Not a road but just as funny.
Back in the early 80's I worked at the Airfield in England that hosts the big airshow every other year. I also flew gliders there most weekends.
Well we had not been able to use one of the runways for about 8 months becuase it was getting resurfaced, unlike the main runway this smaller one did not have a concrete surface but an asphalt one.
They finished the surface about a month before the airshow, due to wind directions we only got to use it once when aircraft started arriving for the show. Well the biggest transport in the world at that time was russian and when it landed they hooked up the tug and proceeded to tow it down the new runway, they got about 50' before they stopped, they aircraft had sunk into the asphalt and it looked just like a tractor going through a muddy field. The powers that be decided that it wold be easier to go forward than to try to go back. To this day I wish I had a photo of that one.
Initial cost of the resurface was 1 million pounds.