What’s a good goal/habit to cultivate to practice having conversations with strangers?

On my walks, I try to say something like “how’s it going” or an innocuous comment to cashiers and clerks when buying something. And usually in the elevator if it’s just 1 other person but I really want to get to the point that if I see someone i want to talk to, I’ll talk to them. But it feels like I need context to do it otherwise I’m an anxious wreck

Should I try to aim to go to 1 event a week like a wine tasting or boat party or whatever event I want to go to, in the hopes of obviously enjoying myself but the side effect of trying to meet people