One-week Kentucky Bourbon Trail road trip itinerary
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There’s no drink that’s quite so quintessentially American as bourbon.
Born in what later became the Commonwealth of Kentucky in the late 19th century, it was declared America’s Native Spirit by Congress in 1964.
More than a hundred years on, this corn-based American whiskey is still one of the most popular spirits in the USA.
The best way to experience this slice of Americana? The Kentucky Bourbon Trail.
It highlights close to 50 distilleries where guided tours and tastings delve into bourbon’s historical and cultural significance.
Just make sure you’re over 21, the legal drinking age in the US, and have a photo ID for proof.
But there’s so much more to do in the Bluegrass State beyond distillery hopping – so here’s how to make the most of your bourbon-inspired road trip.
How to do the Kentucky Bourbon Trail
As I mentioned, the best way to explore the Kentucky Bourbon Trail is on a multi-city road trip.
Having been to all of the main cities, I think the three best stops to make your base are Louisville, Lexington and Cincy (Cincinnati, Covington and Newport).
They offer the most to do, and you can visit them on a more or less linear route.
In terms of timings, you’ll want to allow for at least a week to 10 days to see Kentucky at a leisurely pace.
And aim for September – this is when most of the bourbon festivals and events are taking place.
First stop: Louisville
You’ll want to spend at least two or three days in Louisville.
What to do in Louisville
Start your journey at the Frazier Kentucky History Museum on Museum Row (W Main Street) where you can explore exhibits on how the whiskey is made and stir up your very own Old Fashioned as part of its signature cocktail experience.
Afterwards, stroll over to the Evan Williams Bourbon Experience for your first distillery tour and tasting.
Also within striking distance is the Louisville Slugger Museum & Factory, where you can hold Babe Ruth’s baseball bat, and the Muhammad Ali Center, which showcases the champion boxer’s life and legacy.
There are some lovely old homes in Louisville – and this tour of Old Louisville* is a good overview of that area and the city’s history.
Be sure to set aside a day to visit Churchill Downs, home of the historic Kentucky Derby.
Bourbon-infused mint juleps are de rigueur when over 150,000 people descend on the track on big race days, but otherwise stop by the Kentucky Derby Museum for a fascinating behind the scenes tour.
Finally, if you want to visit some of the out of town distilleries, consider booking this bourbon tasting tour*, which includes several guided tours and tastings as well as pick up from your hotel.
Day trips from Louisville
There are two cities that are worth a day trip from Louisville if you’re keen to stay in one spot rather than move to a new hotel every night.
Bardstown bills itself as the bourbon capital of the world.
It’s got a quaint Old World vibe, and hosts the Kentucky Bourbon Festival each September.
And then there’s Frankfort, home to Buffalo Trace, one of the oldest distilleries in Kentucky.
It’s not officially on the trail but it’s well worth a visit – and tours and tastings are free, though it needs to be booked ahead.
The most interesting option is the Old Taylor Tour, which takes you to see the remnants of the O.F.C. distillery by the Kentucky river.
Where to eat in Louisville
Doc Crow’s on the very aptly-named Whiskey Row (E Main Street) does a mean line of Southern barbecue and boozy desserts but it’s the extensive whiskey selection that impresses the most.
There are over 2,500 bourbons alone, only a small selection of which are on display in the bar.
This much-loved barbecue restaurant is part of Louisville’s free Urban Bourbon Trail, which offers discounts across selected bourbon-loving venues.
Where to stay in Louisville
The Grady Hotel* is conveniently located on Museum Row, and their speakeasy-style basement bar, Wild Swann, does a killer espresso Old Fashioned.
Down the road, the 21c Museum Hotel Louisville* is another fun spot, with an art gallery in its lobby.
Second stop: Lexington
A day or two is enough for the highlights of Lexington.
What to do in Lexington
Some of the most prized race horses in the world are bred and stabled in Lexington.
A handful offer tours by appointment, such as Godolphin’s Jonabell Farm, home to Kentucky Derby winners Street Sense and Nyquist.
But it might be easier and cheaper to book a guided tour, such as this half day visit to a thoroughbred horse farm*.
In Lexington, most of the bourbon action is clustered around the Lexington Distillery District, a buzzy spot with bars, restaurants, live music venue The Burl and a few different distilleries.
Of the distillers, the most famous of the lot is the James E. Pepper Distillery.
The National History Landmark was originally built in 1879, abandoned for some 50 years, and then revived in 2018. Tours are available and should be pre-booked.
You can also book a food and history tour* of the area that includes lunch and tastings.
Where to eat in Lexington
Goodfellas Pizzeria in the Lexington Distillery District does enormous New York-style slices to soak up the alcohol.
For a sit-down affair, book a table at Lockbox for dishes like roasted pork belly with black olive oil and fennel honey served in a former downtown bank.
Both have stellar bourbon lists.
Where to stay in Lexington
Boutique hotel The Manchester*, with bourbon-inspired interiors, is just a short stroll from the Lexington Distillery District.
Third stop: Cincy
Cincy is the nickname given to the three cities – Covington, Newport and Cincinnati – that cluster around the Ohio river.
There’s plenty to do here, so budget for at least three days.
What to do in Cincy
In Covington, there are two essential bourbon experiences.
At Wenzel Whiskey, you can try your hand at blending whiskies, while just a block away is Revival Vintage Bottle Shop where you can taste vintage bourbon and other spirits from just $5.
Newport is home to New Riff, where you can taste bourbon straight from the barrel.
Also worth doing is the gangster-themed walking tour* – this city had at one time been run by the mob.
Cincinnati is right across the Ohio river from Covington. Baseball, American football and soccer are all big business here so catch a game if you can.
Where to eat in Cincy
Skyline Chili in Cincinnati is the place to try the three-way, the fast food staple where spaghetti is smothered in layers of chili con carne and cheese.
On the Kentucky side, Libby’s Southern Comfort in Covington does generous portions of Southern classics.
Think fried green tomatoes and hush puppies, washed down with the incredibly moreish Libby’s cheerwine bourbon slush.
Where to stay in Cincy
Stay at Hotel Covington* and you’ll be able to get to pretty much everywhere on foot.
How to get to Kentucky
Flying into Louisville Muhammad Ali International Airport (SDF) is the obvious choice since the Frazier Kentucky History Museum in Louisville is the official start of the Kentucky Bourbon Trail.
The trail is very much about building your own itinerary, so there’s no formal end of the trail – you could do a circular loop, for example.
That said, if you’re planning to do a linear route then Covington is a good place to finish. Cincinnati/Northern Kentucky International Airport (CVG) is the nearest airport here.
For those travelling from the UK, doing the route in reverse (from Cincy to Louisville) would make the most sense as British Airways* flies to CVG direct from London, which vastly reduces flight times.
Renting a hire car in Kentucky
There are several car hire companies at Louisville Muhammad Ali International Airport, including Avis*, Enterprise*, Hertz*, and National*.
You can also pick up your hire car in the city.
Louisville has decent public transport as well as Uber if you want to pick up your car later.
Make sure you have a designated driver for this route if you’re not signing up for a tour.
Kentucky’s legal driving limit is a blood alcohol content of 0.08 per cent – anything above this and you’re breaking the law.
Tips for EV drivers
This route is really easy to do in an electric car too.
There are plenty of charging points in the bigger cities, and there’s rarely more than 100 miles between them.
The one exception is Covington where EV charging points are still scarce – but you only need to cross the river to Cincinnati and you’ll have access to over 1,000 charging stations.
What to pack for Kentucky
Casual outfits are fine for most places in Kentucky, though you’ll want to dress up for dinner.
During the summer months, stock up on sunscreen and insect repellent.
My ultimate packing list is a great guide to what else to take.
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