There are many roads in New York State called “Stony Lonesome Road” (including one in the town where I grew up, and one in West Point). Now I learn there’s a stream in Alabama, a town in Indiana, a bluegrass band from Minnesota, and a poem by Langston Hughes of the same name. There’s also a novel called The State of Stony Lonesome.
For years I assumed it referred to a sparsely populated place with rocky soil (which describes the area along the Stony Lonesome Road of my hometown). When I searched Google for the phrase, I couldn’t find a definition. I did come up with some sites that seem to imply that it refers to a cemetery (a lonesome place with headstones?), but more that seem to imply that it’s a jail (a lonesome place with stone walls?).
What exactly does it mean, where did it come from, and when was it first used?
Ah, good ol’ Stony.
The lanky son of Gabe and Myrna Lonesome.
Stood exactly five feet tall and weighed in at an impressive 87 pounds.
I went to college with him. A boxer he was. Could barely lift twelve-ounce gloves to protect himself in the ring. Had a cauliflower ear and a nose that pointed that-a-way. Fifteen amateur and thirty seven professional fight, and he never won any of 'em. Could be counted on to drop before the end of the first round. I once actually saw him soil himself when he found out that he had to BACK in the ring for “round two”.
I’ll miss Stony.
Was sucked into a stormdrain one rainy evening and never seen again.
<removes hat and dabs away a tear>
As far as the OP goes, I’ve heard stony lonesome used as a euphemism for prison. Only a few times though; it doesn’t seem to be very common.
Not that The Simpsons is any kind of reputable reference to cite, but I recall one episode where Bart and his friends are playing near the abandoned prison. “Ah, Old Springfield Prison,” Bart says (and I’m paraphrasing; I cannot recall the lines word-for-word), “the Big House, Up the River, the old Stony Lonesome…” He goes on stating all kind of euphemisms for prison for a while.
Doesn’t help explain the roads, streams, and towns using the name though. Maybe there was once a prison or a jail on or near them…?
I’ve also heard stony lonesome used as a euphemism for prison, in sort of an old-fashioned way. Or at least the term seems old-fashioned to me, like maybe turn of the century. I’m guessing places with this name were once associated with prisons some time in the past.
BTW, I think “Stony Lonesome” would make a good name for a thoroughbred race horse.
It’s a good term for getting high alone, too 
— G. Raven