Katie, are you sure about the pledge thing? I entered last year and it took my zip code, although I *might* be on the edge of what is considered "greater Boston." It does kind of s*ck, though. They did have leaders for rides into Boston from as far west as Stow last year, and I don't think anyone came! I wanted to lead a group out toward Hudson, where I worked, but there was no support for that.
I did manage to get a group of 5 people to go on an 8 mile after work ride with me, during Bike Work last year. But, it did take a whole lot of organizing and wrangling.