Winter 2011-2012 in Michigan’s Upper Peninsula (Escanaba area if that narrows it down for anyone). Me and two buddies get the bright idea to go take a 2WD 1998 Dodge Ram down some snowmobile trails because it had been a “mild winter” and because we’re dumb. Actually making good progress until we come to a fork in the road. We take the right fork, make it about 20 feet and we stop dead. Zero forward traction zero backwards.

So we get out of the truck and start trying to dig it out when we realize it wasn’t a fork in the road, we had driven straight over a snow filled ditch into a farmers field. If there wasn’t any snow the truck would have been levitating over 2 feet above the ground. No cell service because it’s Michigan so we walk a mile or so back to the last farm we had passed on the trail to see if the farmer could pull us out. He says sure, but we have to help with chores which long story short ended with me helping this ~80 year old man birth a calf in the freezing ****ing cold.

So finally he comes to try and pull us back on the road with a K5 Blazer, which proceeds to also get stuck. It’s pushing 9pm in a Michigan winter at this point. The old man makes Gator walk back the mile AGAIN to go get his wife to come pull us out. Almost an hour later here comes this old woman on a big yellow Oliver dozer to pull both trucks out. They wouldn’t take a dime for all the trouble. It’s probably not the most stuck anyone has ever been, but it’s by far my favorite experience when this question comes up.

TLDR: Got a Dodge stuck on a snowmobile trail, got a Chevrolet stuck pulling it out, a woman who might have been born during the Great Depression pulled both trucks out with a bulldozer