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.