Just from the parking area up the trail till we hit snow.How much off-roading are you planning to do? You made it sound like you were just going to use this to run from the parking area up dirt/logging roads that have some snow and mud on them to a better place to unload the sled (like most people do with sled decks on their truck).
Or are you planning to travel cross country with this?
But from here to there might be a bit on the nasty side with some twisty turnies and ups and downs..