The old Ralston (Nebraska) High School course located at Ralston Park was brutal. It was 2.6 miles, and had a hill you nearly had to crawl up 80 yards from the start, then two laps of a course that was probably 40 percent uncomfortably off-camber. Two 200-300 meter hills were included on each lap, with one another off-camber crazy thing that then passed where the starting hill dumped off.
A rock parking lot made up about 200 meters of each lap, leading to a dozen or so twisted ankles each race.
The school relocated the course to a soccer complex area after 20 years or so, making it 5K now, but also making it a flat course like everything else.