How to Enjoy the Kentucky Bourbon Trail at a Sipping Pace

By: Jessa Gibboney

Photo snapped by Alyssa Florentine of For  Rue Photography

Photo snapped by Alyssa Florentine of For Rue Photography

Crossing the Kentucky state line, I was instantly thirsty. This is the state which produces 95% of the world’s bourbon.

As lovers of history and bourbon, my husband Ben and I longed to visit The Kentucky Bourbon Trail®. Formed by the Kentucky Distiller's Association in 1999, this lineup of thirteen distilleries runs through the heart of the state and provides a firsthand look and taste behind the art that is crafting bourbon.

Driving from Pittsburgh To Kentucky via way of Cleveland, we explored the Lexington portion of the Trail. We choose a late weekend in March, wanting to capitalize on the ease of off-season travel.

Town Branch Distillery.jpeg

Where we stayed:

Airbnb is our preference choosing accommodations. We immediately have a local guide in way of our Airbnb host, and I love probing them for local shops and eateries. Our hosts, Seth and Renee, were local business owners, running Enoteca, a wine and tapas bar, and Wine and Market, a boutique wine and sandwich shop. Their downtown apartment was situated above the tapas bar and across the street from the market. The apartment itself was quaint, no-fuss and lent itself to a cozy stay.

Where we visited:

We approached the Trail a-la-carte. We visited Town Branch® on the Friday evening we arrived. Woodford Reserve® and Buffalo Trace™ were on our Saturday agenda. Four Roses and Wild Turkey® rounded out our visit on Sunday. Buffalo Trace™ is not officially listed as a partner of The Kentucky Bourbon Trail®, but it is one of our favorites. It was worth the visit as the production behind Buffalo Trace™ is grand in scale. Tip: pay for the hard hat tour.  

While absorbing Kentucky's signature spirit, we gathered a few more tips....

7 Tips for the Kentucky Bourbon Trail:

Don't Cram.

Call it a product of the times, call it the American mentality, call it trying to achieve social media gold, but I am guilty of cramming in as many activities as possible while on vacation. I have this limited window, maybe two days or a week, and I want to maximize it. Overpacking my days, however, leads to the oversight of a moment. I do not cherish the time and space as it deserves. I miss the guts of a memory.

Ben and I set out not to over-plan our extended weekend in Kentucky.

We had three days and were going to enjoy the distilleries we visited at an unhurried pace. That was not the case for those around us.

Throughout the trip, Ben and I witnessed folks exiting distillery tours early or rushing to group vans upon conclusion to ensure they reached their next scheduled informative outing. They were on a strict timeline to maximize the distilleries visited in one day.

Most of the distilleries have business-type hours, approximately 10:00 am until 5:00 pm. Distillery tours are approximately an hour and range from $5 to $15 per person. Some distilleries, such as Maker’s Mark® and Woodford Reserve®, offer more extensive tours or classes for a higher price.

Ben and I opted for the hour distillery tours. They were small group tours with an in-depth look at the work and tradition behind the distillery. Tastings were the finale of the tour. Two distilleries a day was our approach.

This was the ideal amount for us. It allowed time to ask questions following the tour, cheers glasses with fellow bourbon lovers and communicate our gratitude to the experts.

Buffalo Trace Barrel Room.jpeg

Kentucky straight bourbon whiskey, by law, is produced in Kentucky, must be at least 51 percent corn and aged for at least two years in a brand-new, charred white oak barrel. Two years, at the minimum, it sleeps in rows and absorbs its flavor and color. The least we could do is visit its birthplace for more than an hour.

Our favorite distillery surprised us. Woodford Reserve® is one of the smallest and oldest distilleries on the trail. Here is where its appeal begins. Whiskey has been crafted on these grounds for 206 years. The background of rolling hills enhances its charm. The bourbon is premium. The tasting room was exquisite. Our guide provided the most in-depth information about flavors and how they differ across individual palates. Ben and I left with a new favorite bourbon, Woodford Reserve® Double Oaked. This craft bourbon is matured in two separate barrels. The second barrel is slightly charred on the inside bringing a smoky richness to the bourbon.

If we rushed our distillery visits, we wouldn’t discovered a new favorite bourbon, we wouldn't have met Jimmy Russell, the Master Distiller of Wild Turkey®, we wouldn't have snapped our favorite photos of the Buffalo Trace™ barrel room through less than sneaky tactics and we wouldn't have enjoyed lunch at Wallace Station.

Eat at Wallace Station. No Excuses.

Our Airbnb hosts, Seth and Renee, were more than generous with their knowledge of the Lexington area. Our trip was seamless thanks to them. They introduced us to the deli of our dreams, Wallace Station.

Located on Old Frankfort Pike, this small, established deli packs a punch. The Turkey Rachel, a roasted turkey sandwich generously topped with rich slaw, and the Wallace Cubano, a local slow-cooked pulled pork sandwich with “Pops’ Habagardil sliced pickles,” were devoured. They were delicious; an accurate lunch portion between bourbon tastings. We sat among the white walls plastered with nostalgic photographs and newspaper clippings of the deli’s accolades. The thing I loved most: the roots of the country store which existed prior to the establishment of the deli are still very much alive.


Always Drive the Old Frankfort Pike.

The Old Frankfort Pike is a must-drive back road. Even in March with grey clouds looming, the route, about 17 miles long, was serene. The road showcases the horse country of Kentucky you read about in travel blogs and books. Fog traced the rolling hills with respect. Peaceful, majestic horses peppered the fields. The Old Frankfort Pike made our drive from Lexington to Woodford Reserve® to Buffalo Trace™ smooth and scenic.

The Old Frankfort Pike, recently voted an “essential drive for a U.S. road trip” by National Geographic, became one of our most talked about memories of the trip.  

Wear Comfortable Clothes Made for Standing and Walking.

If bourbon is the heart of the Kentucky Bourbon Trail®, the distillery is the bloodline.

The distillery never stops, always working, pumping. Ben and I were led through working distilleries and barrel rooms, stepping on wooden baseboards and grated floors, scaling alongside copper stills. After each tour, I found myself covered in corn meal or smelling of fermented yeast. It's all a part of the grand experience.

Be sure to wear sneakers or comfortable walking shoes. Pick a lasting layered outfit, one you don't mind acquiring pieces of bourbon makings. I suggest refraining from extra-long black flared jeans (noted for future visits).

Four Roses Distillery

Four Roses Distillery

Woodford Reserve Tasting

Woodford Reserve Tasting

Bourbon Does Not Have to be Your First Love.

Ben and I have a deep love for whiskey, in particular bourbon. On the rocks or neat, it has been our spirit of choice over the past couple of years.

You do not have to love bourbon to appreciate The Kentucky Bourbon Trail®.

Bourbon country has a rich history and rolling, scenic landscapes. How distilleries were formed and then survived prohibition (hello medicinal whiskey!) was fascinating. The distilleries themselves have become historic landmarks. You might not have a taste for bourbon, but it is good to share in the taste for our country's history.

How to Save Money if Bourbon *is* Your First Love.

Following each tour, we were tempted to buy a lot of bourbon.

There is a pure nature to buying a spirit at the place of its birth. If it wasn’t for my husband’s economic conservatism, we would have spent way too much money on spirits we could buy at home.

The majority of distilleries on the The Kentucky Bourbon Trail® are established and well-distributed. You can purchase them from your local liquor stores. We kept our eye out for unique blends or brands, such as Town Branch®, which we have yet to find in western Pennsylvania. Keep cost down by buying bourbon you cannot easily find at home.

It is legal to transport alcohol across state lines for personal use in most states. Alcohol laws vary across states, however. Check your state's’ alcohol laws to be safe.

Woodforde Reserve Tasting Room

Woodforde Reserve Tasting Room

Save Something For Next Time

Following the birth of our first child due in October, Ben and I plan to return to Kentucky to experience more bourbon country and “Kentucky hugs” – the warm burning feeling in your chest following the first sip of bourbon.

It is an artful and welcoming community. Our first trip to The Kentucky Bourbon Trail® gave us a greater appreciation for the work and history behind the crafted spirit. Tapping our glasses, filled with Woodford Reserve® Double Oaked, holds a bit more significance now.

This is a guest post written by Jessa Gibboney.

Jessa Gibboney is a writer based in Pittsburgh, PA. You can find more of her work on her personal website and her blog, Wavy Alabaster, where she discusses sustainable style and the copy of life. Her Instagram is @wavyalabaster.

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