the craziest thing i've done on sled would be trying a backfilp off the back of a sled off a jump or doing no footed can cans off my friends dirt bike jump or jumping a 50 foot gap on sled (yes i said gap not the full jump just the gap)
I was coming around a corner once and met a guy on the wrong side of the trail. I went on his side and he went on mine. We played chicken and almost tapped skies. Scared the living shit out of me though.
mine would be last year, i was climbing up into a rock shoot, got about 50' from the top, turned to come back down and slammed into one of the rocks, wrecked a trailing arm and a front bracket. Then it rolled about thrity times and wrecked the hood hinges and tore the hood a couple inches. It hit the rock 900 vertical meters from the bottom of the hill according to the GPS. that was kinda scary.
I think the craziest thing I ever did was rode the edge of I 94 in central MN. for about 40 miles doing 90 to 100 mph the whole way on my 89 650 Polaris ported and piped We had a ton of snow and the edge of the road was like a groomed trail. It sure was fun seeing the look on peoples faces when you passed them in their car. Fastest 40 miles I have ever made. Riley
december 25th 2002, best christmas present ever, 3feet of snow in less then 12 hours, at a rate of 3to4 inches an hour at times, opened gifts and was like PEACE, heard scanner say police cruisers were stuck in the parkin lots, couldnt get out,,,,
we rode the highways, streets, side walks all day, 6 of us drag racing down main streets from street light to street light, passin the cars that were out and not stuck like they were parked, cops couldnt do nothing it was great, too bad everything was closed cause of the storm and it being christmas day, would have been cool to goto mcdonalds on sleds in the city...
we still have almost a 2 foot base on the trails and snowing like crazy now
i would be with riley, i have done alot of crazy things for my age but the craziest thing would be this winter when i was messin around with my friend i would go down in the ditches and dissapear then when i hit the approaches i would fly with him...lol it was fun till he we got to the city limits... and he drives a mustang hehehe,or the time i climbed a killer hill....well to make a long storie short i wasnt used to studs there wasnt alot of snow and i fliped it it was a pretty steep hill
I havent really done anything crazy, but i know a movie that is AWESOME!!! i cant believe some of the stuff they do on it. Its called Redneck Fury if you wanted to know. There is a 100 foot gap on it that one guy clears and then biffs pretty bad on the landing. I think the movie is awesome! [8D] I'd say the craziest i have done would be...taking my 1971 Ski-Doo Olympique 399 off-road into the woods. It was pretty cool, tipped it twice got buried a bunch of times. Thats all i can think of that was "crazy" for me.
I haven't done too much crazy stuff on my sled, there hasn't been any good storms to close everything down since I've been riding but if there was I'd take a road trip with me sled! The craziest was with my old polaris we got a storm and everything froze into ice. I flattracked around the yard with the sled kicked 90 degrees out from the forward movement most of the time. That was fun! I've done a lot of jumping snow banks, piles and drifts but nothing real extreme. Now my motox bike...thats a bit different of a story 
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