Just outside Louisville, Oldham County serves up a Kentucky getaway filled with horse farms, bourbon tastings, beautiful gardens and a historic downtown where freight trains rumble straight down Main Street. Spend one day exploring Crestwood’s countryside attractions, then head to La Grange for railroad history, small-town shopping and memorable local eats. With a few unexpected adventures along the way, here’s how to spend two days in Oldham County, Kentucky.
Day 1: Crestwood & the Countryside
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.
Next, discover why Oldham County proudly calls itself the Farm Tour Capital of Kentucky. With Oldham Farm Tours, visitors can get an up-close look at Kentucky’s agricultural heritage through interactive experiences at working farms. Meet beautiful horses at one of the county’s five horse farms, learn about life on a working dairy farm or explore other agricultural experiences that go well beyond admiring animals from behind a fence. Depending on your chosen tour, you might find yourself feeding friendly farm animals, learning about horse care or discovering how local farms bring food from pasture to plate. Reservations are recommended, and experiences vary by farm and season.
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.
Before leaving the area, head next door to Kentucky Artisan Distillery for a behind-the-scenes look at bourbon production. This working distillery is home to Jefferson’s Bourbon and several other brands, giving visitors a chance to see the process from grain to bottle. Guided tours bring you close to the fermentation equipment and production areas, including the laboratory where the team explores new whiskey ideas. Finish with a tasting, or upgrade your experience at the new Bourbon Clubhouse, where barrel tastings highlight five different whiskey mash bills. Book ahead to secure your preferred experience.
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
Wrap up your Crestwood adventures at 3rd Turn Oldham Gardens, home to Kentucky’s largest cultivated beer garden and one of the country’s largest. Spanning 8.6 acres, this charming, rustic gathering spot combines lush greenery, craft beverages, delicious food and plenty of entertainment. Choose from a rotating selection of more than 20 craft brews, including seasonal favorites and exclusive small-batch releases, or sip a handcrafted cocktail featuring fresh, local ingredients. When hunger strikes, choose from three on-site restaurants: Slice N Dice Pizza, Four Pegs BBQ Smokehouse and The Wager. Live music brings local talent to the stage on weekends, with everything from folk to jazz, while seasonal festivals feature local artisans, food vendors and family-friendly activities. 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.
For an overnight stay with plenty of Kentucky character, consider one of Oldham County’s horse farm bed-and-breakfasts. These countryside accommodations trade ordinary hotel surroundings for peaceful farmland, welcoming hospitality and mornings spent among the rolling hills of horse country. Many include breakfast, making it easy to get an early start on tomorrow’s adventures.
Day 2: La Grange & Beyond
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.
From bourbon tastings and beautiful gardens to the thrill of watching a freight train roll down Main Street, Oldham County offers plenty of reasons to make a trip of it. With even more farm tours, countryside escapes, and small-town discoveries waiting beyond these two days, you may find yourself planning your next visit before you head home.
