The Long Dark (UP)

This is the second story related mission. Once you leave the Community Center, you should see the burning plane in the mountains. (If not, you will soon.) The best way to get there is to leave the center and turn left. (Make sure to loot the store across the road.) Cross the bridge and keep following the road. Keep following it all the way around until you finally get there.

The achievement won't pop until you pass through the first part of the plane and jump down.