The step on the near corner of the lower roof (above the Public Telephone sign) makes me think that this is a former electric streetcar with the front platform chopped off.

"D" series International (Harvester) circa 1938-1939

I would imagine the "ladies" depend on the truckers, too.

I'm pretty sure this diner was on U.S. Route 11, just north of Cortland and just south of Homer. The coal truck is pointed north, toward Tully, Lafayette, and Syracuse, about 35 miles away. The valley bottom is so flat that the river used to flood a lot in this area. I suspect those are riverbank willow trees behind the diner. The Tioughnioga flows south and joins the Chenango River, which flows into the Susquehanna near Binghamton; so this diner is in the northernmost headwaters of Chesapeake Bay.

Cortland was the home of Brockway Trucks, and was called "The Crown City" because its elevation is the highest of New York State's 62 cities.

Homer, Cortland County's prettiest village, billed itself as "The Homeville of David Harum," the fictional horse trader.

There used to be a place in Clarence (a small village some twenty or thirty miles east of Buffalo) that converted old passenger train cars into these diners and supplied a number of towns in New York State and northern Pennsylvania. They had a siding that ran up to the building to load them onto flatcars for delivery to other towns along the line. After the company folded, they sold the structures to Erie County, which relocated one of its Highway Division maintenance barns there. As a surveyor for the County, I worked out of there for a number of years.

While stationed with the Air Force in Niagara Falls, NY in the 60s, I drove a coal truck part time much like this one (we didn’t have much to do on AF duty). Like this one: beat-up, under-powered and once you got it rolling, a real bear to stop, my old Ford truck got the job done, and helped keep part of “The Falls” warm through those cold Upstate NY winters!

Booths for ladies.
Tables for ladies.
If she sits at the counter with the truck drivers, she's no lady.

They had me at The Home Of Perfect Food.

and maybe too cynical. This is a diner, not a truck stop. Why is a diner recruiting ladies to come inside also offering free bunks to truck drivers?

bobzyerunkl, point taken. But if she climbs into a free bunk with a truck driver, she's no lady either.

My late mother-in-law, who hailed from anthracite country, used to regale us with the story that she and her siblings had to walk two miles to and from school (both ways uphill, of course) in all weathers, unless they "could get a ride on a coal truck." I wonder if this was one of them.