DAY 1
Arrive and settle in
Head north to Shelbyville to stock up on groceries, beer and wine. If there’s time, stop at Jeptha Creed, a women-run, grain-to-glass distillery with a personal feel, or Bulleit Distilling Co. for its modern vibe and a Smoked Old Fashioned class. Evening at Cat Ridge: hot tub, sauna and a nightcap in the speakeasy.
DAY 2
Eastbound
Start easy at Four Roses, with its Spanish-style architecture and low-key tastings. Then Wild Turkey, perched above the Kentucky River, for bold pours and real bourbon history. Lunch and a stroll on Lawrenceburg’s Main Street, then finish with a glass at Rising Sons Winery.
DAY 3
Northeast
Woodford Reserve in the morning, one of the most beautiful settings on the trail, then Castle & Key, which feels more like an estate than a distillery (check their concert series). Lunch in Frankfort, and add Buffalo Trace if you have the energy; some call it the mecca of the trail.
DAY 4
Westbound
Jim Beam for historic rickhouses and a classic experience, then lunch at Bardstown Bourbon Company, home to one of the best distillery restaurants in the region. On the way back, stop in Bloomfield, a classic small town.
BEYOND BOURBON
More to explore
Keeneland and Churchill Downs for racing, Taylorsville Lake for boating and hikes, and antiquing in Midway.
