@svandorn, this is for you.
  1. Bourbon Trail
    I mean, this is both the obvious #1 and the deserved #1. Distillery tours in KY are second to none.
  2. Craft Breweries
    The craft beer scene in Lexington is only continuing to improve.
  3. Red River Gorge
    Incredibly beautiful geological area in the Appalachian foothills (and Daniel Boone National Forest) an hour east of Lexington with scenic views, awesome climbing and hiking, and the best pizza place in eastern KY.
  4. Kentucky Theater
    This is a movie theater in downtown Lexington that opened almost 100 years ago and plays art-house and limited-release films. The main screening room is incredible, but my favorite is a smaller screen on the side that's painted to look like a chalet in the mountains.
  5. Keeneland
    It's only open two months a year, but you can't spend April or October in Lexington without taking in some horse races. Just be prepared to feel mildly agoraphobic: There are only bigger crowds in town for UK basketball games.