Nov. 4 they will be running the Breeder's Cup (very famous horse race) at Churchilll Downs. Great time to be in Louisville or Lexington. Lexington will simulcast the race at Keeneland, which is worth a visit. Churchill tickets are probably easy to come by as well.

For food:

Cincinnati: If you like Itallian, Pompilio's in Newport, KY (across the river from Cincinnati) is a local favorite. There's also a place in Florence, KY near CVG called Karlos that the locals love.

Louisville: I think there's a great Irish bar/pub next door to the Hyatt in Louisville. Bardstown Road is the local hot spot for nightlife is Louisville. Also try Wick's Pizza, a popular local hangout.. There's also a great little French place at Bowman Field airport.

Lexington: A.P. Suggins is a local bar where, supposedly, lots of big-time business deals go down. They also have some of the best burgers in town. Cheapside Bar & Grill is a nearby favorite and there are a ton of other great local restaurants within walking distance of the Hyatt, many have menus posted outside. Avoid the clubs unless you feel like re-visiting your college frat days.

Columbus: I second German Village. Lots of great coffee shops and restaurants. Brewery district has lots of great places too. Spagio Wine Cellars has an attached restaurant that I've been curious about. Heard great things about Barcelona Restaurant too.

Enjoy your trip!