Every now and then I book a road-trip on the whim. I usually have to plan because I don’t make enough money to spontaneously go on expensive trips but this time I had some available points for a car rental and two nights in a hotel. All using my lovely Chase Sapphire points by the way. Adding up the trip, as if I didn’t use points, the trip would have cost me around $400 just for the hotels and car rental alone.

The only downside was I had to get a rental car at Chicago Midway, which is pretty far from where I live. It took an hour just to get to the car rental but they are one of the few places where I can return a car at any hour. I got my car rental from Thrifty, and they actually get pretty great reviews. So with my ex in tow, we drove south through Indiana to Louisville, Kentucky.

To start off, I think next time I will invest in a standard rental instead of a compact. The compact was fuel-efficient but also somewhat noisy and the windshield wipers were flat-out terrible. But anyways the drive from Chicago to Louisville is not too far, around 5 hours, and that included a stop in Lafayette, Indiana. For people not from Indiana, that’s where the prestigious Purdue University is.

To be honest, it wasn’t the best weather to travel in. But I wasn’t expecting much since this in January, in the middle of winter, where grey skies and cooler weather are the norm. Actually, for most of the trip, the weather was fine. It was only the ride back where it was pretty dicey and I’ll cover that later.

Louisville

We arrived at 3 pm, put down our luggage at the downtown Aloft Hotel, and immediately went to go taste some bourbon. If you’re not familiar, Kentucky is famous for bourbon and there is only one real place to go to if you’re in Louisville; The Evan Williams Bourbon Experience. There are other bourbon distilleries to go to throughout Kentucky and there is even a Bourbon Trail, where people go to some or all of them to taste, but Evan Williams is one of the best in Kentucky. Also conveniently located right in the middle of downtown Louisville.

We opted for the bourbon tasting instead of the bourbon tour. It was slightly more expensive, $18 per person, but I wanted to taste the bourbon instead of learn about it. I can always read up online. The tour was totally worth it and probably the best thing we did in Kentucky.

First off, we were the only ones on the tour, being that it was right after the holidays in the middle of January. The tour started by taking us down a flight of stairs to a door that looks like a vault. The tour guide told us a set of words to say since this was an entrance of a “speakeasy.” In quotations because it’s actually not but it meant to seem like this was the 1920’s under prohibition and we had to ask to get in.

The guy acting and serving us bourbon was this older guy, I think named Jake. Really knowledgeable about Louisville and bourbon. What I learned is that Louisville and bourbon go hand in hand. Louisville was part of Bourbon county before it was split up way back when. Oh and bourbon is really just whiskey aged and made from corn. In fact bourbon is not bourbon if it’s not made from corn.

I also learned that the right bourbon is very good and goes down well. On the tour we tried 4 different types of bourbon and they all were great, beautifully colored, and highly intoxicating. The last one was aged for 23 years and sales for around $600 a bottle. In fact, they only sell it at the store and in Japan; apparently it’s really popular there. Overall the Evan Williams Bourbon Experience is well worth the time and money.

After the tour we decided to try some food at Mussel & Burger Bar 2. It got great reviews on Yelp and they had beer and cocktails, so sign me up. We also learned from our waitress how to once and for all pronounce Louisville. It’s luːəvəl, not looie. You can hear the pronunciation on the Louisville Wikipedia page.

Anyways the burgers and beers were amazing. We told ourselves that this is how you start a trip right, with booze and burgers. Tired, full and happy we retired ourselves to our lovely hotel after a quick walk up their famous 4th street. The street is really just entertainment and bars and since we didn’t feel like drinking anymore, we skipped it.

The next morning we get up early and head over to Wild Eggs, about two blocks down from the hotel to have a fantastic breakfast brunch. On the pricier side but on par with any breakfast I would have had in Chicago. Overall tasty and I would recommend it.

After breakfast we collect our belongings, get in our rental, and head over to Churchill Downs on the south side of Louisville. If you know anything about Louisville, this is perhaps the most famous local attraction and of course known for the Kentucky Derby. It’s a little pricey to get into but being that this is iconic place and I’m not in Louisville that often, I opted to pay the $15.

The museum is pretty nice and there are many exhibits to look out plus an amazing rotunda that plays an educational video. We got there early in the morning and since it was January, nobody was there. We toured the grounds for a bit, watched the video, and then jumped into the tour group to tour the rest of the grounds. The tour is part of the museum entrance ticket and was really the reason I wanted to go to Churchill Downs in the first place.

And the tour was worth it! We saw the signs of the past Derby winners and learned about the history of this historical venue; open since 1875. I also learned why I kept on seeing the name “Sir Barton” on signs and street names across Kentucky. He was a Triple Crown winner in 1919. We also got to see where they parade the horses, stall the horses, the real racetrack and some resident horses. The racetrack is gorgeous and well worth the $15 to get in. I learned how important Churchill Downs is to the state of Kentucky and the prestige it brings.

Frankfort

We got in our car and headed east towards Frankfort, the capital of Kentucky, only about an hour outside of Louisville. Driving is a little intense since the city has hills surrounding it on all sides. You come in steep. However I found it beautiful and loved this tiny capital city.

My first impressions were not favorable. Like a lot of Kentucky, poverty was everywhere and always clear. And about the only thing to do in Frankfort is visit the State Capitol and Governors Mansion and is easily the most biggest structure in the city.

We parked out car right in front of the Capitol building and took some pictures out front before attempting to get into the building. It wasn’t open so we walked over to take pictures of the beautiful Governors Mansion before hitting the road towards Lexington. Frankfort is worth a visit if you’re in the area but only for a couple of hours. The city is strictly a governmental setting and there is more to offer in nearby Lexington.

Lexington

While grabbing some Starbucks we headed southwest for 30 minutes to Lexington. Deciding that we were hungry we took a detour and headed to the western part of Lexington to this middle eastern restaurant called Sahara Mediterranean. Near the esteemed University of Kentucky, this place was packed with students and other patrons, a good sign that this was a legitimate restaurant to eat at. I’ll tell you, if you want great places to eat, try Yelp or TripAdvisor. Lately they haven’t received the best reviews (scandals involving fixing reviews), but I still think that they will guide me in the right direction. I’m all about more healthy authentic places when eating.

We wanted to see if Lexington was worth the stay, if this was the right city to come to! We drove through Downtown Lexington, you know to scope it out, and it did look charming. We drove past downtown, to the east part of Lexington, to drop off our luggage, freshen up and then head back to downtown to explore.

Lexington is charming but to be honest, there isn’t much to do. Yes we saw the outside of the opera and yes there is a shopping center, but that’s about it. However Lexington has that quaint southern city feel and the architecture to gleam over. Outside there was this place called Keeneland that would have been so worth it if we had time. We drove past it and it looked beautiful.

One thing that we wanted to do at Churchill Downs was to sip on a Mint Julep however their café wasn’t open. So in Lexington we tried to find a place that sold Mint Juleps. You might thing this is easy to find but most bars in Kentucky don’t advertise that they sell them (I think they should). So I looked up what essentially a Mint Julep is and it’s simply sugar, bourbon, ice and mint.

So walked over to a bar called Shakespeare and Company, and found a Mint Julep recipe on the menu. They just called it “Cold Comfort.” And now I have new appreciation for bourbon! If the tasting in Louisville didn’t convince me already, bourbon with the right ingredients is absolutely fantastic. Bourbon is strong so you don’t need that much to start feeling a buzz.

After our Mint Juleps and dessert we headed back on the road, west of Lexington towards Versailles, Kentucky. I think this is actually a great place to focus your energy, if you’re traveling in Kentucky. To stay outside of the cities and tour the countryside. It’s filled with rolling green fields, with horses and beautiful southern architecture. That’s where I found most of my joy while in Kentucky and it was fun to drive among.

Versailles is a nothing town so we drove straight out of there and followed signs to the Woodford Reserve Distillery northwest of the city center. This distillery is part of the bourbon trail, meaning a recognized distillery in Kentucky. It’s actually closer to Frankfort and looking back on a map, I’m surprised we drove so far back to the west.

We didn’t have time to go inside but the drive around was beautiful and that was enough for me. We stopped along the way to take photos and just enjoy the countryside; not like there was much back in Lexington anyways.

Kentucky

That was it. After visiting the distillery we grabbed some food and went back to the hotel to watch movies. Can’t see much at night and we already had enough alcohol for a weekend. Our goal was to get up and slowly get back to Chicago on Sunday. Little did I know that the weather would be so crappy.

Kentucky, for me, is a state I would return to. It’s beautiful, the people are generally welcoming, and has a lot to offer. It’s like a southern state with amazing food, people who speak with a drawl, and a more slow-paced society. A nice change of pace from Chicago. And yeah I didn’t get to see too much but this weekend was a good start to get a glimpse of Kentucky. Perhaps I should come in the summer next time?

Ohio and Indiana

Weather came through that Saturday night and Sunday morning and temperatures dropped 20 – 30 degrees all across Illinois, Indiana, Ohio and Kentucky. Flurries, ice, snow and blizzard conditions effected much of the roads at night and it only lightly cleared during the day. On top of that my car rental ran out of wiper fluids. It was not how I wanted to drive back and ice covered most of the road from Lexington to Cincinnati, Ohio. I never felt so good to get off the road as when I drove up to Cincinnati, which I have to say is a very lovely city.

After filling up or tea and lunch in Cinci and wiping off dirt off my windshield with hot tea (yeah no joke), we headed into Indiana which to put it bluntly, was a mess. Cars spun out everywhere, accidents on the road, and just a thick amount of ice on all parts of the road. Throw in wind and snow; it was stressful.

This was probably the only time where I thought I would get into trouble. The last 10 miles into Indianapolis were the absolute worse and it was only after getting off of I-74 did the driving conditions improve drastically. I won’t do that again and I wouldn’t have gone on this road trip if I knew what it was going to be like that.

Never was I ready to get back to Chicago and be home. Overall the trip was fun and just the right amount of time for a quick weekend to explore something new. I would do it again and I’m happy I went.

images by: shawnvoyage