Kentucky Bourbon Sampler Weekend Itinerary

Kentucky is well established as the whiskey capital of the United States. The majority of the distilleries are located between Lexington and Louisville, although they can be found all around the state. If you enjoy whiskey and bourbon, a tour of the Kentucky backcountry is a great weekend trip. A couple of days filled with whiskey tastings and tours is the right amount for a trip. Any fewer and the journey often isn’t worth it. Any more days and visitors start to grow tired of the whiskeys at the end of the trip. And for those not as enthusiastic about whiskey, fear not as there are other things to do during a weekend in Kentucky (however whiskey will make up the majority of this trip). The following is a great outline for how to spend a weekend in Kentucky as a Bourbon Sampler.

Day 0

Flying In

This weekend’s itinerary consists of a full Friday, a full Saturday, and a full Sunday which is the perfect amount of time to spend touring parts of Kentucky. That does mean many people will need to take off Friday in order to make this itinerary work. Therefore, I recommend getting to Kentucky the night before starting this itinerary, hence the Day 0 flight. Due to its central location, Kentucky isn’t a very far flight from a large percentage of the US population. For example, flights from Washington, D.C. are about 2 hours, flights from Atlanta are about 1 hour and 20 minutes, and flights from Dallas are about 2 hours and 10 minutes. All of these are pretty easy flights that could be done the evening prior to starting the whiskey sampling. Obviously, if you live within close driving distance, driving is another option.

As mentioned previously, a large number of the major whiskey distilleries are located between Louisville and Lexington. Visitors have a choice of flying into and staying in either city. The vast majority of the time, it is recommended to fly into and stay in Louisville. Louisville is larger than Lexington and therefore has more flight options. This generally means cheaper options and better times to help you not take time off work on Thursday. Since Louisville is larger, this also means more hotel options, more dining options, and a little more to do in the city if you like nightlife. The remainder of this itinerary will assume that visitors are using Louisville as their home base.

Pick Up Rental Car

The majority of the distilleries are located in rural Kentucky. While there is some public transportation in Louisville, there is none that will get you to most of the whiskey distilleries. Therefore, it is almost an absolute necessity to have a rental car. The only possible exception to this rule is if you are going to pay for a private bus tour of several of the distilleries. Private bus tours are expensive, but they do transfer the responsibility of driving to someone else. This is an important consideration when doing a whiskey tour like this. Do not under any circumstance drive under the influence. Visitors will need to limit consumption to an amount where they are within the legal limit deemed safe for driving.

Alternatively, you will need to have a designated driver. If you don’t have someone who can drive or you don’t want to ask someone to moderate intake, please look into the private tour options to ensure that your visit in Kentucky is safe. Personally, I go on these tours to sample different bourbons/whiskeys and to learn the differences in production processes between different distilleries. I limit the samples to three or four (which is similar to the volume of one drink). With these tours/tastings taking one hour and with spending a little additional time at each distillery, I have always been good to drive. However, I understand that many will want to indulge so be your own judge on the value a private tour provides to your style of trip.

Assuming that you have decided a rental car is appropriate, you can pick one up at the Louisville airport. The airport has all the major rental car companies including Alamo, Avis, Budget, Dollar, Enterprise, Hertz, National, Payless, and Thrifty. The rental car counters are all around the baggage claim at the airport, and the rental cars are conveniently located in the attached parking garage. It’s always nice when a shuttle bus isn’t required to get to the rental cars at an airport.

Drive to Louisville

The Louisville International Airport (airport code SDF) is located just on the outskirts of Louisville. The vast majority of people will want to stay in the downtown area of Louisville. This is a simple 10-minute drive away from the airport for most locations. Once in downtown, check into your hotel or accommodations.

The rest of the evening’s plans will be up to you. I often arrive late since I fly after work. I typically eat in the airport or bring food onto the plane. Therefore, I rarely do anything that first night. However, if you get in a little earlier in the evening, it may be nice to explore the area surrounding your accommodations. This way you get the lay of the land and understand the restaurant and entertainment options around you.

Day 1

For the first full day of the Kentucky Bourbon Sampler, visitors should start their tour of the Kentucky distilleries. Many of the tours and tastings require reservations. Therefore, if you plan early, you will be able to craft the itinerary you want. However, it is not uncommon to piece together an itinerary around distillery availability if you start planning a little later.

Each full day of your Kentucky Bourbon Sampler Itinerary should be able to comfortably accommodate three distillery tours and/or tastings. While proper planning and really tight turnaround times could make seeing four distilleries in a day feasible, I don’t recommend it. Part of the enjoyment of this itinerary is to relax and enjoy time with your travel companions while sampling some whiskeys and bourbons.

Finally, the whiskey distilleries you visit each day should be heavily dependent on your personal preferences. This itinerary will include some of the major labels and most popular stops that combine to make a nice itinerary. However, visitors should always customize the stops if they have particular favorites or dislikes. With all that being said, let’s get into the itinerary for the day.

Wild Turkey

The first batch of nationally known distilleries on this tour are located around or near Lawrenceburg, Kentucky. While they are so closely located that they can be visited in almost any order, the opening/tour times of Wild Turkey tend to make it a favorite for being first on the list. I recommend a tasting only at this stop. Many tastings will offer some products that are rare or unavailable to the public normally. While Wild Turkey doesn’t have any exclusive products, they do offer tastings of some of their less common labels.

The other reason to choose a tasting only is that tours start to be repetitive after you have seen several. There are some that offer different sights, but many are the same. While this is only the first stop, there are several stops that are better for tours later. Therefore, save your money and time to enjoy more whiskeys.

Four Roses

The next stop on this itinerary is Four Roses which is just a short drive from Wild Turkey. While the bourbon is definitely good at Four Roses, this might be a stop that you visit for the tour more than the tasting. The distillery consists of several buildings built in Spanish Mission-style architecture. The site is even listed on the US National Register of Historic Places. Because of this, Four Roses is a great place to do a combination tasting and tour. This will allow you to see the interior of many of these historic buildings. Throughout the tour, visitors will be amazed by the traditional equipment that still goes into making bourbons. While there have definitely been updates, visitors should be able to envision much of the equipment being used a hundred years ago.

One thing to be aware of with all distilleries is that they can have seasonal schedules for production. This means that depending on the time of year you visit guests could witness ongoing production or a shutdown. While you can still see the equipment and appreciate how the process works during a shutdown, it might not be quite as exciting since you won’t see the actual products moving through the stages. However, on the upside, the production of whiskey can be fairly loud (especially where grain is being milled). Visiting during a shutdown will be a little easier to hear and talk to your guide. Be sure to check each distillery’s website when you book your visit to determine what will be available.

Lunch

After two distillery visits, it will likely be 1 PM or later. Most people will be getting hungry. This is a great time to stop in downtown Lawrenceburg for something to eat. There are a number of food options in this small town.

One of the most popular is Heavens to Betsy! Bakery and Deli. This small restaurant is a local favorite despite its “hole-in-the-wall” location. The restaurant doesn’t have a website beyond the Facebook page they maintain. The restaurant has tasty, simple, and cheap food that is sure to cure any whiskey-fueled hunger. In addition to the traditional menu of hot and cold sandwiches, soups, and desserts, they also have a number of specials that are always unique and wonderful creations. For example, where else can you find a ham, bacon, and swiss sandwich with jalapenos and blackberry jam? Another favorite is the hot ham and swiss sandwich with artichoke spread and red pepper jelly.

Woodford Reserve

The final stop of the day is at Woodford Reserve. Woodford often markets itself as a more upscale bourbon brand. This marketing will show around the distillery and property. While the process of making whiskey won’t differ much from Woodford to the other distilleries guests will have seen, the building architecture and rolling landscape are an experience to explore. This makes a tour more interesting than it would normally be. If a tour isn’t available, much of the exterior of the buildings can be self-toured so go ahead and book a tasting. Arrive early or stay late and explore the grounds of this distillery on your own.

Whiskey distilling began on the Woodford Reserve site in 1812. Similar to Four Roses, the main distillery building is listed on the National Register of Historic Places. Unlike Four Roses, the Woodford Reserve distillery is also a National Historic Landmark. Whiskey has been produced on and off at this distillery since its inception. The distillery has also changed ownership many times throughout its history. The current brand was introduced to the US market in 1996. Therefore, while the distillery is quite old, the Woodford Reserve bourbon produced today is a fairly recent development.

Return to Louisville

By this point, most visitors will be ready to return to Louisville to rest and freshen up for the night’s activities. Louisville is about an hour’s drive from Woodford Reserve so it will take a little bit to get back. Given the full day, I generally prefer to take some time to relax at my accommodations, refresh with a shower, and get dressed for the evening. This generally means a later start to dinner which isn’t an issue in Kentucky as most distilleries don’t open until 9 or 10 AM. Again, this is designed to be a relaxing and leisurely trip (so be sure to keep it that way).

Day 2

With the first day of the Kentucky Bourbon Sampler Itinerary in the books, it’s time to set off on another day. Similar to yesterday, the second day will explore three distilleries. Two of the distilleries on the itinerary are national names. The final distillery is a little off the beaten trail, but it is a great experience due to the grounds and the variety of the experience.

Bulleit Distilling Co.

The first stop of day two is Bulleit Distilling Company. Bulleit markets itself as a frontier whiskey. Despite that name, Bulleit is going to be one of the most modern distilleries on the itinerary. The visitor center and tasting room are very new and built with a very industrial aesthetic. The actual distillery buildings are also fairly new looking and filled with modern technology. Guests who take the tour will see a modern control room that could very well have come from a refinery or paper plant. Unfortunately, the overall tour experience is somewhat lackluster. Visitors get to see a large number of fermenting tasks, but otherwise, the tour wraps up with staged displays of the column still and barrels. The enduring memories of this tour for me are just the modern technology in use.

Continuing with the theme, the tasting at Bulleit has modern elements as well. Each tasting is accompanied by paired lighting, sounds, and scents. This is unique in that no other distillery is doing a similar presentation as far as I am aware. While there is probably some science behind the pairings that influence the experience and tasting, I think it had a minor impact. Despite some of the downsides, I still recommend seeing Bulleit as it is so different than everything else on the Kentucky Bourbon Trail.

Buffalo Trace

The next distillery to visit is Buffalo Trace. Located in Frankfort, Kentucky, Buffalo Trace has made a big name for itself in the whiskey world. They are the producers of whiskey under the Buffalo Trace name as well as a multitude of other labels. Some of these other labels include Col. E. H. Taylor, Eagle Rare, Blanton’s, Old Rip Van Winkle, and Pappy Van Winkle. Many of the distilleries visited previously were mass-appeal brands without a top-shelf offering. Buffalo Trace changes this by having several top-shelf offerings in its lineup.

Some of the top-shelf offers make it into a tasting every now and then, but it isn’t a guarantee. The Buffalo Trace distillery is also a very distinctive property. It’s large and industrial given the amount of whiskey that is produced on-site. However, at the same time, the buildings hold onto the old, storied ambiance that bourbon is often associated with. A tour and tasting are the correct options when coming to Buffalo Trace. A benefit of going on a tour and tasting is that those visitors have the option to purchase rarer bottles of whiskey than what is available in their gift shop.

Given the name brand that Buffalo Trace is and the desire to tour the property, reservations for tours and tastings can be hard to come by. The distillery opens reservations in batches a month at a time. When this happens, it’s not uncommon to see the tours for the whole month be reserved in a matter of minutes. Because of this, you will want to plan early for this reservation. If you can get a reservation, you will also likely have to move around other visits on your agenda to fit this one in.

Lunch

While you are in Frankfort, take the opportunity to grab lunch. Frankfort is the capital of Kentucky so there are plenty of options in the surrounding area for food. If you aren’t yet ready to leave Buffalo Trace, the property does have its own sandwich shop. The Firehouse Sandwich Stop, as it’s known, is a very small place with only a half dozen tables outside. The menu consists of burgers and sandwiches only so the selection is limited. However, it’s hard to beat the convenience of this location.

Castle & Key

The final distillery stop is Castle & Key. While the distillery occupies an old building that once housed the Old Taylor Distillery, it is one of the newest distilleries in Kentucky. The founders of Castle and Key bought the Old Taylor Distillery in 2014 and began a huge renovation project. They have done a great job as the grounds and buildings are one of the best parts of this distillery. As the name would suggest, the distillery structure was designed and built to resemble a medieval castle. The other buildings on the property don’t follow the same period style, but they have complementary architecture. In addition, there are vast grounds with walking trails and gardens that guests can enjoy during their visit.

There are a couple of different options for enjoying Castle & Key Distillery. The first is to do the traditional tour and tasting. However, at this point, many will have done five of these already so I would recommend an alternative. Castle & Key has a bar that is open to all visitors. A great self-guided option is to get a cocktail made from one of their spirits. Visitors are then able to take this on a walk of the grounds, relax in any of the many adirondack chairs, play a game of corn hole, or enjoy the river behind the property. This can be a very enjoyable and peaceful way to end the whiskey tastings for the weekend. Since Castle & Key specializes in whiskey and gin distillation on site, they have quite a few cocktails that are both refreshing and a new experience.

Day 3

The final day will take travelers away from whiskey and bourbon. While those have been the focus of the trip up till now, too much whiskey and bourbon can be a bad thing. Therefore, before whiskey starts to leave a bad taste in your mouth, swap over to some other things that Kentucky and Louisville are known for.

Churchill Downs

Churchill Downs is the famous horse race track that is home to the Kentucky Derby. The Kentucky Derby is the first race in the Triple Crown of horse racing. Known throughout the world, the Kentucky Derby got its start in 1875. The Kentucky Derby quickly took its position as one of the preeminent raves in North America by 1902. With a capacity of over 170,000, the Kentucky Derby attracts large numbers of spectators to the race every year. In addition to horse racing and betting, the Kentucky Derby has also gained a reputation as a fashionable event. This is furthered by the upscale nature of many parts of Churchill Downs.

Visitors to Churchill Downs will want to take a tour of the facilities. As the facilities as so large, it is impossible to see them all on one tour. Churchill Downs recognizes this and has put together several different tour itineraries based on guests’ preferences. All tours include general admission to the museum. The tour options include:

• Historic Walking Tour – This is an entry-level overview tour of Churchill Downs. This covers a walk through the grandstands, a discussion of the history of the race from a tour guide, and a view of the race track from the rail.
• Backstretch Breakfast Tour – Enjoy a small breakfast and tour of Churchill Downs from the infield early in the morning. This includes seeing the horses practice on the track. This tour is only available during the summer which is race and training season.
• Barn and Backside Tour – There are up to 1,400 horses on the backside of Churchill Downs during the racing season. This tour focuses more on horse training and the facilities for the horses and less on spectator facilities or the Kentucky Derby race. This tour is available from April to November and would be a good tour for horse lovers.
• Churchill Downs After Hours Tour – This is a combination of the standard walking tour and some portions of the Superstars and Spires tour. It is conducted after 5 PM so visitors will have the facility mostly to their group. However, this also means that the museum entrance is not included in this ticket.
• Superstars and Spires – This is a tour focusing on the spectator areas of Churchill Downs. It goes through all the viewing areas (including Millionaire’s Row), the betting windows, and the upscale private dining facilities. This tour still provides the history and views of the race track with the combined entrance to more exclusive areas.
• Ultimate Churchill Downs Tour – This is the most expensive and involved tour at Churchill Downs. This tour spends four hours hitting the highlights of all the other tours. It includes highlights of the track to the backside stables to the upscale viewing areas. A small lunch is provided at the end.

These represent standard tours that are generally available throughout the year. However, with the race schedule, some of these tours may not be available on certain days. The race schedule may also allow other special tours to occur. Check the Kentucky Derby Museum website for a list of tours available when you are planning to travel.

As a starting point, I recommend the traditional Historic Walking Tour or the Superstars and Spires tour. Both of these are reasonably priced and give you a good overview of the Kentucky Derby and the Churchill Downs facility. If you have a particular love of horses, the Barn and Backside Tour or one of the few early morning horse workout viewing tours would be something you should consider as well.

Lunch

The next stop, the Louisville Slugger Museum & Factory, is located in downtown. Therefore, almost any restaurant in downtown along the 2nd/3rd Street corridor or along Interstate 65 are suitable. There are tons of options so research ahead of time and stop wherever you want. This is likely to be the last Kentucky-style meal outside of something being picked up in the airport. Therefore, if there is something you have been holding out to have, now is the time.

Louisville Slugger Museum and Factory

Another famous fixture of Louisville is the Louisville Slugger company. This company got its start in bat-making somewhere around July 1884. While the factory has moved around a few times in its history, the current factory and museum location opened in 1996. For any baseball lover, this is a can’t-miss tour and experience. Even for those who are just casual fans of baseball, it is interesting to learn how this renowned baseball brand was grown.

A visit starts with a tour of the museum. There are a number of exhibits including the history of bat making, current and historical bats for MLB players, a signature wall with the signature of every previous player to use a Louisville Slugger bat, and much more. For a price, guests can even get into the batting cages and take a few swings with a Louisville Slugger bat. It would be easy to spend an hour looking around the museum at the various exhibits. The museum tour can be done either before or after the factory tour so look through the museum on a schedule that works with the rest of the day’s plans.

The other highlight of this stop is the factory tour to see the production of current Louisville Slugger bats. Tours last about half an hour and have about five stops along the production process which shows how modern Louisville Slugger bats are made. This is a mostly mechanical/computer-operated machine process now. Visitors will be able to follow the steps that change a cylinder of wood into the shaped, coated, and branded final bat.

While the tour is very interesting, it can be difficult to hear the tour guide at times. Try to stay close to the front of each group if you want to hear the commentary by the tour guide. There are also pre-recorded video explanations at many of the stops. Those at the rear of the group are likely to miss out on some of the stories/explanations in these. The final critique of the tour is that you are likely to feel rushed. Tours move on a very strict timetable with not much spacing between the groups. Therefore, you can’t stay at one station more than a few minutes watching the process. Despite those critiques, it’s still well worth the cost of admission to see and understand the bat transformation.

Fly Home

The Bourbon Sampler Weekend Itinerary is at its end. Hopefully, you enjoyed your time in Kentucky, discovered a new favorite whiskey or bourbon, and gained an appreciation for the distillation process. The Louisville airport is very small and only a short drive from the city. Therefore, traveling back should be an easy trip. If you rented a car, make sure to leave with plenty of time to fill up the gas tank and return the car before leaving.