A trailer is the last thing I would take up there. But if you are going to take one, make sure you've got extra bearings and spare tires and rims. Because believe me, if it breaks down it will cost you more to get it fixed than to buy a new one. A buddy of mine had a Durango and he took 6 Caribou back on the top. As far as the dates go, the last 3 seasons, Nov. 20 to Dec. 10 have been the best time. Good luck on your hunt.