Here's famous Civil War cigar token. The hotel had a gentlemen's lounge here men could smoke cigars, play billiards and catch up on the news of the day with the latest newspapers. This is a scarce token, but most of the examples I have seen were Mint State.
510 Edmond St, St Joseph MO is probably where you want to go to cash it in, although it's a coffee shop now. https://buchananmo.devnetwedge.com/parcel/view/063008003002042000/2025 looks like a great place for a cigar store. I can't find building info there but the subdivision is "original town" so it's likely quite old. I have more important things to do today but I don't want to.
I saw that one first and figured Pittsburgh would be a likely place, but then noticed that it's a house. St Joseph MO seems like a good bet, given the history as a last place to get supplies before heading into the Wild West. Can't start a new life as a sodbuster without some cigars! https://en.wikipedia.org/wiki/St._Joseph,_Missouri#History Edit - I don't know how that image got attached here. Can't delete it in edit mode? Totally unrelated!