I'm not a people person or organizer, but I've thought Salem Common would be a great place to have a bike show, maybe classics from different eras and categories (if enough show up) and a custom section, maybe voting for a few categories of awards. Salem is a college town, historic Salem Common is very visible and gets a lot of tourists and resident traffic, it's about a mile from the train station, and they host a bicycle race there in the fall. I think a focus on swap meets makes the event more of an "in-crowd" kind of thing that pushes away the normals, which is what I think most of us would want to avoid. I'm not saying a not to have booths, but I think it would be more appealing to the general public to emphasize more general appeal bikes, like customs, bright colored ballooners, and antiques like high wheelers and hobby horses (if we can get them to show) to show the evolution of the bicycle and the fun aspects. Speaking of history, the PEM is two blocks away and, at that, perhaps the Essex St. pedestrian way running along its facade across from the fountain would be another option.
I was thinking of doing one of those tweed rides with my ex this year, but the calendar still has question marks for the exact date sometime in April, while everything else on the vintage calendar has an full date, so it doesn't look like it will happen.