hmm... let's see, we have done the "Rubber Duck Regatta" where people pay $10 for a numbered rubber duck, which are then released into a lake, and the duck that crosses the finish line first wins (1/2 or 1/3 of the total pot). Nice because you can reuse the ducks every year. We mix this with a BYOB (bring your own basket) picnic and run a silent auction and other little fair type booths (face painting, small games, bake sale, yadda yadda). At Christmas (actually, we started around September) we asked families to donate a christmas cookie recipe and printed a spiral bound cookbook (all done at Kinkos) that we sold through the school, and some parents brought them to church, work, etc. We also had kids design christmas cards in Art class and a local printer gave us a very good deal so we had the top ten designs made into cards and sold those through the PTA and school website (also got some press for that one, so a good number of community sales as well). Monte Carlo night was always a big draw, I've never been to another one, but ours went like this. Each family bought a set amount of "play money" (1 real dollar for 5 dollars play) and then used that to buy into the games. (on average, $20 per person to $100 per person). At the end of the night, all the play money was converted to raffle tickets instead of real cash, and local businesses donated goods and services to raffle. We had everything from dinners and haircuts to vacations, TVs and even a car! We set up boxes for the individual raffles and held them at the end of the night. Also, since we weren't using real money, the kids could participate and we had games set up for them, like Turtle races (bet on the fastest turtle, loads of fun) and one of those machines that blows play money around while the kids grab it (best for the older kids). And other fun games with no play money involved (go fish tournament, stuff like that.) A local restaraunt donated catering services so we had a couple of classrooms set up like a cafe.
Anyway, those are some of the things we did. Oh, wait, we also put in a vending machine in the teacher's lounge that sold bottled water with a custom label that we acquired from GFS specifically for fundraising. We also sold the water at all of the events the school had.