As a Canadian living near the border (as many Canadians are!), I would often drive into the US for shopping. There are a number of towns that seem dedicated to serving Canadians, like Watertown, NY. I've found that often the US border guards would be much nicer than the Canadian border guards, probably because the Canadians are the ones that need to deal with the customs rules (Canadians aren't trying to smuggle their new purchases back to the US without paying tax!).

I haven't been on a shopping trip like that in a while though, and I find it hard to believe I'll ever do it again now. I feel bad for Watertown, but with the tariffs and the risk of detention, its not worth it.