My local cycle club did a one-day ride in 2013. Here's their ridewithgps route, 50 miles and 3000 feet of rolling hills. It's a loop route from Frankfort KY.

From doing the Horsey Hundred ride (which is this weekend), I found the area has lots of smaller, rolling hills. Anywhere from 50 feet to 300 feet tall. There's often very little flat ground.

And I searched ridewithgps, "within 100 miles of Frankfort KY" keywords "bourbon trail":

This appears to be the long route from the Bourbon Trail page, with one end near Louisville, but I didn't compare it to the cue sheet: 177 miles

There are other distilleries in the area that aren't officially part of the Bourbon Trail. Search on Google Maps for "distillery"

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In Louisville:

Ride the "Big Four" bridge. It's a big railroad bridge, abandoned, with the approaches torn down in 1969! Now it has a cool spiral ramp. google map link

Ride 4 miles to Old Louisville, see the interesting architecture on the blocks near W Magnolia Ave and St James Court google map link

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Madison Indiana
If you are in the area, Madison is a nice town to visit. The historic part is below the hills, along the Ohio River, so all the sprawl and big box stores are up on the top of the hill.