For a winter alcan trip with a trailer here is my list (what I’ve actually used and/or needed on the trip)
A cell phone plan that allows unlimited talk and text in Canada (rogers wireless)
Spare tires: one for the truck and one for the trailer. If you are on a budget and don’t own a spare trailer tire, buy one at Walmart that is mounted and ready to go. If you don’t need it on your trip, return it at the Walmart nearest your destination. (Kenai)
Spare serpentine belt for your vehicle (and know how to change it w/o a YouTube video bc Murphy says you probably won’t have cell service when you need to change it)
Shovel: a collapsible snow shovel or two for if you go decide to go ditch diving…
Basic truck repair tools: fuses (large and small for both fuse panels) sockets, wrenches, pliers, tire jack, sockets that fit your trailer lug nuts, basic electrical connections (for trailer lights), rtf silicone, electrical tape, Allen keys, etc.
Tow strap: if you are on a budget, buy 35’ of Amsteel blue stiff lay line and splice an eye in each end = ($10 tow strap that is rated at 15k instead of the standard 10k)
Tire chains: v bar, standard or my personal favorite for Hwy use - cable chains!
Pet health certificates for the boarder crossing if you are bringing pets
Do Not Bring: guns, ammo, reloading components, etc. ship these to AK using Carlisle Connect (google it) and pick it up at the depot on bridge access rd. In Kenai.
No beer or booze: it’ll be a headache at the boarder
Buy in Canada: gas cans! (at Canadian tire, if you know, you know, if you don’t, you will!) Canadian gas cans don’t have the ******* nozzles mandated by CA… **fill the gas cans so you have a bit of extra fuel, the shot between ft Nelson and Watson lake is long if toad river gas station is closed or out of fuel**
Road-trip stops: Tim Horton’s for breakfast and laird hot springs.
If you make it to Alaska with a wife and a pickup truck that both work… then you are living the Alaskan man’s dream!