Every other year, UMass Lowell in Lowell, MA (Jack's hometown) holds The Jack Kerouac Conference on Beat Literature. The next conference is scheduled for the first Thursday and Friday in October 2009. Here's the website. I contacted Professor Holladay. She didn't provide me with any additional information, but did encourage me to submit a proposal.
October is the annual Lowell Celebrates Kerouac! festival, and I haven't been able to confirm a date for that. However, I don't think the two events will interfere with each other.
Yup! That could mean two weekends in Lowell this October.