November in Kentucky feels cinematic, cool air, bare trees, and soft golden light that makes everything slow down just enough. For our anniversary weekend, my partner and I chose Bardstown, Kentucky, a town that wears its bourbon identity proudly and makes exploring the Kentucky Bourbon Trail both effortless and immersive.
With Bardstown as our base at this adorable Airbnb, we spent two days weaving together historic distilleries, contemporary art, small-batch craft bourbon, and some of the most iconic scenery in the Bluegrass State. Here’s how to spend a weekend touring the Kentucky Bourbon Trail.
Why Bardstown Is the Perfect Bourbon Trail Home Base
Watch this video for a short overview, then read the blog for full details.
Often called the Bourbon Capital of the World, Bardstown, Kentucky combines small-town warmth with deep bourbon roots in a way that feels authentic rather than touristy. Historic buildings line the downtown streets, many dating back to the late 1700s, giving the town a lived-in, timeless quality that pairs naturally with the idea of bourbon aging patiently nearby.
What makes Bardstown especially appealing is how easy it is to settle in. The downtown area is compact and walkable, with locally owned restaurants, tasting rooms, and shops that invite lingering rather than rushing. Even in November, there’s a gentle hum to the town with locals chatting at dinner, visitors swapping distillery recommendations, and the sense that bourbon here isn’t just an attraction, it’s part of daily life.
Staying in Bardstown at this cute Airbnb meant we could return each evening without feeling wrung out from driving. After full days of tours and tastings, it was grounding to come back to a place that felt calm and welcoming.
Day One: Castle & Key and Maker’s Mark Distilleries
Castle & Key Distillery (Frankfort)
One of the highlights of our visit to Castle & Key was how much freedom there was to explore. Castle & Key did not offer tastings during our visit; however, we also did not need a ticket or a reservation to enter the grounds. We were able to wander at our own pace, which made the stop feel more relaxed than a traditional tour-only experience.
The property sits along Glenn’s Creek and includes walking paths, a restored springhouse, landscaped gardens, and multiple vantage points to view the historic castle-style buildings. Even in November, the grounds were well-maintained and easy to navigate, making it a good stop if you enjoy spending time outdoors, relaxing with a cocktail (who doesn’t?)
While they did not offer tastings, Castle & Key did offer cocktails made with their own bourbons, which gave us a chance to sample their spirits in a different format. The cocktail menu changes seasonally, and it’s worth planning extra time to enjoy a drink outside and explore the grounds rather than rushing to the next stop.
Bourbon After Dark at Maker’s Mark
That evening, we headed to Maker’s Mark at Star Hill Farm, a place that already holds personal meaning for me thanks to my past brand ambassadorship with Maker’s Mark. Because of my past ambassadorship, we had been on their tour and tasting many times, and we decided to do something new during this visit.
That evening, we booked tickets for the special event: Chihuly glass installation after dark. Dale Chihuly’s work, known worldwide for its scale, movement, and color, has a long-standing relationship with Maker’s Mark. What began with a dramatic permanent installation inside a barrel room evolved into large-scale pieces placed throughout the distillery grounds.
At night, the glass glows, pathways feel quieter, colors feel deeper, and the entire distillery takes on a dreamlike quality that’s equal parts art exhibition and bourbon pilgrimage. It was romantic, surreal, and absolutely unforgettable. The evening ended with music and specially made cocktails featuring Maker’s Mark.
Day Two: Preservation and Woodford Distilleries
Tour and Tasting: Preservation Distillery (Bardstown)
Preservation Distillery is a women-owned craft distillery built around small-scale production and traditional methods. Operating in one- to three-barrel batches, the distillery focuses on control and experimentation rather than volume.
Tours here feel intimate and personal, and the setting reinforces that ethos. Our group was small and our guide even smaller, but energetic and passionate as heck! The distillery sits on a working farm, home to longhorn steer that play a role in their sustainable approach to production. There was even an adorable newborn calf there to greet us. Out of all the bourbons we sampled this weekend, these were my favorite.
Note: This distillery does require a reservation for a tour, so visit their website and book yours in advance.
What to expect from the tasting at Preservation:
- A guided sampling of multiple Preservation expressions
- Clear explanations of how small batches affect flavor and consistency
- Time for questions and comparison between pours
The tasting feels informal and educational, making it a good contrast to larger, more polished Bourbon Trail experiences.
Day Two Afternoon: Woodford Reserve Food and Bourbon Pairing
Our final stop took us into Woodford County, where bourbon and horse culture share equal billing. Woodford Reserve Distillery delivers one of the most polished and educational tours on the trail, walking visitors through history, process, and tasting with clarity and intention.
Our tour at Woodford Reserve included a guided food pairing, which added another layer to the tasting. Each bite was selected to highlight specific flavor notes in the bourbon, making it easier to identify how sweetness, spice, and oak shift depending on what you’re eating. It was a useful, approachable way to understand Woodford’s flavor profile without feeling overly formal.
The drive itself is part of the experience. Rolling past stone fences, open pastures, and legendary horse farms, this stretch of Kentucky feels iconic for a reason. Even without stopping, the scenery invites you to linger, slow down, and take it all in.
Go or No? What Made This Anniversary Weekend Trip Special
- A perfect balance of iconic distilleries and craft producers
- Experiencing Maker’s Mark and Chihuly glass after dark
- Staying in Bardstown, where bourbon culture feels lived-in, not staged
- Unexpected moments—like meeting a brand-new longhorn calf
This wasn’t just a bourbon weekend. It was a reminder of why Kentucky is so special: the land, the craftsmanship, the art, and the stories unfolding quietly in between.
Know Before You Go
Driving Times (Approximate)
Some of these distilleries are an hour or more away from each other. Build in time and plan your itinerary in advance, including booking your tour reservations on the distillery websites. Keep in mind these driving times and booking tips for a smooth, stress-free weekend.
- Bardstown → Maker’s Mark (Loretto): 25–30 minutes
- Bardstown → Preservation Distillery: 10–15 minutes
- Bardstown → Castle & Key (Frankfort): 55–60 minutes
- Bardstown → Woodford Reserve (Versailles): 45–50 minutes
Distillery Tour Booking Tips
- Reserve tours in advance, especially for Maker’s Mark and Woodford Reserve. Weekends fill quickly, even in the off-season.
- Check evening event schedules at Maker’s Mark if you’re hoping to see Chihuly installations at night.
- Build in buffer time between tours. Distillery grounds are often as memorable as the tastings.
- November weather can shift quickly; layers and comfortable shoes are essential.
If you’re planning a short Bourbon Trail trip, especially for a celebration, this combination of stops offers variety, manageable driving times, and a strong sense of place. It’s proof that you don’t need to pack in every distillery to have a memorable experience; choosing a thoughtful mix and allowing time to enjoy each one makes all the difference.
Off Duty Traveler 