I've been a passenger in a few scary "pucker factor" towing moments, but that's a longs story.....my own personal incidents where:
1: heavily loaded utility trailer on a light TV (small SUV) in the snow - it nearly slid around and became the trailer dragging the vehicle when I hit a turn too fast...I became more cautious after that near miss.
2: one-ton Dually work truck with about 20K lbs of gooseneck trailer with equipment on it -- came out of a customers yard in and unfamiliar area in Washington DC and ended up in heavy traffic into / through construction zone. Just about the time I realized there where nothing but cars around me, I saw the "no trucks --> " and "<--truck detour" signs go past me as I was, of course, in the wrong lane. I drug that trailer down the wrong lane through the site, zig zagging between a line of curbs, climbing first on one side then the other, while the construction crews gawked at me and I prayed I wouldn't actually damage anything!...It made some awful scraping noises when the dove tail drug concrete...but inspecting it back at the shop it all seemed superficial / cosmetic.
3: Hit a construction zone in the middle of PA somewhere with the travel trailer in tow. I remember it was near Bucknell University. They where working in the middle and had the lane shifted off on to the right shoulder. You entered the zone at speed (50-ish since it was highway) and it narrowed down to just barely wide enough. Traffic was backed up a long way and I didn't want to make it worse. I was trying to stay in the even flow and go. I saw workers ahead move a few cones out more while they moved a machine around. This of course was also right where signs hung over the edge of the shoulder. I gritted my teeth and shot through the "eye of the needle" at speed, aiming for the cones rather than dragging signs along the side of the TT. I at least nicked / shook every cone they'd moved out and ran completely over one and got a shocked look from one worker standing nearby. I thought for sure the wheel well trim of the camper would be damaged when I saw the cone make it flop around, but it turned out to be fine.
