Kentucky Derby Trip + Bourbon Trail

Kentucky Derby Trip + Bourbon Trail

Sean and I just got back from a 4 day trip to Kentucky. It’s been on our bucket list to go to the Kentucky Derby and now we can happily cross that off our list! Happy that we went and experienced it but sad that it is now over. I would absolutely go back and I know Sean would too. He loved the gambling and betting on the track and surprisingly enjoyed getting dressed up. Today I’m sharing our trip to the Derby, I hope you enjoy!

Where we stayed / how we got there

We drove down to Kentucky with good friends of ours in their RV. The RV can sleep 6 comfortably but it was just the 4 of us so there was plenty of room to move around. If you have a chance to vacation and travel in an RV, you should. It’s such a fun way to go. There is a campground close to the track that accommodates large RV’s and that is where we parked for a couple days. To get around town we called Uber or Lyft which made it so easy.
Louisville also had Bird and Lime scooters to rent which were all over the city. They are such a fun way to get around.
There are a ton of VRBO and airbnb rentals all over the area. If you are planning to go, book early. They jack up prices closer to the event. Hotels are also an option but house shares are the cheaper route.

The Derby

If you are not familiar with the Kentucky Derby it is a horse race held in Louisville, Kentucky. The Derby is a “Grade I stakes race for three-year-old Thoroughbreds at a distance of one and a quarter miles at Churchill Downs” The purse this year was a record high at 3 million. You can read more about the history here. Churchill Downs is such a sight to see. It stands bright white and gold in the middle of a neighborhood. We didn’t get to see everything because it is so huge. We will need to plan a second trip just to see everything.
You can get tickets for the 2 days or just 1 if you prefer. We attended both the Oaks and the Derby. We got tickets in the grandstands, in the front row, right on the track for the Oaks which I would recommend. It is such a better way to watch the races. We purchased general admission in the infield for Derby day, which is standing room only, for just $60 a person. Tickets can soar into the thousands depending on which level you choose to watch the races from. There are also suites available.
You learn so much about betting and traditions while at the Derby. My husband and I placed quite a few bets and lost. Horse betting is hard and unpredictable.
To follow tradition we ordered Mint Juleps and lilies. You get your drinks in commemorative glasses to take home.
If you watched the Derby then I’m sure you witnessed the winner get disqualified. Who knew that the 145th Kentucky Derby would make history with the first ever disqualification and we were there!

Churchill Downs

The outfits

Oaks day is pink to bring awareness and raise money for women’s health. I picked out the brightest pink I could find which was this jumpsuit from Express. It was on sale when I bought it too making it very affordable. I sized down for a better fit. I’m 5’7″ and I should have gotten this hemmed but ran out of time. I wanted a crop leg look and it hit just above my ankles. I would have liked it shorter.
You guys remember my shoes from JustFab. I shared them in stories and they’re the best shoes to walk around in all day. So comfortable. They went perfectly with the white hat that I’ve had for years. Purse is Walmart and Jewelry is Kendra Scott.

Kentucky Oaks

I was so excited to look for my dress. I ended up purchasing my Derby dress from Lulus. I needed to size down for a better fit. I love the classy vibe and all the cut outs of this dress. This dress also comes in other colors. It’s a thicker material but wears very comfortably.
My fascinator was from Pippa and Pearl on Etsy and I just LOVE it. The quality is great and there is such an attention to detail. I do not typically wear blue so I wanted to step out of my norm and go bold. I love the mesh on it because it reminded me of my wedding day. : )
I wanted all my accessories to be light blue and let me tell you that was a hassle! I ended up finding the perfect shoes at DSW in the right color. Fit is TTS.
I found my earrings at Kohl’s but I could not find them online.
I would have gotten more photos of my dress but it was pouring rain all day long!


Bourbon Trail

The bourbon trail is all over Kentucky and Tennessee. We drove an hour east towards Lexington to the Buffalo Trace Distillery. It is located in Frankfort and is one of the oldest running distilleries in the area. The grounds are so large and the tour is free. You also get a tasting at the end of your tour which includes 5 different spirits.

Buffalo TraceBuffalo Trace

On our way back home we stopped at the 450 North Brewing Co. in Columbus Indiana for a drink and some lunch. This brewery is not part of the bourbon trail. The brewery also has the Simmons winery on the property. They have a beautiful outdoor patio area where we sat and enjoyed a drink. The beers were all so delicious and the food was amazing. I recommend stopping here. The slushy beer was one that I have never heard of before but it is so good!

450 North Brewing450 North BrewingIMG_5798

Thank you all so much for reading. Until next time,


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  1. October 20, 2019 / 9:17 am

    OMG this place looks very beautiful and also love your outfits <3

    • October 21, 2019 / 3:52 pm

      It was beautiful. One of the oldest distilleries in the area. Thanks so much!

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