Drink bourbon, watch hoops, and bet on the ponies in Kentucky
Distance from Chicago: 373 miles southeast, six-hour drive
Why it made our list: An epic trinity of southern delights awaits starting at Rupp Arena, which explodes in a sea of loud blue madness most Saturdays in the fall as the Kentucky Wildcats make yet another bid for a national title. Another high point is the Kentucky Bourbon Trail, where you can watch bottles being dipped in red wax at the Maker’s Mark Distillery (and, of course, sample them in the tasting room). But no trip would be complete without a visit to the legendary Churchill Downs, where racing season runs through November 29.
Side trip: On the way there (or back), stop by the equally cool town of Louisville, which is overflowing with cool places to eat and drink. Handily, the Kentucky Bourbon Trail takes you right there.