Apparently it’s Louisville. At least according to GQ, which may not be the most authoritative source on manliness.
Having spent a decade living in Louisville, ego prevents me from saying that it’s not a manly town.
What’s funny is that GQ recommends the following:
On the way out of town, hit one (or six) of the distilleries that flavor the countryside around Louisville. Our current favorite is Buffalo Trace, located in nearby Frankfort, Kentucky. If you road-tripped all the way to Louisville, as I did, now would be a good time to ask your girlfriend to take the wheel.
This seems to presume that you’re headed east out of town. I can say with some level of confidence that if I wanted advice on manliness, I would not travel east from Louisville. Still, Buffalo Trace is worth a stop.