By far for me it has to be Sand hill in Wheeling, WV. I read a glowing article about it in the newspaper about how wonderful it was that this guy built a new executive course even when people told him he couldn't. So I decided to try and play it. It turns out those people that said he couldn't build a golf course was right.
It wasn't a golf course. It was a death trap. Pretty much the whole thing was on a very steep hillside. So steep that rolling a golf cart was very likely, Despite the fact that the guy said they won't roll and to drive them at an angle down the hills ( Apparent this guy never heard about center of gravity.), Ended up returning the cart after 2 holes because I Actually had to lean off the side of the cart just to keep it from flipping.
I had to make a 10 footer for 9 on #3 partly because I was still shook up from nearly rolling down the hill with the cart.
The greens couldn't have been more than 30'x30'. One of the worst holes was a 240 yard Par 3 (Witch is of course on said steep hillside) that had OB on the left so anything short was gone. But as long as you could hit it 240 yards dead straight and land on a green the size of the hood of a car you were fine. When I asked why it was 240 Yards (Since it was supposed to be an executive course) He said it was a mistake. Witch means he actually printed the cards with the wrong par. Despite how tempting it might have been, I did not tell him that building the course in the first place was a mistake. Even though I think it's true.
I almost quit after I think the first 6 holes, But since I like to torture myself I continued anyway.
Another lowlight was the 180 "Par 4" hole with a blind tee shot. I made a "Par" on that one.
The 9th (And thankfully last) hole of this abomination was a short one. Straight up yet another cliff. I ended up snap hooking the ball into the trees, lost it, and made a triple bogey, A fitting end to a horrible day.
In the end it was obvious that this gut knew NOTHING about golf, But decided to build a golf course anyway despite people warning him it was a bad idea. The sad thing about it is the owner is actually a pretty nice guy. He just had no idea how to build a decent golf course nor does he know that running golf carts on hills that steep is a lawsuit just waiting to happen. The scary thing is, I think that course is still in business, Although I haven't (And never want to) been back.