[Travel Advice] Kentucky Bourbon Trail

Bourbon Trail for a long weekend

Clemens

Nov 15, 2025

Random Observation/Comment #906: I’ve accepted my vices. Brown liquor is on the top of that list.

//A casual bourbon trail haul

Things Kentucky Does Well

Kentucky Hugs - It burns so good and shows me such affection.
Fresh air - Rolling hills, crips mornings, and the sweet smell of fermentation barley.
Southern Hospitality - Every bartender is so kind to ask where you’re from and happy to share what their favorite bourbon is for the season/month/today.
Bourbon branding - There are so many nuances in making the bourbons, but the boom of its popularity was only around 2012. Every place has a schtick that’s pretty interesting to hear from their marketing department. It’s either all single barrel, finishing barrels, smaller batches for consistency, or some dude that is the Chief Whiskey Officer and has the best taste profile.

Things to do before visiting

Book your whiskey tastings and tours 2 months in advance - I think the tastings are worth the extra money. The good ones sell out fast.
For a less rushed experience, stick to a maximum of 2 tours/tastings per day - Starting at 10AM is really aggressive, but you’re 3 sips deep before lunch.
Book your Airbnb in the Lawerenceburg area - All the distilleries with the beautiful tours are not in downtown Louisville, but across the East to South of Louisville around an hour away.
Rent a car - There will definitely be some driving if you’re heading out to the actual distillery grounds. Just make sure you have a designated storyteller (I mean, driver).
Consider a guided full-day tour - The driver know the roads, the jokes, and secret spots.
Pack layers for November - We got some pretty surprising weather like a random day of snow.
Bring snacks and water - Hydration is key. I think we skipped lunch every day because we wanted more time for drinking. I suggest packing your own lunches or having a big breakfast and ending your day by 4PM for an early dinner.

Places We Visited

Airport free tasting? - This was unexpected and welcomed.

Mussel & Burger Bar - I think I would have preferred a burger over the mussels. The mussels were not overcooked, but I got a sandy one that turned me off to it. Sauce was great for dipping fries.

Bardstown Bourbon Company - Bar goals. I enjoyed their green label rye. I think I bought the very first one from their store.

Louisville Slugger Museum - A bit of an expensive 35 minute tour, but you get to touch some bats and ask some questions. It’s a nice break between drinking.

Art Eatables - Delicious, but overpriced chocolates. It’s great for a gift. They probably get a lot of good business because it’s a solid move to pair a whiskey with a fudge or chocolate.

Four Roses Distillery - Super easy tasting with a great bar. The angle for marketing is the single barrel 10 different combinations of blend and yeast. OESO was solid.

Whiskey Thief Distillery - Definitely my favorite stop. They only do 800 barrels a year, which is super surprising because they probably serve 10 of those barrels every few days. The 375ml thinner bottles are $80, but totally worth it. It’s always single barrel and you’ll never taste the same thing twice.

Castle & Key Distillery - Beautiful location with a legit castle filled with brewing equipment. I enjoyed the feeling of every tour being unique in walking paths and stories. I wasn’t crazy about the bourbon, but the rye and gin were very good. This is a fairly young distillery.

Woodford Reserve Distillery - I’m a sucker for a pretty estate. There’s a mini tour bus that brings you down to the few buildings to see the brewing process and keg storage. Lots of pretty photo opportunities. The original narrative is that Woodford is reliable and well blended to get the same result for mixing or a double oak for sipping. It’s weird that added a few other types in there.

Willet Distillery - Love the one pot still to rule them all. Very pretty grounds with the black warehouse looks. The progressive tasting method is a great way to keep the group engaged when they have to choose between tasting brands throughout.

Evergreen Liquors - This is more of a bar than a tour, but it has a lot of great options and the bartender Chrissy has great taste. Come here if you’re looking for something special and have some time to hang out. Wednesdays have half off pours!

Angels Envy Distillery - The narrative here is the finishing. I do appreciate an angel’s envy drink. The bar here has excellent cocktails, so definitely take time to hang out.

A summary:

@imseelemons