On a quiet stretch of I-64, somewhere between Louisville and Lexington, is Shelby County, one of Kentucky’s best-kept secrets. But this sleepy, rural, historic setting is actually a burgeoning scene of boho boutiques, upscale Airbnbs, a restaurant run by a world-renowned chef, and farms that board and train celebrity horses. Also bourbon. Great bourbon.

If you’re looking for a swanky weekend escape, Shelby County should be at the top of your list. Here’s everything you need to know when planning your stay.

How to Spend a Weekend in Shelby County, KY


Saddlebred Suites

700 Main St. Shelbyville, KY 40065 • (502) 633-0220

Love a modern urban-chic homestay? There is no better place to lay your head than Saddlebred Suites. Thoughtfully designed with comfort and style in mind, these family-owned Airbnbs can house up to 16 people in the combined 3,000 square feet of space, or rent them as individual three-bedroom or studio suites. Situated between trendy downtown boutiques and the best coffee Shelbyville has to offer, it is easy to spend a chill day or two in these beautifully appointed apartments. Want to have a night in and relax for a bit? The suites are equipped with well-stocked kitchens and inviting gathering spaces perfect for groups of all sizes.

Shelby County, Kentucky accommodations

The well-appointed Saddlebred Suites has all the modern conveniences travelers look for in their home away from home.

Saddlebred Suites — Shelby County, Kentucky

The comfortable accommodations make it easy to spend a relaxing day in your suite.

Saddlebred Suites in Shelby County, Kentucky

The details come together to create a space that is both rustic and elegant at once.


Kismet Farm

199 Colt Run Rd, Simpsonville, KY 40067 • (651) 248-2027

Horses and bourbon. That’s what Kentucky does (we’ll get to the bourbon), so no trip to rural Kentucky is really complete without the majestic horses that helped to put the state on the map. Kismet Farm is one of the most iconic locations in Kentucky and THE place for a close encounter. Located in the heart of Simpsonville, a town within Shelby County limits, they offer tours, riding lessons, and train some of the top competitive Saddlebred riders around. It’s also home to celebrity-owned horses (can you say William Shatner?) and the most adorable goats, which are named Maverick and Goose. Book a tour to learn more about show horse life, and then saddle up for a personalized riding lesson.

Kismet Farm in Shelby County, Kentucky

Kismet Farm is a fantastic place to have an authentic Kentucky horse — or goat — encounter.

horse riding at Kismet Farm

Whether you’re an avid rider or have never saddled up, you can enjoy a lesson at Kismet Farm.

horseshoes at Kismet Farm in Shelby County, Kentucky

Shoes off!

Jeptha Creed Distillery

500 Gordon Ln. Shelbyville, KY 40065 • (502) 487-5007

The “from ground to glass” concept is only part of what makes the Jeptha Creed family of spirits so unique. If they can grow it on their 64 acres, they do. What they can’t grow, they buy from other local farms. Another unique fact? This distillery is owned and operated by mother-daughter dynamos Joyce and Autumn Nethery, a rarity in the spirits industry. Their bourbon is aged on-site, plus they also distill vodka, brandy and moonshine. I’m a “bourbon on the rocks” girl, but with flavored varietals like Apple Pie Moonshine and Honey Vodka, there’s something for everyone to enjoy. Don’t forget to check out their free patio concert series and custom cocktail classes while you’re there.

Jeptha Creed — Shelby County, Kentucky

“From ground to glass” is the guiding principle at Jeptha Creed — and it all culminates in a family of delicious spirits.

Jeptha Creed — Shelby County, Kentucky

Get a behind-the-scenes look at the inner workings of Jeptha Creed on a tour, and then, of course, a tasting.

Jeptha Creed — Shelby County, Kentucky

This isn’t your run-of-the-mill moonshine. Enjoy tasty flavors like blackberry, cinnamon or apple pie.

RELATED: Jeptha Creed: One Family’s Scottish Heritage & Kentucky History Distilled

Gallrein Farms

1029 Vigo Rd. Shelbyville, KY 40065 • (502) 633-4849

There is plenty to keep you busy for a day at family-owned and operated Gallrein Farms. Open from spring to fall, kids and adults alike will have fun taking hayrides, mingling with the animals at the free petting zoo, and picking pumpkins or berries depending on the time of year. After a day touring the farm you can snag a light lunch and some homegrown country food staples like ciders and jams. Plant buffs will go wild over their exotic and hard-to-find greenhouse goods.

Pumpkin patch at Gallrein Farm in Shelby County, Kentucky

In the fall, enjoy the seasonal festivities at Gallrein Farms, and don’t forget to pick a pumpkin!

Gallrein Farm in Shelby County, Kentucky

The greenhouse is a great place to discover botanical finds you can take home.

The Polkadotted Pineapple Boutique

536 Main St. Shelbyville, KY 40065 • (502) 437-0418

One trip to The Polkadotted Pineapple Boutique, and you’ll be the odds-on favorite for “Best Dressed” at this year’s Derby festivities. Owner Dori Lewis is a radiant soul with a knack for tapping into her clients’ personal style and bringing it to life in a one-of-a-kind Derby hat. Not sure what to wear yet? Dori stocks exquisite designer dresses — both new and upscale consignment. A one-stop, customized, everything-for-Derby shop? Sign us up!


Get your Derby fascinator at The Polkadotted Pineapple Boutique.


There’s a selection of ready-to-wear hats and fascinators, or one can be customized to your liking.


The Old Stone Inn & Tavern

6905 Shelbyville Rd. Simpsonville, KY 40067 • (502) 722-8200

What do The Old Stone Inn & Tavern, Churchill Downs, five continents, the Olympics and the Super Bowl have in common? World-renowned chef David Danielson, who calls Shelby County, Kentucky “home.” He’s cooked on some of the world’s biggest stages, so it goes without saying that the food he prepares is pretty spectacular. The ambiance of The Old Stone Inn & Tavern is upscale and inviting without a hint of arrogance. The seasonal menu is locally sourced, sometimes even including donated produce from the gardens of nearby residents, and it honors the food — “using every edible part from flower to root and nose to tail.”

Items like portobello mushroom fries and fried green tomatoes will get you started, while entrée options like shrimp & grits and braised lamb ragout will make choosing just one a tough job. If you can’t decide, then let us recommend the mushroom ravioli, which offers an authentic taste of Italy, and frankly, is mind-blowing.

Old Stone Inn & Tavern in Shelby County, Kentucky

Chef David serves up amazing flavors at The Old Stone Inn & Tavern.

Old Stone Inn & Tavern in Shelby County, Kentucky

“Elegant yet approachable” describes the vibe.

Old Stone Inn & Tavern in Shelby County, Kentucky

The menu is replete with Southern fare with an upscale twist.

Historic Science Hill Inn

525 Washington St. Shelbyville, KY, 40065 • (502) 512-3663

Southern charm oozes from every column of Science Hill Inn. In addition to providing a decadent menu of beautifully prepared Southern fare at The Georgian Room, guests can also enjoy a cultural experience via the adjacent Wakefield Scearce Galleries, which house Old English antiques, extremely rare books, art, furnishings, accessories and more.

Science Hill Inn in Shelby County, Kentucky

Science Hill Inn offers both food and some of the finest antiques. Grab a bite and then shop the collections.

The Paddock

700 Main St. Shelbyville, KY 40065 • (859) 445-8319

Rustic charm with a dash of modern, The Paddock is everything you’ll love about Shelby County — all wrapped up in four walls. The Rogers family will make you feel like a regular from the moment you walk through the door, offering options galore to both casual coffee drinkers and connoisseurs alike. (SB TIP: Their house roast is one of the best I’ve ever had! Definitely give it a try!) Pastries and light fare, including gluten-free options, round out the menu of bites, so grab a chair, enjoy your coffee and stay for a while.

The Paddock — Shelby County, Kentucky

The Paddock offers some amazing coffee and small bites. Grab a cup and relax a while.

When you’re ready to start planning your weekend in Shelby County, KY, check out visitshelbyky.com to get started. 

All photography by Jessa Mayhew.


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