Kentucky Derby Weekend – Part One.

I’m just back from what may have been one of my favorite press trips ever. Press trips are tricky. We’ve talked about them before (and why I say no most of the time). In theory, they sound all glamorous and amazing – like a free vacation! But they usually end up being stressful. I’ve been on press trips where we are literally in activities from 8am til midnight, all the while expected to create beautiful content that we (ideally) post in real time. There’s no time to actually work and I wind up working late into the night. I usually come home tired, cranky, and way behind on everything. At the end of the day, I’d rather just travel less frequently but on my own dime.

This is all making me sound like a super fun person but I wanted to give you a little context as to why this weekend was so much fun. When the Vineyard Vines team reached out to invite me to The Kentucky Derby, I actually let out a (small) squeal at my desk. I have always dreamed of going to The Derby but never actually gone. I mean… the fashion (the hats! the dresses!), the food… and of course I love a good mint julep! And you know how much I love the South. I also trust + love the VV girls, so I knew we would be in great hands.

The weekend was incredible. It was a fantastic group (a mix of editors + bloggers – I made some awesome new friends!), we stayed in the most gorgeous house, AND they had the most wonderful (and hilarious) photographer Demi who took all of these beautiful photos for us which took a lot of pressure off of us. Her photos were so good that what I’d originally intended to be one blog post has turned into two (sorry to stretch things out but not actually sorry because she captured the trip so perfectly!!) The trip itself was the perfect mix of doing cool, interesting stuff (touring Woodford Reserve was so amazing!), but also getting eight hours of sleep. Yes, I’m old. I embrace it. As for Derby itself, well that was a true bucket list day, but we will have to get to that next week… I cannot wait to share the photos from that – they’re insanely gorgeous.

This was our house. Out of a dream, right? It looks a lot like the house in Sweet Alabama.

With Jess, Madeleine (from Country Living), and Anna above. I had known Anna for ages through blogging and fashion weeks of years past, and I had been reading Jess’s blog forever but it was my first time meeting her in person. We had so, so much fun.

Vineyard Vines dressed us for the weekend and I LOVED this off the shoulder dress (it’s also available here). It’s so comfortable (runs true to size) and I love the blue + white take on the banana leaf pattern. I paired it with my Marion Parke sandals which are the most comfortable. If you have a vacation coming up (or just want a new easy dress) I can’t recommend this one enough. I wore it through a day of brunch, bourbon touring/drinking, and dinner and it was perfect for each of those things. I also kept my jewelry on point… it’s hard to tell but my charm bracelet has all of the ingredients for a mint julep!

Clearly instagramming something very important…

Our first stop of Friday morning was brunch at a cute spot called The Porch. I tried to keep things healthy, going for green juice and an egg scramble but THOSE DONUTS. With chocolate sauce. Pure magic. How could I say no to them? When in Kentucky…

After brunch, we headed over to Woodford Reserve for a private tour + tasting. We learned a lot about bourbon, but what I found most interesting was that back in the days of Prohibition, people could buy medicinal bourbon (kinda like medicinal marijuana today). So a lot of people were “sick” with doctor notes.

Woodford is the oldest, slowest bourbon distillery. The aging process takes 5-7 years!

The key takeaway for me from the whiskey tasting is that I am SUCH a wimp. I love a mint julep or a whiskey lemonade but I was the embarrassing person coughing the whole time. Bourbon packs some HEAT and I definitely need a mixer. I had to ask for water. Our guide suggested trying the Double Oaked Bourbon over vanilla ice cream which sounds more my speed.

After dinner we headed to The Speed Art Museum, where the tourism board had taken over the entire museum for a private dinner. It was really cool. I was impressed by the museum – they had a beautiful exhibit highlighting the female impressionists, and their permanent collection had pieces from several famous/prominent artists.

After dinner, we headed to a cute bar downtown called The Silver Dollar. I was home and in bed before midnight… had to rest up for the main event the next day!

photography by Demi Ward.


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Leave a Comment


  1. Oh my goodness, the photos are stunning! I’m glad to hear that the press trip was great. It’s evident from your smile! 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    5.11.18 Reply
  2. Woodford is my husband’s favorite, im Excited to impress him with my knowledge of what their factory looks like! Haha. That house in unreal, these photos seriously make me want to get in my car and drive to Kentucky. What a truly wonderful weekend!

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    • Haha love it!!! It was wonderful – you (and your husband!) should definitely get to Louisville at some point (preferably for the Derby + a Woodford visit) if you can!

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  3. Looks like such a fun experience and the photos are amazing! Can’t wait to hear about the rest of the trip!

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  4. Taylor:

    One of my best friends from college is from Louisville and I love any chance to go down and visit her. Louisville is such a great town with southern charm. I’m so glad you had a great time!

    I love Jess’ blog, she’s one of my favorite Chicago bloggers, and I was so happy to see you guys on this trip together!

    Love that you had a relaxing, but fun travel weekend! Can’t wait to see the post on Derby day!

    xo, Taylor

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    • Aw I love that! Jess is awesome!! It was our first time meeting in person and we had the best time! xx

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  5. Woodford Reserve is the first bourbon I ever tasted–it’s my Dad’s favorite and he always has a bottle! Your trip looks like it was wonderful and I can’t wait to read all about the Derby!

    Sarah | all in the details

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  6. My gosh! Everything looks so amazing! I loved your white and blue dress!
    MarĂ­a Eugenia |

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  7. Adorbs! I saw Anna earlier this week, and she was sharing some of the hilarious stories from the trip. It sounded SO fun! Happy Friday!

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  8. Chrissy:

    This is a dream and I cannot wait for part two! Vineyard Vines, Woodford, Derby all wrapped into one.

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  9. Denise Atwood:

    Great photos and a fun commentary of your trip! thank you for sharing!

    5.12.18 Reply