I drive for Roehl. I've hauled loads through Canada a few times from Maine through Canada into Michigan. On two other occasions I was sent into Canada empty to haul loads back into the USA. We get $25 crossing the border, so $50 for in/out of Canada. Driving through (in transit) isn't much paperwork. Picking up in Canada and delivering in the USA is significantly more paperwork and involves phone calls and emails or faxes. I actually just ordered a printer/scanner for my truck to streamline that process. That's my experience with Canada thus far.
Dustin, I don't know of any companies that actively go into Mexico. The risks are just too great down there of having your truck stolen or secretly loaded with contraband or who knows what. I have carried freight that goes to Mexico, and also picked up freight that originated in Mexico, but practically every trucking company that does any business in Mexico has drop yards at the border and you simply either drop your trailer at one of those yards or pick up a trailer at one of those yards, I have even had to meet a Mexican truck at a yard and then have a fork lift operator transfer the load to my truck or vice versa.
I can't answer your question about Alaska. I have been told that we have a load that goes to Alaska on occasion, but I have yet to hear of it again and that has been three years now since I heard this rumor. I was promised to get the first shot at it when it came up again, but all has bee quiet. So, I'm still holding out for that one, but I quit holding my breath over it a long time ago! It is going to be very rare that you would go to Alaska. Canada is your best bet if you want to cross the border in an eighteen wheeler.
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As a company driver, how often do you get to go to Mexico, Alaska, or Canada? Just currious