If you are in the Cleveland area on August 7-8, 2009 I highly recommend checking out the Vintage Ohio wine festival.
It's one of the biggest wine festivals of the year with dozens of Ohio vineyards representing their product. It costs $22 in advance or $25 day of for essentially unlimited samples (the past few years we've got a card for 81 or so spots, which never get filled entirely) of any wine you'd like. In the admission is the wine samples, a free embossed glass, and some small food items from various vendors (my personal favorite is the balsalmic vinegar stand).
I recommend getting there early to avoid the heat and the lines. The last thing you'd want is to have 30 samples in you and waiting 10+ minutes to get another in the heat.
I wont be going this year since I'll be in Egypt, but my family is going. If anyone is in the area it is definitely a good weekend activity.