If your truck is equipped with Tow/Haul mode then it is recommended you use it whenever towing or hauling.
But as mentioned before you need to learn what your T/H does. Some of the older rigs only disabled the overdrive. My '11 Ford does not disable the overdrive. Still goes into OD whenever the computer deems it safe. But the T/H does change the shift points to keep the RPM's from going too low.
I've never been back East so I can't comment on the grades. But here is some interesting reading.
Top Ten Toughest Pulls