I won a night in Cinderella's castle back on July 5-6, 2007. We were at Walt Disney World and my brother got off a ride and there were several members of the disney dream team waiting for us. They had us watch a DVD there, asked us if we ever had heard of the "Year of a Million Dreams" sweepstakes, and then told us our prize. After a bunch of signed paperwork and press releases and parents going through background checks, we were official winners

We won a night in the castle, dinner at the Royal Table (restaurant in the castle), VIP seating for the Magic Kingdom parade, a day in Magic Kingdom, priority on rides (we're talking a walk-on for Space Mountain!), and breakfast with the characters at The Crystal Palace the next day (restaurant in Magic Kingdom). I remember looking out the window late that night, seeing flashes of the cameras (through what i could see with the stained glass windows...unfortunately there aren't regular windows anywhere in the rooms...just stained glass) and thinking "wow! They're taking photos of where I'm sleeping tonight!"
We didn't have to enter anything...it's all random people chosen...for this prize, they choose one family out of all the parks...AM-A-ZING
Needless to say, I have a TON of photos (an entire album full just of the day with the prizes!)