I've always said "HELL-uh-nuh" without a second thought, but suddenly wondered if I have been wrong all these years. A quick Google check yielded The Montana Pronunciation Guide. I determined that I'm OK on Helena, but woefully ignorant when it comes to many other Montana locations.
From here, I continued down the Google rabbit hole and came across Reader's Digest's list of the most difficult-to-pronounce town in each state. I knew around ten of them for sure (my parents grew up near Puyallup, Washington) and made some educated guesses (California has Butte County, so I was confident that Crested Butte, Colorado would be pronounced the same way), but I definitely botched most of them.
Then I came to this list by USA Today. Again, a few were really easy for me but most were not. I have some connection or familiarity with the ones I got right, aced the ones with Spanish pronunciations, and lucky-guessed a few others. The rest, nope!
Anyone have any interesting city names near you? Let me know how to pronounce them correctly so that I don't sound like a clueless tourist when I eventually visit!