Strangest ride would probably be the day the neighbor's dog decided it wanted pig for dinner.
I was riding my then 4yr old in my trainer's arena, I was alone as she was ill and was just going to have a quiet walk only ride as my horse needed a break in his training. All of a sudden the neighbor's dog decided their piglets, who are penned right on the other side of the arena looked yummy and went after them. Holy cow, who knew a pigs could scream like that!
I am trying to keep my terrified gelding from falling apart, pigs are screaming, the dog has one pinned and their other dog is barking it's fool head off. Their sheep and chickens are going bonkers, their ancient bomb-proof horses are viewing the chaos as free entertainment.
I'm stuck, if I yell at the dog, my horse will lose it completely and dump me. I can't get off and go get the neighbors because I'd have to go past their dogs and the pig-killing dog is not friendly, had a run-in with him previously when he went after my horse and there is absolutely nobody around. I can't get off and hope someone comes because my horse who is remarkably un-spooky under saddle, is beyond spooky on the ground and he's so worked up that if I get off, he's going to lose it completely and there's a good chance of him running me over.
Finally, the neighbor's hear their pigs (they must be hard of hearing.... half the state heard the screaming I'm sure!) so the Mom and kids come out. The Mom stands on the back porch screaming at the top of her lungs at the kids. Brilliant, just brilliant, that was about all my horse needed to finally lose it, so I'm off on a wild ride, stupid pigs are still screaming as although the dog got dragged off, the kids are now chasing them in circles.
Kids finally stop chasing the pigs and I got him under control. So much for my nice, quiet ride!
Thankfully said dog attacked their sheep a few nights later and they got rid of it after that.