So it's looking like the weekend that I was thinking about doing the meet and greet there will be the Midwest Overland Society's Northwoods Rendezvous. Absolutely anyone can go (I'm hoping to try, but with it being right before a trip I'm not sure I'll be able to make it). I will post more information as I get it, and will make an event page about it after I get back from my trip this weekend.
Usually it's pretty low key, with trail rides Friday night, and all day Saturday and generally a cooking competition if you decide to participate in it. It's usually in the Foothills State Forest, and stay around Backus. You will get pinstripes if you do the trail ride, but it's not an overly difficult trail.