Bluegrass and bourbon: my Chicago and Kentucky holiday

Why Kentucky?

Kentucky isn’t very well known in the UK as a huge tourist destination, but I hope that reading this blog will change that for you. Tucked neatly between Tennessee and Ohio, this beautiful little state is home to friendly locals, prize-winning thoroughbred horses, tiny distilleries producing sensational bourbon, green pastures, twinkling low-key cities, the famous hot brown sandwich and incredible pieces of US history.

How to get there

There are 2 international airports in Kentucky so you could fly into Cincinnati/Covington Airport in the north or directly into the capital of Louisville. However, if you want to road trip across the state, as well as combine it with some of their great neighbours then I’d recommend flying into Nashville or Memphis and exploring Tennessee first before driving through Kentucky. If you want an even longer road trip, then our Chicago to New Orleans road trip heads right through Kentucky, taking in the best of this beautiful state. I started my trip in Nashville, which I talk about more in my Nashville blog.

Bardstown

Driving up from Nashville we headed to Bardstown, a lovely little spot about 45 minutes outside of Louisville. This is the heart of Bourbon country. Bourbon is different from whiskey in that it must have at least 51% corn in the mash. Almost all bourbon is made in Kentucky and the locals are proud of their world-famous tipple. In Bardstown, we stayed in a lovely little guest house called Talbott Inn, right on the courthouse square and right next to the Old Talbott Tavern. The rooms were lovely and boutique, very modern considering how old the building was.

Our first stop in Bardstown was the Oscar Getz Museum of Whiskey History. I wasn't really sure how much history there could be about history - but boy was I wrong! It was a brilliant little museum, with lots of information about the Prohibition era, the reasons it was passed into law and how the public reacted to it. The museum has original posters protesting and proclaiming prohibition, as well as moonshine bottles and exhibits on Abraham Lincoln and George Washington. 

Bourbon Country

I spent the next few days taking in the best of Kentucky’s bourbon scene around Bardstown. I would really recommend visiting a few different distilleries – they are all so different. Even if you don’t like drinking neat bourbon, it’s a fascinating area to explore and you can always enjoy bourbon with ginger beer, in an Old Fashioned or even as Bourbon Cream (similar to Baileys). My favourites were the Willett Distillery, LUX Row and Buffalo Trace.

The Willett Distillery is a small family-owned farm, producing a small amount of beautiful bourbon. It was such a gloomy December day when I visited and it was still such a lovely spot – with mistletoe growing in the trees and the owner's wife showing us the process of turning corn into bourbon. LUX Row was more modern, a new building but with a brilliant tour that explained the art of creating the perfect bourbon.

My favourite spot at each distillery was the storage of the bourbon barrels. These huge warehouses are usually 4 or 5 floors high and have a skeleton of bars and girders holding all the barrels in place - you can see right up inside them, where the barrels have been resting for sometimes over 25 years. It's an amazing sight.

Buffalo Trace Distillery

In contrast to the smaller, family-owned places, Buffalo Trace is a huge operation and one of the very few distilleries that date back to before prohibition. They managed to keep going during those 14 years as they were one of very few companies to receive a permit to bottle medicinal whiskey.

Despite its size, it has a nice warm atmosphere – we were shown around by a man named Freddie, the third generation in his family to work at Buffalo Trace. We watched the barrels be rolled between buildings, learnt about the famous Blanton’s Bourbon and even got to hammer in the stopper into a barrel! I bought a big bottle of bourbon at the end of the tour and have such wonderful memories when I reach for a glass at home.

Horse Country

Getting closer to Lexington, we started driving past large green fields, with dark horses grazing peacefully behind the black fences. We took a tour of Airdrie Stud, a horse farm that breeds some of the best of Kentucky’s thoroughbreds. It was wonderful to meet the horses, they are such impressive animals but still so friendly, with lovely soft noses. Horses are such a huge part of Kentucky, so a horse farm tour is a must-do activity.

Louisville

Heading to the largest city of Louisville, I’d recommend visiting the Kentucky Derby Museum, where you can learn about the extraordinary experience of this world-famous horserace as well as meeting their resident thoroughbred. After that, you can head to Churchill Downs, where the race takes place, before driving to Frankfort Avenue, the road that connects the city’s most charming historic neighbourhoods. It’s the perfect place to grab a ‘hot brown’ for lunch – a Louisville classic open sandwich made of turkey, mornay sauce and cheese – trust me, it’s delicious! We spent the afternoon exploring the city a little before hitting a bar to listen to some live bluegrass.

Covington and Cincinnati

Leaving Louisville behind, we headed north to Covington, the northernmost city in Kentucky. Covington sits right on the Ohio River, just over the water from the big city Cincinnati. The food here has a real German flair to it, thanks to the strong German heritage in the area – we ate plenty of pretzels and sauerkraut with beer here. This was a lovely end to our time in Kentucky – we went to a cool speakeasy bar to taste even more bourbon (I think I was an expert by this point!)

Just over the bridge is the great city of Cincinnati, Ohio, somewhere I knew very little about but was excited to explore. There is a brilliant market downtown, the Findlay Market, full of boutiques and local food producers. It’s the perfect place to explore for a couple of hours before catching a football game – the Cincinnati Bengals are the local team. You can’t visit without trying their famous dish - Cincinnati chilli. This dish is very simple but so tasty – you can have the original 3 way chili (chili, spaghetti and cheese), 4 way chili (plus onions) or 5 way chili (plus beans). The amount of cheese they put on top is outrageous but it’s all part of the charm!

If you visit then I’d recommend you stay in Covington but visit Cincinnati for the day – Covington feels like a cosy neighbourhood of the bigger city. I stayed at Hotel Covington; it is a modern and stylish hotel with enormous rooms and the comfiest beds. I really recommend it.

Chicago

After my great road trip through Kentucky, I flew from Cincinnati to Chicago to have a few nights in the windy city before I flew home. Winter is a magical time to visit Chicago, but you need to wrap up warm as it can very cold! In fact, when I landed in Chicago it had just started to snow but, determined to explore the city as much as possible I pulled on my woolly hat and headed out into the streets. First, I went to see the famous Cloud Gate, more commonly known as the Bean. It was so incredible – and so big – close up. I was lucky as the cold weather and snow was clearly putting off other visitors and I got the bean all to myself.

Next, I headed to the Art Institute of Chicago, where I had been looking forward to wandering the halls. I actually really love visiting museums alone – you can go at your own pace and, I think, discover a lot more, as you pause wherever you want and don’t feel hurried. The famous ‘American Gothic’ painting by Grant Wood and ‘The Bedroom’ by Van Gogh, were my favourite. For dinner, I headed to Lou Malnati’s to indulge in a classic deep dish pizza!

The next day I explored even further – I did an architecture tour of the city, learning about the amazing buildings that make up Chicago. I think the architecture here is some of the most impressive I’ve ever seen in the USA. I also headed to a beautiful Christmas market, full of hand-made German ornaments and sugary, cinnamon doughnuts. I finished my evening at the comedy club, ‘The Second City’, where Tina Fey and Steve Carrell are just two of their esteemed alumni. A night of chicken wings, beer and hilarious improv comedy was the perfect end to my trip.

Inspired to visit beautiful Kentucky?

I think you can tell from this blog how much I enjoyed my trip to Kentucky and Chicago. It’s a fascinating and pretty little corner of the USA and perfect for exploring if you love food, history and bourbon. If you would like to plan a trip to Kentucky, give us a call on 1273 320 580 or request a quote. We are experts in planning tailor-made holidays and round the world flights, so we can work together with you until we’ve created your perfect trip.