There was a TV episode of a man that cannot find his way into or as I remember out of a town. On returning to the town he stops at the same isolated diner over and over again. The diner is inside or outside the town limits. He is traveling alone in a car. And the road signs, probably at forks in the road, steer him in circles. I can’t locate the series or episode.
I recall seeing it between 1996 and 1999. I thought it was Outer Limits but as I said I can’t find it.
Could this be Southbound, an anthology of indie horror short films?
The first story seems to match elements of your description;
The anthology begins with "The Way Out and The Way In." Three more are quickly on there way. In this short two friends are chased by grim reaper like ghasts. Jack (Matt Bettinelli-Olpin) and Mitch (Chad Villella) cannot escape as all roads lead back to an isolated diner.
I figured it out, it was a TV anthology movie called ESCAPES 1986
An anthology of five tales of terror, each originally produced for video. The titles are "Something's Fishy," "Coffee Break," "Who's There," "Jonah's Dream," and "Think Twice."
Coffee Break Young trucker is rocking out to hard rock/metal music and asks an old man for directions as he keeps looping through the town. He tells him if you slow down, enjoy the scenery and stop (at a Diner in the town) for a nice cup of coffee, he'll get out and find the highway. In the end, he goes into the diner where he's confronted by everyone and the old man forcing the pot of coffee towards him and he asks, "what do you people want from me?" After drinking the coffee, he becomes the town's newest resident and the sign changes the population count.
