Easy enough to do. Did it twice, both times with my wife on the back (the ole' center of gravity thing).
Once while cruising through some back roads of eastern PA we came to the end of a paved road. Been on gravel - dirt before (and with my wife as a passenger) so we kept going - downhill.
It got to a point we all decide (4 of us in the group) that at the next level spot were letting the girls off and continue without them (only an 1/8 mile or so)
Soon as I slowed to stop I hit the soft stuff. So slow you just step off the bike. Had 3 helpers to pick it up that day. Hard enough on pavement let alone gravel.
2nd time I was in Gatlinburg, at the hotel at the top of the hill in town. The road has a screwy hairpin turn, worse then anything on the dragon.
Anyway, we leave the hotel, the bike is really loaded up, as my wife flew down and I picked her up at Nashville airport.
All my junk, her travel bag (I'm sure it was well over the luggage rack recommendation), a new heavy Foxcreek leather jacket I bought for on the way down (sitting under her gearbag) and I was sitting on an air hawk cushion (another inch or so in height.
SO we go down the hill with no problem as we had been doing for 3 days.
Once at the bottom my wife says "do you have my cushion" (for her lower back).
Nope - so we turn around and head back up the hill still no problem.
Half way - on the turn - I see pickup coming with the guy holing the cushion out the window - cool - so instead of just continuing and grabbing the brass ring I decide to stop, up hill, on a turn, with a camber - duh there was no way to stop - another slow motion "there she goes.
We step off - I bitch and moan - the guy in the truck stops to apologize

and he helps me pick it back up. Stupid move on my part. The rest of the trip was uneventful - until I hit that thunderstorm on Grandfather mountain - but that is another story.