If you live in the DC area and want to enjoy some good wine and help a good cause, I suggest attending the Blind Wine Tasting of Old Town. Tickets are $50 a piece and you will get to sample wine from local wineries and food from local restaurants. A friend of mine attended this event last year and said it was a lot of fun and pretty casual -- which is good, because I hate wearing a tie :).

Best of all, you can help a really good organization.