Welcome fellow prairie dweller.
Best recommendation if at all possible is to get Tobacco while physically visiting the States. If you don’t travel or know anyone who travels that much it’s going to be pricey paying customs fees through the mail, but in my opinion still worth it as long as you’re just exploring pipes as a hobby.
I know lots of people hate the idea of being forced to smoke outside but I LOVE spending time outside, spending a few hours puffing smoke in the old barn or under a tree watching the sun set is just a dream come true.
For pipe smoking in -20 get one of these https://eglifarm.com/collections/hats/products/head-honcho-hard-hat-liner and put some of these https://eglifarm.com/collections/boots-and-liners/products/sheepskin-bootliners-adult-1 inside some jumbo snow boots. Make sure to get some practice lighting with matches since liquid fuel doesn’t work in the cold (unless you keep the lighter in your armpit).
And if you ever do visit the states, make sure to get your fill of Cigars. I know this is a pipe forum but with the way regulations are set up you can get about twice as much Cigar Tobacco across the border as you’ll get in Pipe Tobacco tins (make sure to get both though, so one trip should bring in about 600 grams of tax free Tobacco).