I looked into driving back on January, it is possible, and it could be made into an event, but it is late to organise now. The idea would be to take a minibus, or a couple or three cars, stop and meet local Wikimedians every day, collect photos for Commons, use mobile technology to blog and edit on the way.
The train does sound like an adventure, but very limited freedom for diverting a couple of miles for an event or landmark.