PAIN

As far as I know, this can be done in any mode with snow blowers, and it can be a little tricky. There are 5 Snow Blower Launchers in each environment (they look like large yellow megaphones). If you go through the small end, you will be shot across the environment. You need to get through all of them in a single launch.

The first video shows the order I did them in for Fail Village. The hardest sequence to hit is probably the first two. Each one should shoot you in the general direction of the next, just guide your character into each one. Save your super ooch for the very last one, as you have a ways to travel for it.

Alternatively, you can start with the second launcher in the video, as the last one will shoot you into the general vicinity of the first. Just ooch into it from there. If you're having trouble with the method in the video, try doing it that way... either one works.

This can also be done in the Horse environment (thanks to Dr. Thinker for the confirmation). The blowers are situated slightly different in this mode. There is an in-game trophy called "Horse Coarse" for going through 4 snow blowers in Horse... I've included a video for that below. To use this for Snow Blown, after the last blower in the video, just ooch down to the lake to hit the blower there and get your trophy.