Most unique places to stay on the Bourbon Trail
As a native Kentuckian, I’ve spent a lot of time at bourbon distilleries. In fact, I was even married at one! And through my experiences I’ve learned a lot about what makes the best distillery tours, unique places to stay, and experiences worthwhile.
That’s why I know Shelby County is the best jumping off points for any trip on the Bourbon Trail. Why? It’s centrally located to be closest to every distillery, has the most unique places to stay and interesting things to do on the trail. And as someone who grew up in Shelby County, I can promise you that you won’t be disappointed.
This post is a paid collaboration between Kendyl Travels and ShelbyKY Tourism. However, this post reflects my personal opinions.
When should I visit the Kentucky Bourbon Trail?
The Bourbon Trail can be visited anytime of the year. With most distilleries open year-round, you can book a tour anytime with just a few holiday exceptions. However, due to Kentucky’s weather extremes, some times of year are just more pleasant to be outside on a walking tour than others.
Spring and fall are the best times to have the great weather for tours that include outdoor operations (most do). Summer and fall are also the busiest times to visit the Bourbon Trail, so book your tours well in advance. And though it can be cold, winter is a great time to visit to have limited tourists and cozy fires roaring inside visitor centers across the region.
How long is enough time to spend on the Bourbon Trail?
I’d recommend spending at least 3 days on the trail to get the most out of your experience. Most people travel here for a long weekend but you can easily find enough to do for a 5-day or 7-day itinerary, especially if you venture off the Bourbon Trail to one of the many other things to do in Kentucky.
>> Don’t miss my 3-day bourbon trail itinerary!
Where should I stay on the bourbon trail?
Kentucky is home to 95 bourbon distilleries, with only a handful on the official Bourbon Trail and Craft Trail. It’s no wonder it can be overwhelming to figure out where to stay. Most people end up driving around the many distilleries in bourbon country, spending upwards of 1.5 hours getting to a distillery area every day. That’s a lot of driving.
So, where should you stay?
Because you’ll likely be driving between your destinations throughout your trip, I recommend staying in Shelby County while visiting the trail. Why? Shelby County is centrally located to be the closest distance from every distillery on the trail. And it’s home to two of its own distilleries! That means you’ll spend less time driving the trail and more time enjoying it.
Check out my list of the most unique places to stay on the Bourbon Trail below!
Shelby County: Best hotel, bed and breakfast and Airbnb options
Shelby County is home to some of the most unique places to stay on the Bourbon Trail that make you feel like you’re a true Kentuckian. Plus, you can easily visit both Bulleit and Jeptha Creed in town.
You can find a complete list of vacation rental options on ShelbyKY Tourism’s website. But here are some of my favorite unique stays:
Explore downtown Shelbyville in a refinished loft
With many beautifully designed options right in downtown Shelbyville, you’ll find the best of both worlds: walkability to shops and restaurants and a unique stay perfect for Instagram. I love this industrial loft for a couple but if you’re traveling with some friends this loft is the perfect option!
Travel Tip! Book with VRBO and earn OneKeyCash you can use towards future stays. Even better? You can book your stay through United’s shopping portal to earn points towards free flights.
Host all your friends in this renovated 1909 house
Bringing a big group to the trail? The Cooper and Oak is a great option that includes elevated finishes and historic charm. The home can host up to 8 people. And with 4 bedrooms, 4 bathrooms, and two kitchens you’ll have plenty of space for everyone to spread out after a long day of touring.
Spend your trip in a quaint lakeside cabin
Chickapoo Farm’s Ripple Cabin might just be the best little gem on the trail. This cedar cabin includes all your necessary amenities in the countryside. Plus the farm includes a Pick Your Own Experience, where visitors can create and cut their own flowers and herbs from the garden. The ability to pick your own flowers makes this one of the most unique places to stay on the Bourbon Trail.
Enjoy a local horse farm at the best bed and breakfast on the Bourbon Trail
What makes a bed and breakfast experience great in Shelby County is the ability to go outside and see the rolling hills and horse farms surrounding you. That’s why I love the Cerulean Farm. This 1860 homestead is truly a unique experience on the trail. You can easily add-on horse tours and hands-on experiences to your stay to get a real Kentucky experience.
If horse farms aren’t your thing, Shelby County is home to a few other bed and breakfast options.
Get out in the countryside at a working farm stay
One thing that’s clear when driving Bourbon Country is how beautiful the countryside is. That’s why I’m a huge fan of farm stays in Kentucky. The Walnut Grove Farm and Lodge offers you a chance to stay out of town and enjoy the quieter and slower Kentucky countryside.
Best things to do in Shelbyville, KY
Visit Jeptha Creed and Bulleit bourbon distilleries
Shelby County is home to two bourbon distilleries. Both distilleries offer more than standard tours, too. Bulleit’s elevated tasting and cocktail making classes are a great alternative to standard tours.
Jeptha Creed takes farm-to-table to bourbon. With all the ingredients coming from the family farm, you’ll certainly have a unique experience. You can do a tasting for free. But consider a barrel tasting experience or mixology class for a more unique experience.
What are the best tours on the Bourbon Trail? Check our my complete guide!
Go horseback riding at the Red Fern Riding Center
You cannot go to Kentucky and not think about horses. So why not go riding at Red Fern Riding Center? Here you can take the scenic way through the winding terrain at Shelby Trails Park. It’s a great way to get to know a little about horse culture and ride along the scenic countryside.
Shop downtown Shelbyville for local products
With many unique local shops, you’ll certainly find something special to take home with you.
Learn about Icelandic horses at Lettleiki Icelandics
Probably one of the most unique experiences in Shelby County is visiting the largest Icelandic horse farm outside of Iceland. Tours will give you a bit of history about the horses and lead you through their facilities.
Where to eat in Shelbyville, Kentucky
From authentic international meals to some of the best southern food in Kentucky, you’ll find plenty of good eats. Here are a few of my top recommendations:
Bell House
One of my personal favorite places for southern food is Bell House. Be sure to make reservations. Though everything is great, my go-to is their Kentucky Hot Brown. A hot dish of melted cheese served atop tomato, turkey, bacon, and bread… this Kentucky classic is something not to be missed while on a trip to Kentucky.
McKinley’s Cafe
I’m not going to lie when I say this is the place I always visit when I’m in my hometown. McKinley’s has been a staple of downtown Shelbyville for what feels like forever. Stop by for an incredible lunch of sandwiches and their famous chili.
Weathered Oak Farms
The best cinnamon rolls money can buy – be sure to visit Weathered Oak Farms for a coffee and pastry before setting off for a day of tours. The small bakery also includes great local gifts, like honey, pottery, and aprons.
Sixth and Main Coffee House
Located in the heart of downtown Shelbyville, you’ll find plenty of locals enjoying their morning coffee while reading the newspaper in this no-frills coffee shop that hasn’t changed its interior in 20 years.
Channel Catfish House
Located on the Guest Creek waterfront, enjoy a local piece of catfish or perhaps their incredible burgers.
PRO TIP! Located just minutes from Bulleit Distillery, you can easily visit Channel Catfish House before or after your visit.
La Fogata
There are so many amazing places for authentic Mexican tacos and other dishes in Shelby County. La Fogata is just one of many worth trying. I love their taco de carnitas but their sopes and moles are popular among locals, too.
B&N Food Market
Located on your way to visit Buffalo Trace, be sure to stop for one of the most amazing burgers you’ll ever have. (Seriously, it’s consistently voted the best burger in Shelby County.)
More Bourbon Trail Tips + Inspiration
I hope you enjoyed learning more about some unique places to stay on the Bourbon Trail! Here are some other posts to help you plan your trip to Kentucky:
- Don’t miss my complete guide to visiting the Bourbon Trail (it answers all your questions)
- Want to learn more about all your distillery options? Use my free interactive map
- Need to have some ideas on the best distilleries to visit? Use this
- If you’re spending some time in Louisville be sure to check out my Urban Bourbon guide, too
