I had won all kinds of crazy awards, most of them due to my location - in small EU country. For our people, it is too impersonal to just give the envelope with cash, so the race organizers always give trophies (which is OK, most of them are nice, even precious - made of crystal) and most often then not add a personal gift, usually conected with the locality.
Thus I had won live pig, 2 ducks (fed and ready to be slaughtered), 8 chickens, burlap sack with 30kgs of lentils, which I ate for 2 years and had to throw away the remainder because it became moldy, one rabbit, airplane tickets worth 25.000miles, spa vouchers for 2 persons for week stay (I have won it 3 times), and all kinds of vouchers to hotels. Mind you, some of those gifts were pretty valuable, worth many times more than the cash prize (usually between 200 and 1000 dollars at medium races, more at big races). Some of them were plain crazy - like the live pig, which I had immediately sold to the local farmer, and the RD got angry at me for that.
But the best story happened to me in the late nineties in the US: I placed second at a large race, won over 10.000 bucks, but the RD appologized in advance for the delay in payment, because of last moment financial problems caused by the main sponsor. Half a year later I still didn't see a dime, so I just gave up and wrote it off. The RD sent me a personal letter in which he had appologized and invited me for the next year's race. I wasn't sure about coming, despite new sponsor and lots of promises, but 2 months before the race, I had received full amount plus the comped entry and show up incentive. I had written a personal thank you letter to the RD and sponsor as well. The bad thing was that I had to drop out of that race 8 miles in because of injury. I felt so bad, but the RD told me to keep money and return next year. I had been racing there 11 times since then and won on several occassions. Good times, and am good friend with the RD ever since he acted like a classy gentleman.