I’ve always wanted to go to the Kentucky Derby, but have never been able to talk anyone into going with me. Either they’ve been once, and that was enough, or they weren’t interested due to the exorbitant price of a seat.
Finally, I decided to go on my own through my vacation club Dreamtrips, who offered a package that included three nights at a hotel in Lexington (not Louisville), transportation, a reserved seat in the Grandstand for the Derby, a horse farm tour, and a bourbon tasting for only $1,860 after I applied 630 points.
Given a package from the Kentucky Derby for the same seating with the addition of a concert, food and beverage cost $1,799 not including lodging which was $1,600, I thought I got a pretty sweet deal.
Lexington, Kentucky
I arrived in Lexington on Thursday evening. The hotel, Hyatt Regency Lexington, offers a free shuttle, but due to landing at the airport during rush hour, I was going to have to wait 20 minutes just for the ride. Anxious to check in and get situated before our welcome reception, I opted for the $15 Lyft ride.
The Hyatt Regency Lexington
The Hyatt Regency Lexington was hopping as it is located near the University of Kentucky which was holding graduation ceremonies over the weekend. The hotel includes a restaurant, bar, indoor pool, tiny gym and decent rooms without much insulation. There was really nothing exciting about the accommodations except that the Hyatt seems to be making a concerted effort to go green where possible. My room included a recycle trash can and the elliptical machines created energy when used.
Maker’s Mark Bourbon Tasting
Our welcome reception included a Maker’s Mark bourbon tasting. I had actually been on the tour of the Maker’s Mark distillery 8.5 years previous where I got to dip a bottle in the signature red wax. Thus the tasting in the hotel bar wasn’t too exciting comparatively, but it was fun to meet everyone in the group.
Our tour leader handed out our coveted Kentucky Derby tickets and informed us we were upgraded from sections 226-228 to section 221. From what I learned, sections 226-228 were recently added to Churchill Downs. They include bucket seats, some of which are covered, as well as food and drinks. They are located behind the start line in the Grandstand area. In comparison, Section 221 is in the much better Courtyard location, between the start line and the finish line, however, the seating is bleacher style and the concessions are not included.
Horse Farms and Distilleries
Anyway, we stored our tickets in a safe location on Friday while we spent the day at the Kentucky Horse Park, Hayden’s Stockyard Eatery, and Alltech Lexington Brewing and Distilling Co (aka Town Branch Distillery). Before our 9am start time, I walked down to the 24-hour diner called Tolly-Ho for some fried eggs and bacon which were delicious.
The Kentucky Horse Park
Next, I joined our group in two sprinter vans for our trip in the rain to the Kentucky Horse Park. It was a little weird for me to go on a tour at a facility at which I used to compete in Hunter/Jumpers every summer! Uniquely, despite having spent weeks at the facility, I never bothered to go visit the museum, the retired Derby winners, or Man O’ War’s grave. Like most teenagers at the time, I was only into what I was doing!
We arrived by 9:45, hopped on the 10am horse-drawn trolley for a short tour of the nearby facilities, and then joined the Hall of Champions Show at 10:30am. At the show, stable hands lead retired racehorses into a pavilion as an announcer proclaims its successes. We saw Funny Cide and Go For Gin, which I got to feed a peppermint.
At 11am, we ventured to see the Parade of Breeds where riders show off different types of horses in a performance. Normally, the riders don costumes, but on this rainy day they did not.
The dreary weather kept us from visiting the draft horse barn as we returned to the museum near the facility entrance. The museum included countless trophies, variety of memorabilia from famous racehorses, and even a horse statue that looks like the Broncos mascot, Thunder.
With a break in the rain, I took a quick jaunt to see the Man O’ War statue under which the amazing racehorse is buried. Along the way, an exhibit shows the length of a racehorse’s stride at a full gallop, 24-28 feet for the best!
The poles behind the start represent 24-26-28 feet represented by John Henry, Secretariat, and Man O War respectively
Hayden’s Stockyard Eatery
After a few hours at the Kentucky Horse Park, we went for lunch nearby at Hayden’s Stockyard Eatery. It is located in a facility that includes a gift shop and an auctioning room for livestock. Hayden’s Stockyard Eatery had about one healthy item on the menu and the rest was fried chicken, burgers, and giant pieces of cake. For southern cooking, it’s a good place to stop.
Alltech Lexington Brewing and Distilling Co (aka Town Branch)
A visit to Lexington would not be complete without a tour of a bourbon facility on the Kentucky Bourbon Trail Map. As such, we visited the Alltech Lexington Brewing and Distilling Co which is conveniently located in downtown Lexington. While the convenience is nice, the ambience of a hillside distillery tour, like Maker’s Mark, is missing. By the same token, the distillery is unique as it also brews beer. Their sales exploded when Oprah tasted its Kentucky Bourbon Barrel Ale and said, “WOW”.
The Irish entrepreneur, Pearse Lyons, founded Alltech Lexington Brewing and Distilling Company in 1999. It is part of a family of distilleries owned by Lyons including Dueling Barrels in Pikeville, Kentucky; Pearse Lyons Distillery in Dublin, Ireland and Foxes Rock in Newry, Northern Ireland.
Our tour of Lexington Brewing and Distilling Company began on the beer side. The tour guide, who seemed a little new to the job, stumbled through his brief presentation of beer making as we toured the brewery and then went into the tasting room. We were given four tokens to use for tastings. We could use all four on beer or save them all for bourbon or try any combination thereof.
I used two tokens for beer and two tokens for bourbon at the next tasting room after we toured the distillery. I’m not an alcohol connoisseur of any type, but the Town Branch Bourbon which is new relative to Kentucky standards and the beer seemed good. I will claim that the complimentary dessert drink which featured their Bluegrass Sundown tasted like coffee ice cream, and it was excellent!
Brewery 
Beers 
Distillery 
Tasting Room 
Tasting Room 
AMAZING! 
Town Branch Distillery
Shakespeare and Company
Our day of tours finished in the late afternoon with enough time for me to freshen up for a night out with a high school classmate at Shakespeare and Company. The restaurant, along with several others, was just a few blocks away from my hotel. We really enjoyed catching up, and I gained a lot of insight on the racehorse world from Michelle, who used to be a television reporter. I think I may have to return to Lexington to see the horse sales at Keeneland and to visit Old Friends, a racehorse retirement facility.
The 145th Kentucky Derby
As I mentioned above, my reason for coming to Lexington (a much cheaper alternative to Louisville) was to see the Kentucky Derby in Louisville. The day had arrived! I awoke early to primp. Dressed in my flowery pink dress, black hat with a wide brim, sandals, and pearls I joined our group who had split in two in the lobby.
The first bus left for Churchill Downs (1.5 hours away) at 7:30am allowing for a breakfast stop at Cracker Barrel before arriving at the 145th Kentucky Derby around 11am an hour after the gates opened. The second bus, which I joined, left at 8am allowing for a breakfast stop at Cracker Barrel and a bourbon tasting at Buffalo Trace before arriving at Churchill Downs around 1pm.
I was torn about which bus to take. Scott, the tour leader suggested the Kentucky Derby would be dreary, no pun intended, in the rain which was forecasted to begin at 11am, especially if our seats were not well covered. Being a fairweather fan, the thought of being wet and cold, spurred me to choose the later van even though I didn’t really care about tasting anymore bourbon since I’m not much of a drinker.
Breakfast at the Cracker Barrel
Our van of seven left only shortly after the first van, and we arrived at Cracker Barrell just as they were getting their food which took much longer for them as they were in a larger group. After a good breakfast at the southern chain restaurant, we carried on to Buffalo Trace just six miles away. We made it just in time for the hour-long tour that leaves on the hour.
Bourbon Tasting at Buffalo Trace
The Buffalo Trace tour was far more in depth than that of Town Branch. The gentleman providing the tour was basically a bourbon encyclopedia. We learned of the history, the storage and taxing, the process and more. We walked outside to the aging warehouses and tried to see the distillery area, but it was locked.
If this were my first distillery tour, I likely would have called it excellent, but now that it was my third, my attention was fading, in particular because I didn’t want to be caught outside with rainstorms on the way. I wanted to get to the Kentucky Derby in a dry dress if possible! While usually I enjoy the tour more than the tasting, today I was relieved to finally enter the tasting room.
We tried five products starting with the White Dog, YUCK! This was like drinking liquid fire. My tongue, cheeks and lips burned. I wondered if they gave us this shot first to make their bourbon taste as smooth silk. Who knows, but it did. Being the novice that I am, I had never heard of Buffalo Trace. I didn’t know that it is the world’s most award-winning distillery, and that it is the oldest continuously operating distillery in the United States. Continuously being the key word as it remained open during Prohibition by finding a loophole in the law. It’s bourbons as well as its dessert drink were excellent.
Parking at the Kentucky Derby
Finally, we headed to the 145th Kentucky Derby. While there is paid parking at the Derby and offsite at specific locations, owners of homes in neighborhoods nearby Churchill Downs charge for parking on their lawns. We parked in a neighborhood near Wizard and Oleanda and got in and out rather easily. It was only a short walk from the Clubhouse Gate.
After passing through the metal detectors, buying a program and a $15 mint julep (which were everywhere), and stopping at the row of Porta Potties, we weaved through the crowds while hardly glancing at the surrounding vendors as we dashed to find our seats. We wanted at least one picture of us in a dry dress without a poncho.
Section 221
Not familiar with the facility, we had a difficult time finding section 221 from the Clubhouse side. We had to walk around the paddock and tunnel to the infield to reach the Courtyard section. With a little help from security, we found our way. We had the last row of the covered section with a very low roof. We were definitely protected from the rain, but also the view.
view from standing on the back row of the bleachers 
We arrived between the 6th and 7th race of the day, so we took advantage of the empty track and snapped a few photos of us in our fancy attire at the front of Tier 2. A light drizzle started soon thereafter.
We felt fortunate to be in the covered area until all the folks in their rain-soaked ponchos seeked cover. They lined up against the back wall behind us. It didn’t take long for the inebriated to knock off our hats as they walked by or to simply douse us with rainwater dripping from their plastic raingear sleeves. With tasting five bourbons before lunch, I thought I got a head start on the Kentucky Derby drunkfest, NOT! At least it was fun to look at the hats!
fun hat in our section 
more fun hats in our section
For the next four hours, I only left my seat once to use the restroom and to get some food. The limited concession stands with long lines prompted me to get kettle corn at a free-standing cart which also had cold pretzels. At least I got food before they ran out, which some of our group experienced!
Twin Spires Betting App
Fortunately, I downloaded the Twin Spire App in order to bet. This saved me from entering any betting lines, and from throwing any paper tickets on the ground that ultimately could have been winners after the controversial finish! I spent much of the idle time studying the program but failed at placing winning bets. I left $40 in the hole. Not bad since I brought $100 to waste. But it’s more fun to win!
start gate for a grass race 
a grass race earlier in the day
I would have liked to view the horses in the paddock before I bet, but the rain and the crowds deterred. It was an effort to see any of the horses in person. At least I got to see the roses nearby and the iconic twin spires.
the paddock 
the roses 
the twin spires
The Race
Soon the race we had all been waiting for approached. In anticipation, we all stood on the bleacher seats. After the singing of the Star-Spangled Banner and My Kentucky Home, the companion ponies led the Kentucky Derby entries to the start gate. Once they were loaded in the starting block, the gates swung open, and the horses raced across a muddy track beneath a steady rain.
the derby horses with companion ponies 
the derby horses with companion ponies 
my view of the Derby
Maximum Security was ahead the whole way and crossed the finish line first. I almost picked Maximum Security to win, but instead put him in a boxed exacta with Tacitus who came in 4th (and then 3rd) after the disqualification. I think I would have really been disappointed if the DQ resulted in me losing a winning bet!
The Outcome
I feel for Maximum Security, its jockey Saez, and owner West. Imagine winning the Run for the Roses, the greatest two minutes in sports, only to find out 22 minutes later that the horse was disqualified for veering out of his lane after Country House, the second horse, objected. Sadly, the second horse was not obstructed and had no chance to catch Maximum Security.
Having said that, Maximum Security did impede War of Will with the lane step out, but interestingly it can be argued that War of Will knocked into Maximum Security’s hind end multiple times before he leapt to the side. It appeared that Saez attempted to control his mount, but to no avail.
I’m not here to pick a side. I can see both the arguments for and against Maximum Security, but frankly could hardly see the track, so I have no say. I caught a glimpse of the horses twice for a total of about three seconds and otherwise watched the big screen. After the objection, my phone was blowing up with texts from friends asking what was happening. I responded, “those at home know more than us!”
It’s crushing to see a horse who has never lost a race be disqualified especially when it is the first time ever that the Kentucky Derby has DQ’d the winner. In addition, the subsequent winner was the 2nd biggest longshot in the Kentucky Derby history. Country House wasn’t about to win on its own. Regardless, it will be a controversy long talked about, especially with all the betting losses, and a historic day at the United States oldest sporting event!
Tips for Visiting the Kentucky Derby
As for me, I’m glad I went to the Kentucky Derby. Having said that, I could have improved my experience in many ways. This is what I learned:
- Parking in the neighborhood was easy.
- With rain starting a few hours after the forecast, I would have liked to arrive an hour or two earlier to walk around. Many in my group didn’t agree, but I would have liked more time to explore.
- I would skip buying the two page race sheet on the street, save $4, and only buy the official program for $5 inside. I mistakenly bought both.
- I would wear a simple dress and spend a lot of time on my hat to make it fun!
- The Kentucky Derby is more of a party than a horse race. The media only shows the glamorous parts.
- Tier 1 and Tier 2 don’t require fancy clothing. A simple sundress with a fun hat will suffice.
- Tier 3, in particular section 312, seems like the best value for the money. It’s covered with a good view of the track and the stands. Unfortunately, I believe it requires a purchase of an entire six-seat box and sells out quickly.
- On a sunny day, row A of tier 1 in the clubhouse would be awesome for a place against the rail near the finish line, but it rains 50% of the time and is otherwise hot, so it’s a bit of risk for the money.
- Attending the Oaks when the fillies race the day before and then going to Keeneland in Lexington on Derby Day for live music, betting and racing might be the best option!
Though these articles are slightly dated, I found them helpful resources for attending the Kentucky Derby:
A Guide To Buying Tickets To The Kentucky Derby
Parking Tips for the Kentucky Derby
Overall, I vote for a Kentucky Derby redo! ETB
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Fun! I feel like the people watching would be awesome. Would love to see all of the different hats.