In my city, an older guy organized an “urban hiking group” where he would plan walking routes through the city, usually stopping at a restaurant for brunch. It was very popular, but probably a lot of work. He was semi-retired, so he had the time to do it. He did research to have talking points on the history of some spots we passed, like a tour guide.

It was a great low key meet up. You didn’t have to make friends with the organizer. If you were walking with someone you didn’t really like in the group, it was easy to drift to talk to someone else.