What about a jousting tournament, or perhaps a competitive celebration involving several different types of events that different characters can join and compete in? Something like the Olympics?
Also, maybe have a formal evening in a casino type of setting? There could be live performances, dancing, drinking, and lots and lots of gambling and games for fun. Lots of stuff could happen, and lots of twists! The poor could become rich, and the rich could become poor! You never know.
I'm also a fan of the idea involving performing artist characters--I think that would be fun for all.