I volunteered at the Boston Book Festival last year -- it's a sweet event, reminding me of literary festivals in Buenos Aires.  If you haven't been before, consider going - this year it will be on Saturday, Oct 15.  Last year we didn't plan any sort of Wikipedian gathering around the festival, but it would have been a fine opportunity.

The crowd is an interesting mix of authors, publishers, and educators.  Groups like OLPC and 826 Valencia tend to get tents on the plaza for the event, and many local authors are looking into new publishing models and other ways to share stories and knowledge.  As we get better at outreach, this might be a good place to attract that crowd to work through & with Wikipedia and sister projects.

The festival is supported and run by the local community -- they recruit volunteers every summer, and this month the Media Lab is sponsoring a fundraising dinner for them.  Volunteering is a great way to meet the presenters; and the dinner looks pricey but fabulous.  Check it out if you are interested: