A “Bucket List” item for a lot of people is The Kentucky Derby annual horse race at Churchville Downs in Louisville, Kentucky. It is always held on the first Saturday in May, and “The Oaks” is the day before. It has been on my bucket list for a while, and our 2015 trip exceeded my expectations! I would describe the atmosphere as an adult Disney Land. Everyone is happy, happy, happy! The locals are very hospitable, and all in attendance feel lucky to be there. The cocktails are flowing, the horses are racing, and the well-dressed crowd is enthused.

 

Must See Places

While in Louisville, there are a few places that are a must-see. The famous Seelbach (Hilton) Hotel is where Daisy – of Great Gatsby fame – wed Tom. They shot part of The Great Gatsby movie there. Seelbach Hotel

The other must-see historical hotel is the Brown Hotel, on Fourth and Broadway. They have recently had a $12 million renovation. Brown Hotel

You can get a tour of how bourbon is made, which Kentucky is known for. Go to Bourbon Tours a list of places to go.

 

Restaurants

An interesting place to eat is Proof on Main, at 702 West Main Street. The food is good, but the real appeal is that they have a fascinating modern art gallery. You can dine at this casual restaurant, have a drink at the bar, or just check out the art gallery. We went there to debrief on Sunday about the fun we had at the races, and we were drawn to all of the interesting artwork. Proof on Main

Jeff Ruby’s Steakhouse is a favorite. It is hard to get into, so call way in advance to make a reservation. Jeff Ruby’s Steakhouse

 

What to Wear

My husband Daniel and I had a lot of fun picking out our outfits and accessories for The Oaks and The Derby. The Oaks has a tradition that all in attendance wear pink to honor cancer awareness. Daniel chose a pink Ralph blazer with sear suckered pants, and brown and white buck shoes. On Derby day, he had a crazy multi-colored jacket that he borrowed, with white linen pants. Each day he had a horse race themed bowtie and belt, which we purchased at Vineyard Vines. (They have a whole line of Derby clothing and accessories. Vineyard Vines )

 

Hats

I found a pink hat from a local person in Dallas, and then borrowed my Derby day hat. All the local department stores in Dallas sell hats that time of year. The one I borrowed was from my friend Allison who bought in on-line. If you do not have a hat picked out by the time you arrive, do not fear! There are plenty of shops that carry hats in Louisville.

 

Dresses

I picked out my hats, then I shopped for my outfits. Coincidentally I was going on a girl’s shopping trip to NYC the week before The Derby, so I decided to shop there. I found my pink dress at a local boutique in SoHo, and my Derby day dress at Century 21 – which is like a Marshall’s of TJ Max on steroids. Whatever you choose, make sure you will feel comfortable in it all day. You will probably get dressed by 9:00 am, and people stay in the outfits and hats after The Derby, and go to dinner as late as 9:00 pm.. This is probably because it would be a pain to fix your hair, so why not just stay in your hat and dress?

 

Outerwear

The weather for us was in the 50s for the low, and in the 70s for the high, so I brought outer-wear for the morning. Plan on choosing outer-wear (for cold or some years for rain) ahead of time, so it coordinates well with your outfits. I grabbed something from my closet to pack at the last minute, and I had to keep on taking it off for pictures.

 

Accessories

I obsessed over my shoes and handbags more than anything because of Churchill Downs’ security.

 

Shoes

There is a lot of walking since you cannot get too close to the track on Derby day, therefore most ladies wear flat shoes or flip-flops, and then carry their high heeled shoes. When I got there, I discovered that the smartest ladies had fashionable designer flat sandals that went well with their outfits. After carrying my shoes all day, and switching off from flats to heels and back throughout the day, I decided this is the way to go. I wore some chunky heeled black shoes with bows down the front for The Oaks, and found some sheer black heels to match my Derby dress. I then wore silver ballet flats for the serious walking.

 

Handbags

As for my handbag, the official website says that you cannot carry a bag larger that 12×12. Being the rule follower that I am, I was in Nordstrom and Neiman Marcus measuring every handbag that I considered. (Yes, I am that anal.) I ended up with a small Kate Spade pink handbag for The Oaks, and a black Tory Burch handbag for The Derby. Both are crazy small, but I had room for my phone in my plaid shoe bag. As it turns out, I saw a lot of people with larger handbags, but no one told them not to bring them in. I always say safe than sorry, but I do not think they will confiscate your bag if it is 14×14 instead of 12×12!

 

Jewelry

I am obsessed with Lauren Kate Design jewelry. Lauren Kate Design Every precious stone is one of a kind, and are dipped in 14 carat gold. The owner, Stacy Mullikin chooses high quality, beautiful chains. Lucky for me she lives in Dallas! I took my outfits over to her and she helped me pick the perfect jewelry.

 

Organization

I am such a light packer, but this trip was an exception! I typically bring one pair of shoes, and one set of jewelry that can go with everything, but I could not resist packing for each day. I wish I had shipped my hats to and from the hotel, to save the pain of bringing them on the plane. Also, for some reason, American Airlines from Dallas Fort Worth International Airport decided to give us a tiny plane to Louisville. This made carrying luggage on difficult. If you have valuables (such as jewelry or your Derby tickets), valet your luggage at the gate, or take them out all together and carry a small bag on. When I travel, I am fearful of lost luggage, so I at least carry my makeup, toiletries, and at least the first day’s outfit on the plane with me. If you valet your luggage – especially if you do not have a lay-over – you should not have an issue will it getting lost.

 

Transportation

Uber to the rescue again! We found a great Uber driver who we were able to work with the whole time. He quickly found the best spots to meet us. Ask your driver to drive through the neighborhood near the track. The first day on the way there, our driver went down the main street that the track is located, and we finally hopped out after stand-still traffic, and walked several blocks to the front gate. For the way back to the hotel, our driver figured out that if we walked down just a few short blocks through the neighborhood and meet him at the shopping center, he could get us out faster.

We stayed near the Seelbach and Brown hotels, and there are a lot of shops and restaurants within walking distance.

 

Tipping

We gave our Uber driver cash on top of the Uber tip that is included in the ride.

You also will want to tip the hard-working people serving you food and drinks. I think $1.00 every time or every other time if you go to the same person is sufficient.

Tip the washroom attendants. They keep the restrooms amazingly clean, and will hand you a towel. I would tip around .50 cents per visit.

Restaurant tips are 15-20%. I would tip on the high end, because they are crazy-busy Derby week!

 

Practical Tips

• Ship your hats to and from your hotel
• Find a driver the first day, and get his phone number
• Consider wearing cute sandals
• Go to the horse track gift shop on the Friday of The Oaks, or early on Derby day
• We attended a wedding the week after the 2014 Derby, so we went to the stadium to check everything out for our 2015 Derby trip. It was blazing hot, so we knew we would want covered seating. We had perfect weather, (apparently the best in 40 years), but it has been known to rain, so another reason to want covered seating.
• Wear sunscreen even if the high is supposed to be 70 degrees, and you have covered seating. (Like in our case!) You will want to walk around, and you will get sun exposure.
• Go to The Infield, and walk around no matter where you are sitting. It is across a tunnel from the ticketed seats. You see a lot of characters and “costumes.”
• Make your bets all at once at the beginning of the day. We kept on standing in line after every race. Derby Day lines can get long. Races are about every 30 minutes, and an hour and a half before the big Derby race.
• Check out the horses in the Paddock. It is interesting to see them up close, and all of their muscles and real beauty.
• Bring a lot of cash for alcohol. It is expensive!
• If you would like to bring home all of the glass beverage containers that you get your drinks in, ask your hotel for a box to bring on the plane, or ship them home. The Mint Julips, Stella beer, and other speciality drinks have a special commerative glass.
• You can call local restaurants two weeks before Derby day and order a boxed lunch. They know how to package them in clear wrappers so you are allowed to bring them in. Bring bottled water too. They are expensive and they ran out at the end of the day at the stadium.