I’m a day behind in my chronicle of our Bourbon Trail adventure, so it’s time to play a little catch-up. Rather than a strict daily diary, I’m going to group our experiences by activity. It’s been a whirlwind trip so far, filled with great friends, fantastic bourbon, and a few welcome surprises.

Getting There is Half the… Challenge?

The journey began with a bit of a hiccup. My Tuesday night flight from Jacksonville was scheduled to depart at 8:10 p.m., but the domino effect of an earlier plane swap in San Diego meant our aircraft didn’t even arrive in Jax until after 9:20 p.m. We finally took off close to 10:00 p.m., which meant my best friend, Scott, and I didn’t hit the road from Nashville until after 10:30 p.m. Central Time. By the time we checked into our hotel in Elizabethtown, Kentucky, it was 2:00 a.m. Eastern.

I can’t fault Southwest Airlines for the delay; these things happen. In fact, kudos are due to our flight crew, whose easygoing and fun demeanor made a stressful situation much more pleasant.

A Trio of Excellent Hotels

We’re on our third hotel in as many nights, and each one has been excellent in its own way.

• Baymont by Wyndham (Elizabethtown): This was purely a place to crash for about six hours. We barely experienced it, aside from the beds doing their job wonderfully. I managed to scarf down some eggs and ham and grab a few waffle medallions for the road. It provided a much-needed rest to start our journey.
• Capitol Plaza Hotel (Frankfort): We had more time to appreciate this hotel. The lobby is gorgeous, greeting guests with a beautiful waterfall. Our rooms were spacious and comfortable with wonderful views. It was here that our friend Austin’s room became the setting for our first blind tasting of the trip.
• Distill Inn (Bardstown): This place is a real gem. It strikes a perfect balance between rustic charm and modern comfort, making it the most comfortable stay so far. Just past the check-in desk sits a small bar with an impressive selection of bottles. Scott’s and my room pulled double duty as our restaurant for the night and the venue for our friend Tim’s blind tasting. After another great night’s sleep, the smell of breakfast is fortifying us for the day ahead.

The Main Event: The Tours and Distilleries

Old Forester: Scott and I started Wednesday in Louisville, and our tour at Old Forester set an incredibly high bar. Our guide, Trish, was a fountain of knowledge, leading us through the history of bourbon, in which Old Forester is a foundational player. We got a behind-the-scenes look at their distilling process, from the massive column still—affectionately named “Big Penny”—to the fermentation vats where the intoxicating aroma of the mash hung heavy in the air. We saw their on-site cooper charring a new barrel to perfection and watched the bottling line fill gorgeous single-barrel bottles. The tour concluded with a tasting of their 1870, 1897, and 1910 expressions, plus a sample of the 117 Series “1910 Extra Old.” It was so good, I had to buy a bottle. We lingered at the bar for a flight of another 117 Series, the legendary Birthday Bourbon, and the President’s Choice. The Birthday Bourbon was everything it’s reputed to be: creamy, complex, and leaving a finish that you wish would never end.

Evan Williams: This stop was an unscheduled detour that turned into a highlight. With no tours available, we browsed the gift shop and had the pleasure of meeting Jodie Filiatreau, their artisanal distiller for the Square 6 line. He graciously poured us tastes of all three expressions and explained their unique qualities. Scott left with the wheated bourbon, and I grabbed the high-rye. Upstairs in the bar, our hostess Shannon set us up with two blinds and other Evan Williams samples. It was at this moment that Scott and I realized some of the best experiences are the ones you don’t plan.

Bulleit: Our fun at Evan Williams made us late for our tour at Bulleit, but they kindly included us in the post-tour tasting. The hospitality was wonderful, and we learned a great deal about the brand while sampling their excellent bourbon, including a fantastic single-barrel expression.

Buffalo Trace: On Thursday, Scott, Tim, and I (our friend Austin having headed back to St. Louis) started our day at the legendary Buffalo Trace distillery. Our guide, Ed, gave us a first-rate tour focused heavily on the life of a barrel, from its arrival on the “railroad” to its time in the massive rickhouses. We even saw barrels that survived the recent flood, their precious contents apparently unharmed. The tour ended with a great tasting that surprisingly started with Wheatley Vodka—so smooth it tasted like pure water. We didn’t have much time, but we did get to snap a picture with the one and only Freddie Johnson, a true icon in the bourbon world.

Four Roses: From there, we zipped over to Lawrenceburg for a single barrel tasting at Four Roses hosted by our Four Roses guide, Win. It was an intimate experience with just the three of us. We sampled four of their best 100-proof single barrels, culminating in my favorite of the day: the OESO. This fruit-forward bourbon is always a delight and was the perfect end to our visit.

Wild Turkey: Our last stop of the day was a quick drive around the corner to Wild Turkey. We were hoping for a glimpse of the master, Jimmy Russell, and while he wasn’t there, we did see his dedicated parking space. The grounds are first-rate, and I wish we’d had more time to soak it all in.

Fueling the Journey

While bourbon was the star, the food has been an unexpected hero. Wednesday night’s dinner at The Brown Barrel was a fantastic local find where every dish hit the spot. The real standout, however, was Taylor Belle’s & Burgers in Lawrenceburg, where we had lunch in Thursday. I had their weekly special, the Bourbon Street Burger, with sautéed onions, mushrooms, and a bourbon glaze. It was absolutely delicious—I wish there was one in Jacksonville! Last night, exhaustion won out, so Tim grabbed a couple of pizzas from Cafe Primo in Bardstown. The meat lover’s and buffalo chicken pizzas were the perfect, satisfying end to a long day.

The Blind Leading the Blind

Austin’s Sazerac Blind: On Wednesday, Austin kicked things off with a blind tasting of five Sazerac products. I was stunned that Stagg Jr., one of my all-time favorites, finished third on my list. It was no surprise, however, that the legendary Weller Antique 107 claimed the top spot.

Tim‘s Rye Blind: Last night, Tim led a blind tasting featuring mostly 100-proof rye whiskeys. It was another fantastic lineup with some very interesting results. The top three in his five-dram blind were all things I’d never had before. The best of the best was High West’s Midwinter Night’s Dram, which was an apple cinnamon delight. Second was the George Dickel 3-Chamber Leopold Brothers Rye. And third was Angels Envy’s Caribbean Rum finished rye. Even though this one didn’t win, it was the biggest surprise in an interesting whiskey that had notes of maple, smoke and barbecue. I would love to spend more time drinking that one figure out what makes it tick.

That’s the trip so far! It’s been an incredible mix of history, hospitality, and phenomenal spirits, made all the better by sharing it with great friends. Today will be spent exploring more of what Bardstown has to offer before we head back to Louisville for Saturday and our final two nights. On to the rest of the adventure!