer plants his grain,
But there will never be a harvest.
On the hill, the whippoorwills now sing. CHORUS