Just outside Louisville, discover a side of Kentucky you won’t find in the city! Get up close with Kentucky’s famous horses, sip bourbon down the street from where the grain is grown, and wander through an extraordinary castle garden in Crestwood. Then watch freight trains roll right down the middle of a historic Main Street in La Grange. From unexpected farm tour adventures and one-of-a-kind shopping to memorable dining in places you wouldn’t expect, Oldham County delivers a Kentucky experience all its own. Two days. Countless discoveries. Here’s how to experience the Kentucky found only in Oldham County.
Day 1: Horse Farms, Bourbon, Botanicals & Brews | Crestwood & Goshen
Morning
Start your Oldham County adventure with breakfast at Wilders Cafe in Crestwood. Fuel up with biscuits and gravy, French toast or a hearty breakfast burrito before heading out to explore. For something sweet, order a cinnamon roll or a plate of beignets alongside your morning coffee. It’s a tasty introduction to the local dining scene before a day packed with outdoor adventures.
Welcome to the Farm Tour Capital of Kentucky, where getting up close is all part of the adventure! Explore the entire life of a racehorse through five unique horse farm tours, from adorable baby foals to retired racing legends at two racehorse retirement farms. You can even adopt a retired racehorse! And the adventures don’t stop with horses. Climb aboard a wagon for a bison tour with modern art peppered throughout while overlooking the Ohio River, discover the art of making fresh cheese and yogurt at one of Kentucky’s few remaining dairy farms, or don a beekeeper’s suit and step into the fascinating world of honeybees—or watch the action from a distance!
These aren’t just tours—they’re unforgettable, behind-the-scenes Kentucky experiences that put you right in the middle of the action. Contact the farms directly to book your tours and discover a side of Kentucky most visitors never get to see.
Afternoon
Trade the pastures for colorful blooms at Yew Dell Botanical Gardens, one of Oldham County’s two destinations on the Kentucky Garden Trail. Once the home and commercial nursery of renowned horticulturist Theodore Klein, this beautiful property features thoughtfully designed gardens, winding pathways and a historic stone castle. Explore the ever-changing seasonal displays, admire unusual plant varieties and wander the grounds before stopping at Martha Lee’s Cafe for lunch. Enjoy a bite while taking in views of the castle gardens, one of the property’s newest additions.
Prefer a deli lunch? Red Pepper Deli in Crestwood is another convenient option for sandwiches, soups and a casual midday meal.
Just steps from Yew Dell, get a taste of Kentucky bourbon straight from the source at Kentucky Artisan Distillery, home of Jefferson’s bourbons and many private signature brands. Here, bourbon’s story begins just down the road, where locally grown grain makes its way from nearby Waldeck Mansion & Farm to the distillery. Go behind the scenes to see where the magic happens, from fermentation and distilling to the lab where new whiskey creations take shape. For something extra special, book the Bourbon Clubhouse Barrel Thieving Experience, where you’ll draw barrel-strength bourbon straight from the barrel and taste five distinct mash bills. Settle in with a glass of bourbon by the outdoor firepit or grab a cocktail from the bar and savor a Kentucky experience worth raising a glass to. Reservations are recommended.
Keep the afternoon going with a little treasure hunting at Crestwood Mercantile. Spread across three floors, this shopping destination features more than 80 curated boutique vendors selling everything from vintage collectibles and antiques to clothing, home décor and handmade gifts. It’s also a featured stop along Oldham County’s Thrifting and Antiques Trail, making it an excellent place to find something uniquely Kentucky to bring home.
If you’d rather spend more time outdoors, make the short drive to Goshen for Creasey Mahan Nature Preserve, the county’s other Kentucky Garden Trail destination. With more than nine miles of trails crossing woodlands, wildflower meadows and streams, the preserve offers plenty of room to explore. Follow a pathway to the Frog Pond, admire native plants in the two-acre Woodland Garden, or bring the kids to the accessible Forest Friends Playground. Stop by the Nature Center to discover Kentucky’s biodiversity through interactive exhibits, an indoor beehive, birdwatching opportunities and native wildlife displays. Younger visitors can also explore the Magical Forest Imagination Station. Check the Nature Center’s limited opening hours before visiting.
Evening
As the sun begins to set, head to 3rd Turn Oldham Gardens and spend the evening at Kentucky’s largest beer garden! Spread across 8.6 acres of lush gardens, this one-of-a-kind gathering place invites you to unwind with craft brews, cocktails, great food and live entertainment. Pull up a chair, sample one of more than 20 rotating craft beers or enjoy a handcrafted cocktail while deciding what’s for dinner. A bonus in spring? Cascading purple wisteria creates a spectacular canopy of blooms overhead! Choose from three on-site restaurants—Slice N Dice Pizza, Four Pegs BBQ Smokehouse and The Wager—then settle in for live music or one of the garden’s many seasonal events. It’s one of those places where you come for a drink and end up staying all evening. Check the events calendar to see what’s happening during your visit.
For a more intimate dinner, venture into Goshen for Barn8 Restaurant & Bourbon Bar at Hermitage Farm. Housed inside a beautifully converted horse stable, this distinctive restaurant brings Kentucky’s agricultural roots directly to the dining table. Enjoy seasonal, farm-inspired dishes featuring locally sourced ingredients, including produce grown on the property, alongside craft cocktails and Kentucky bourbon.
Staying closer to Crestwood? Crestwood Bistro offers another dinner option, with elevated takeout that makes it easy to enjoy a quieter evening after a full day of sightseeing.
Why settle for an ordinary overnight stay when you can sleep on a Kentucky horse farm? Oldham County’s five horse farm bed-and-breakfasts offer a one-of-a-kind experience, where horses may be grazing just outside your window and mornings begin with beautiful views of Kentucky’s famous bluegrass. Enjoy warm hospitality and a home-cooked breakfast, distinctive accommodations, and a relaxing start to another day of Oldham County adventures.
Day 2: Trains on Main, River Towns & Quarry Swimming | La Grange & Westport
Morning
Begin your second day with a sweet stop at Dough Baby Donuts, a locally owned bakery in La Grange. Pick up freshly made doughnuts and other baked treats before exploring downtown. Arrive early for the best selection, as popular varieties can sell out. If you want something to sip while you explore, head to La Grange Coffee Roasters for a handcrafted coffee.
With breakfast taken care of, it’s time for one of Kentucky’s most unusual downtown experiences. In historic La Grange, freight trains travel directly down the middle of Main Street, passing brick storefronts, boutiques and restaurants just feet away. Known as Trains on Main, this remarkable spectacle draws visitors hoping to catch a passing locomotive in action. Head to the train observation tower for a great viewing spot, then browse the independent shops and galleries lining Main Street. You might hear the crossing bells before you see the train, so have your camera ready!
Continue your railroad adventure at the La Grange Railroad Museum & Learning Center, housed in a historic L&N Train depot dating to 1914. Explore exhibits documenting the region’s railroad history, including artifacts from the era when interurban trolleys connected La Grange and Louisville. Outside, admire historic railcars, including a 1929 Louisville & Nashville dining car, a vintage caboose and a steam locomotive built in England. Model railroad enthusiasts will also appreciate the museum’s elaborate working train layouts.
Afternoon
Before leaving downtown, visit the Oldham County History Center to uncover the region’s fascinating past. Just a block from Courthouse Square, the history center’s campus features three historic buildings, a cellar from the Peyton Samuel Head home, a Colonial garden and the Dahlgren Pioneer Barn. Explore exhibits filled with photographs, artifacts and interactive displays that bring Oldham County’s history to life, from its early settlers to its connections with the Underground Railroad. Stop by the J.C. Barnett Library & Archives to discover historical records and stories preserved for future generations. The archives are also recognized as a National Park Service Network to Freedom site for documenting the region’s Underground Railroad history.
For lunch, take a scenic detour toward the Ohio River and the tiny community of Westport, home to Knock on Wood Country Mercantile & Cafe. This charming destination combines a country-style café with a gift shop filled with rustic home décor and locally inspired finds. Order a chicken salad croissant, homemade soup or quiche, then save room for a slice of towering cake or pie.
If you’re visiting between late May and Labor Day, consider swapping part of your afternoon for a refreshing dip at Bluegrass Spring Quarry, just outside La Grange. This adults-only swimming destination features striking blue water in a former rock quarry more than 55 feet deep. Spend a few hours floating, swimming and soaking up the sunshine in one of Kentucky’s most distinctive swimming spots. Admission is ticketed, and advance reservations are recommended.
Evening
Return to La Grange for dinner at Madeline’s Nibbles & Wine in the historic downtown district. With a menu inspired by European flavors and a focus on fresh ingredients, it’s a great choice for celebrating the final evening of your Oldham County getaway. Start with a selection of cheeses or antipasto, then enjoy dishes like shrimp scampi, pasta carbonara or house-made Italian meatballs. Pair your meal with a glass of wine, then finish with cannoli or an affogato.
If you’re not quite ready for your two-day adventure to end, catch a movie under the stars at Sauerbeck Family Drive-In. This modern take on a classic American pastime features a giant 98-foot diagonal screen, 4K digital projection and sound transmitted through your car’s FM radio. Grab popcorn and your favorite movie snacks from the concession stand, get comfortable and enjoy a night at the movies without ever leaving your vehicle. Screenings are seasonal and generally run through November, so check the current schedule before you visit.
Two days in Oldham County are just enough to get a taste of what makes this corner of Kentucky so unexpected. From bourbon straight from the barrel and horses you can actually meet, to trains rolling down Main Street and swimming in an adults-only spring-fed quarry, these are experiences you won’t find just anywhere. And with so much more waiting beyond this itinerary, one thing is certain: two days won’t be enough. Come find your Kentucky. Only in Oldham.
