Why would it be any more difficult than any other border crossing? There's even a Red Bus tour that takes you to the hotel in Waterton for High Tea. We went; it's very cool.
Sandie & Joel
2000 40' Beaver Patriot Thunder Princeton--425 HP/1550 ft-lbs CAT C-12
2009 Chevy Malibu LTZ with ReadyBrute tow bar/braking system
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Crossing into Canada is no problem, the guards are very professional and you'll be pleased with their welcome! Enjoy your stay at Waterton, it's a neat place and make sure you go in to the big hotel, a classy place!