Yeah, the fairs are boring, but that is mainly because there isn't anything else to do other than go to the pub. I sent Mavis there to chat with whoever she met to get her social need up; she lives alone with 2 chickens and hasn't entered anything in the fair yet.
I've decided to treat it more of a social event, (which is a large part of what they are irl anyway) and I figure if I want to win I'll bribe the Mayor. :* I usually don't notice what day it is in the game, anyway. ;) Whenever I decide to participate it would be a good way to introduce a bit of drama: get in a fight with another entrant, or sneak a kiss with someone so Mrs. Crumplebottom can strike. I just remembered, I haven't seen that yet!
I guess I could level one of the buildings near the village green and put some fun things to do in it, then go back and forth. yeah, there is a loading screen, but that might be worth considering.