The gf and I had a good experience a few weekends back at Equus Run. Only really offered one bottle I was thrilled with (think it was the Cab), but I go mostly for the experience, not expecting winery genius. Take a basic picnic with you, and you can eat it on the theater stage overlooking Elkhorn Creek. Good picnic location, as you don't need to pack and carry a blanket. Our tour guide was exceptional, although he did have a super soft voice.
Midway's a nice little town too, although some of the shops were more corporate and less "unique" than I expected. We had a nice snack at a place on the main drag. Can't really remember the name of the place, but it's right above a used bookstore. We ordered off the dessert menu. Although their were eight choices, both of us chose the jam cake. I'm glad they did not include the nutritional info with the cake, as you could taste the excessive (but palate rewarding) brown sugar in each bite. Fresh press-pot coffee too.
I'd like to go back and eat here:
http://heirloommidway.com/.
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FWIW, I used this website to help plan the trip:
http://www.kentuckytourism.com/interestfinder.htm. I've only used the site this one time so far, but seems the gov't has made something good here.
The way I used it was:
1. Search for "Wine" in all cities
2. Once I found wineries that interested me, I then searched for "All Interests" in the city in which a specific winery is located.
That approach allowed us to make a day out of it, instead of just picking a winery. We had plans to make "Lovers Leap" in Lawrenceburg, but I guess we spent too much time over that jam cake.
Thinks the frosty mug is the low point in American history.