Canada went straight to Chip & Pin, skipping over Chip & Sign. Since credit cards generally didn't have PINs at the time, there was a little work on the part of the issuing banks to assign PINs. One of my cards came with a letter that said "Use the same PIN as you use with your regular bank card", another came with one that said "Here's your new PIN, you can change it at any of our ATMs" (I only have a credit card with this bank). This all happened over 10 years ago.
When I visited the US recently, I used one of my cards and the cashier said "Oh, you're from Canada, you have to enter a PIN" after inserting it into the payment terminal. A payment at Walmart was even easier as the terminal was customer-facing, it worked just like it does in Canada - insert card, verify amount, enter PIN, done.
Clearly the infrastructure is in place, since the transactions all worked, but there seems to be some strange reluctance for the card issuers to actually use it.