Oktoberfest is a blast in my book....if you are looking for New Years re-lived, then no it's not worth the drive. This weekend tends to bring out all the island residents, regulars, dock trash, and the likes. There is a nice size crowd, not to big and not to small. Perfect for mixing. The food is great, and I mean great. The music is polka, but there are still other bands at the bars. And most of them are open as well as most of the shops. A few are closed already, but most everything is still open, and sales galore. This is the time of year when you see things on the island that might turn your head...like Pat Dailey has been known to surprise the Roundy crowd with a little concert on stage with Mad Dog. (I have the pictures to prove it).
As for the weather, well it could go either way, normally it is pretty nice that weekend, however nasty weather can't be ruled out. So if you are coming to spend the day on the golf cart you might have a proplem, but if you are coming to enjoy the festivities and bars then who cares what the weather is doing!
Fall is a favorite time of year for regulars....fun parties, lot's of laughs and very social time. It is a great time to meet other "Bay Regulars" as fall weekends often bring out all the old school.
I say, give it a try...you can't beat the fall hotel rates. I think you'll have a ball...I know I will be having a blast.