Our Journey Along the Bourbon Trail
- G. Rhodes
- Sep 20
- 6 min read
After a good night’s sleep at Lexington's Manchester Hotel, we were well rested come Friday morning. The group was eager to continue exploring our take on the Bourbon Trail, which is actually a curated collection of distilleries throughout Kentucky, rather than a single defined path. The Kentucky Bourbon Trail is a tourism program developed by the Kentucky Distillers’ Association that allows visitors to tour and taste bourbon at a collection of distilleries across the state, highlighting the history and craftsmanship of America's native spirit. Launched in 1999 to boost tourism and educate visitors about Kentucky's bourbon heritage. the trail includes both major legacy distilleries and smaller craft operations, offering tours, tastings, and unique visitor experiences.
We first drove to the Castle & Key Distillery in Frankfort. Our expert tour guide Molly explained that it was originally built in 1887 by bourbon visionary Colonel E.H. Taylor, Jr. The site, then known as the Old Taylor Distillery, was the first of its kind to be designed as a tourist destination. Taylor built a grand, castle-like complex complete with lush grounds, including a sunken garden and a Roman-bath-style springhouse. After Prohibition forced the distillery to close in 1920, the site changed hands several times and was ultimately abandoned in 1972. It sat in ruins for over 40 years, becoming overgrown with vegetation and falling into disrepair. In 2014, a group of partners purchased the property and began a multi-year, multi-million-dollar restoration project, which carefully preserved the historic architecture while revitalizing the grounds, bringing the colonel’s original vision back to life. We learned that Castle & Key is committed to producing all of its spirits, including bourbon, rye whiskey, and gin, from scratch using locally sourced grains. This "grain to glass" approach ensures meticulous quality control over every step of the process. When the tour was over, we went up to the Tasting Lab, located inside the Octagonal Tower, a structure once housing Colonel Taylor's yeast propagation laboratory. Here, Chris walked us through a tasting of their Rise Gin, Small-Batch Traditional Bourbon, Small-Batch Wheated Bourbon and Restoration Rye. Some samples tasted better than others, but it was all part of the shared experience.
With a quick bite under our belts from a food truck on property, we traveled a few miles south to the Woodford Reserve complex in nearby Versailles. This was a very impressive place! From the lovely waiting room, our guide Bethany directed us to a spotless shuttle bus, which took us a short distance downhill to the actual distillery. It’s on a National Historic Landmark site, and our tour showcased buildings from the 19th, 20th and 21st centuries that are still in use today. Woodford Reserve is the only major distillery to use three copper pot stills for its whiskey, a rarity in the industry and a signature process that contributes to its balanced flavor. We were also granted an opportunity to visit one of the only heat-cycled barrelhouses in the world, where their barrels were stored to age the bourbon. Our tour culminated in a guided tasting. Here, we experienced the nuances of Woodford Reserve's flavors highlighted by a guided food pairing, including Aged Parmesan Cheese, Toasted Hazelnut, Dried Cranberry, Orange, and Dark Chocolate. They were designed to highlight specific flavor notes such as wood, nuts, fruit, and cocoa within the bourbon. Each sip was meant to be a "Spectacle for the Senses" revealing its complex profile. It also provided an opportunity for us to experience several of their award-winning whiskeys before returning to Lexington. We loved it.
Drinks at the Granddam Lounge preceded Friday evening’s dinner at Frank & Dino’s. With numerous photos of the famous crooners adorning the walls, this upscale Italian restaurant is known for its classic cuisine, fun atmosphere and lively entertainment. The restaurant brings a taste of New York's sophisticated, high-energy fine dining to the heart of Kentucky. This is delivered through a lively bar scene, classy décor, and an upbeat ambiance. Matt was our server and he took excellent care of us that evening. The restaurant specializes in Southern Italian fare, with authentic and flavorful dishes. I thought the Chicken Parmesan was okay, but the others raved about their Salmon and Spaghetti Bolognese dishes and we all agreed that the portion sizes were more than adequate. We took advantage of the complimentary hotel shuttle both going and returning from Frank & Dino’s and made fast friends with Jason, our driver who seemed to know just about everything there was to know about Lexington.
For a change of pace on Saturday, we chose to visit the small Barrel House Distilling Company just a few blocks down the road from the Manchester Hotel. It’s located in the historic barreling house of the original James E. Pepper Distillery which operated in Lexington until 1968. Barrel House is known for producing small-batch spirits using locally-sourced ingredients and traditional methods. As a part of the tour, our guide Jeff related an interesting story. During Prohibition, physicians could legally prescribe alcoholic beverages like whiskey for medicinal purposes, which was a major loophole in the ban on alcohol. Patients with prescriptions from doctors on government-issued forms could legally obtain a limited amount of alcohol from a pharmacy, typically a pint of whiskey every ten days. We each received a “Prescription Form for Medicinal Liquor issued under the authority of the National Prohibition Act.” It entitled us to $1.00 off our “prescription” for a drink at the on-site Elkhorn Tavern. I thought that was a clever way to encourage guests to stick around at the tavern after the tasting, during which we enjoyed a sampling of their RockCastle Bourbon, Pure Blue Vodka, and Devil John Moonshine. Barrel House also maintained a small gift shop at which visitors could purchase their spirits as well as other bourbon-themed items.
Our final dinner in Lexington was held at the storied Dudley’s on Short Restaurant located in a historic 1889 building that was once the prominent Northern Bank, a Lexington landmark. The restaurant is known for its award-winning American cuisine, its charming atmosphere steeped in tradition, and its focus on local ingredients. Upon entering, we passed a very busy bar area and were then escorted upstairs to a lovely, quiet room with a nice round table. Our server Joanie was attentive and, paying homage to the locale, I ordered a Woodford Manhattan. Although I didn’t specify, I was surprised the drink was served straight up, but must admit it was very tasty. The Tournedos of Beef were done to a turn, accompanied by Mashed Potatoes and Green Beans and paired with a very good St. Francis Sonoma County Cabernet Sauvignon. All of us thoroughly enjoyed our dinner and once again enlisted Jason to provide the evening’s. transportation. After a brief nightcap at the Granddam Lounge, we called it a day.
With the rental car all packed up, we checked out of the Manchester Hotel on Sunday morning and headed straight for the Cincinnati Airport. We opted to depart from there in order to catch a non-stop flight back home to Raleigh. We made the right decision after the hectic scene we faced in Atlanta on the outbound when our first flight was delayed. Maybe it was because we’d been eating so well on this trip that our stomachs began grumbling around the noon hour. In any case, we decided to stop at the historic Tousey House Tavern in Burlington, Kentucky and it proved to be an unexpected find. The building housing the restaurant dates back to the early Nineteenth Century and we could tell it’s been well cared for. Our group was escorted upstairs and arrived just in time for Sunday brunch and we thoroughly enjoyed their breakfast take on southern-style cuisine. From there, it was a quick nine miles to the airport where we returned the rental car and checked in for what proved to be a quick and uneventful flight home.
We had a wonderful trip! There’s something to be said about the stronger bonds formed with good friends while traveling together and the fond memories that stay with us long after our return.
Until next time…safe travels.