A few friends and I take a trip once or twice a year together (we were all roommates in/after college).

Usually, we go on a wine trip, to Napa or the Willamette Valley. In fact, the Willamette is our favorite destination. We have done non-wine trips but it always seems to rain when we do...

In any case, we're trying to figure out where to go this year. Portland OR is a little far for me, and another of us is expecting a baby shortly after the proposed trip at the end of Sept so he doesn't want to be too far for too long from his wife.

One of us is a bona fide wine connoisseur with an 8000 bottle cellar who always wants to go on a wine trip. He can be convinced to do otherwise, as long as there are nice restaurants with respectable-to-him wine lists. He suggested Blackberry Farm in Tennessee, but it's ludicrously expensive.

We would like to go somewhere rural or semi-rural with outdoor activities (hiking, golf, perhaps something boat related). In the past, we've gone to Shelbourne Farm in Vermont (it's a contender for a repeat), Lake Geneva WI. Can people suggest a resort or rural area with good restaurants and nice outdoor activities that is doable for a weekend from Chicago or the east coast?

Thanks