I tried to get my '85 Westy through that tree 2 summers ago. Even heavily loaded from a camping trip (to Prairie Creek Redwood State Park - a great campground btw) it would not fit (at the very best it was going to be less than half an inch clearance, which was enough for me to chicken out, even with encouragement from the back seat).
Most disappointed, especially since I had to pay ($4?) to drive down the private road to the tree....
I haven't had a chance to try my '87 Westy yet - perhaps that will ride a little lower (the '85's are supposed to be the highest riding Westys from what I have read on the list?)
Mike
'87 Westy