The Ultimate 7-day guide to the Kentucky Bourbon Trail featuring iconic distilleries, luxury hotels, historic towns, and top dining across Louisville, Bardstown, and Lexington.
Kentucky doesn’t just make bourbon—it breathes it. Out here in the Bluegrass heartland, where the hills roll soft and the air carries a whisper of oak, the landscape feels designed for amber spirits. The limestone-water that runs beneath these fields, the cool barns tucked between hardwood forests, and the families who’ve been distilling for generations—this is the quiet alchemy behind one of America’s most storied drinks.
The Kentucky Bourbon Trail, now in its twenty-sixth year, has grown into something larger than a route—it’s a pilgrimage. The original trail winds through heritage distilleries with names etched into bar shelves across the world, but the journey has branched into intimate side roads too. There’s the Kentucky Craft Trail for small-batch obsessives, the Urban Bourbon Trail in Louisville for those who prefer their tastings with cocktails and city buzz, and just across the river, Northern Kentucky’s B-Line—a collection of bourbon bars and craft stops adding a fresh edge to the tradition.
Whether you’re drawn to polished visitor centers or tucked-away rickhouses perfumed with aging whiskey, bourbon is your guide to understanding Kentucky’s rhythm. Here’s how to plan your route—where to sip, linger, wander, and stay—depending on the mood of your trip, be it city-spirited or country-deep.
Road Trip Overview
The Kentucky Bourbon Trail unfolds like a daydream through the Bluegrass countryside. Picture a wide triangle linking Louisville, Bardstown, and Frankfort—each point a different flavor of the state’s bourbon soul. The roads between them are gentle and scenic, rolling past horse farms with postcard-perfect paddocks, small towns steeped in Southern lore, and distilleries where the air itself smells of toasted oak and warm vanilla. As you drive, the landscape performs quiet gestures: the flash of white-water glinting in a creek bed, a cluster of Thoroughbreds lifting their heads as you pass, a breeze carrying the cool, green scent of wild mint from the roadside. It’s the kind of trip that invites you to slow down, pull over often, and let the countryside pour itself out like a well-made drink—smooth, layered, and unmistakably Kentucky.
Getting to the Kentucky Bourbon Trail
Louisville is the most convenient entry point for most travelers, with frequent flights and easy access to the heart of bourbon country. For those coming from the north—as we did—Cincinnati provides an inviting launch point. The drive south is a leisurely one, with river valleys, farmsteads, and the first distillery rooftops rising on the horizon like old friends waiting to be rediscovered. Before you set out, download the official Kentucky Bourbon Trail app and its pocket-sized field guide. They’ll point you toward tasting rooms, help you track your distillery visits, and make it easier to secure reservations at the bigger names on the route—many of which now book up ahead. And one essential note: plan your transportation. Whether you book a guided tasting tour, hire a local driver, or appoint a willing friend as designated chauffeur, the bourbon here is meant to be enjoyed—not rushed. Take your time, sip wisely, and let the road unfold slowly.
Day 1: Covington (Northern Kentucky)
Perched along the Ohio River, Northern Kentucky has a character all its own—part river-city energy, part easy Southern charm. Covington, Newport, and Florence anchor the region with neighborhoods full of restored historic buildings, indie galleries, inventive restaurants, and just the right amount of nightlife buzz. And when you’re ready for a breath of quiet, the landscape answers quickly: sweeping overlooks from Devou Park, shady trails that trace river bends, and pockets of greenery that make you forget you’re just minutes from the city. It’s a place where bourbon tasting, gallery browsing, and scenic wandering all weave together in one effortless day.
9 a.m. — Breakfast and Private Tour at New Riff Distilling :
We began our morning at New Riff Distilling in Newport, a contemporary jewel of both the Kentucky Bourbon Trail and The B-Line. Since opening in 2014, the distillery has taken a decidedly modern approach to bourbon—respecting heritage while composing something entirely its own. A recent $3.5 million renovation has elevated the experience further: the first-floor boutique now feels sleek and curated (with the option to have bottles custom-engraved), while the third-floor Aquifer tasting lounge offers refined cocktails and panoramic views of the Cincinnati skyline from a stylish terrace. What stood out most was the distillery’s sense of identity and pride. New Riff is woman-led and LGBTQ-run, and its spirits are already finding thoughtful audiences in the UK, Ireland, Germany, and the Netherlands. Our private tour was unhurried and intimate—copper stills gleaming, oak barrels quietly working, breakfast served with just the right amount of ceremony. It felt like the kind of start that sets a tone for the entire journey: intentional, elegant, and distinctly Kentucky.
11 a.m. — MainStrasse Village
A short stroll from the riverfront, MainStrasse Village is Covington at its most charming—brick streets, 19th-century facades, and just the right amount of storybook whimsy. The neighborhood’s German heritage shows up in small, almost theatrical details: the Goose Girl Fountain at its center and the Carroll Chimes Bell Tower, where a glockenspiel performance still plays out on schedule. It feels like stepping onto the set of an old-world market town, but with a distinctly modern pulse.
MainStrasse is also one of the state’s bourbon capitals. Both Old Kentucky Bourbon Bar and Wiseguy Lounge have taken home “Best Bourbon Bar in America” honors, and they anchor The B-Line®—Northern Kentucky’s self-guided bourbon trail. This region serves as the official northern gateway to the Kentucky Bourbon Trail at large: seven distilleries, nine bourbon-forward bars (each pouring more than 100 varieties), and ten restaurants stocking deep bourbon lists and bourbon-laced dishes. It’s where the state’s bourbon culture feels both rooted and refreshingly alive.
4 p.m. — The Madison District
Downtown Covington unfolds along Madison Avenue, leading all the way to the Cathedral Basilica of the Assumption—a soaring landmark inspired by Notre Dame, with luminous stained-glass windows crafted in Munich. It’s worth stepping inside for a moment of quiet awe before diving back into the neighborhood’s energy.
The Madison District is where Covington’s dining and bar scene really comes alive. Wunderbar is a relaxed local hangout known for its giant pretzels, German comfort plates, and rotating craft beers. Three celebrated stops on The B-Line® are clustered nearby: Rich’s Proper with its New Orleans–leaning cocktails, Libby’s Southern Comfort for fried chicken worth traveling for, and The Globe, a polished bourbon bar pouring more than 100 varieties (don’t miss the bourbon slush). Just around the corner, Olla Cov turns out excellent tacos and birria alongside bright, citrusy margaritas—a perfect midday pause before the next pour. And don’t miss Revival Vintage Bottle Shop & Bourbon Bar—part museum, part dream bar, and entirely devoted to rare and vintage Kentucky bourbon. The tasting flights here feel like a time capsule in a glass.
Where to Stay: Hotel Covington
Hotel Covington has a backstory with flare: the building began as Kentucky’s first modern department store, funded by a fateful bet on a racehorse named Knowledge. Today, that historic structure has been reimagined as a boutique hotel with 114 rooms, styled with warm wood, soft textiles, and just the right amount of vintage glamour. The hotel’s gathering spaces are a highlight—an inviting courtyard, low-lit lounges, and Coppin’s Restaurant and Knowledge Bar, both celebrated stops on The B-Line® and recognized among the “Best Bourbon Bars in America.” Expect over 100 bourbons behind the bar, thoughtful cocktails, and a quietly elegant atmosphere that feels distinctly Northern Kentucky. A stay here doesn’t just give you a room—it places you in the living history of the city, with style.
Day 2: Lexington
Lexington, often called the Horse Capital of the World, blends deep-rooted tradition with effortless charm. Its equestrian legacy is tangible—tour legendary horse farms or feel the thrill of race day at Keeneland or the Kentucky Horse Park. Downtown has a lively, modern rhythm, with boutique shops, chef-driven restaurants, and intimate music and arts venues. Beyond the city, the landscape softens into rolling hills and quiet trails, inviting hikes, paddling trips, and horseback rides through picture-perfect bluegrass country.
9 a.m. — Spendthrift Farm
Spendthrift Farm offers a deep, firsthand look at Kentucky’s Thoroughbred heritage. Spread across more than 1,200 acres, the farm is home to some of racing’s most celebrated names, including Kentucky Derby champion Authentic, leading sire Into Mischief, and champions Vino Rosso, Mitole, Beholder, and Monomoy Girl, among others. The recently opened B. Wayne Hughes Visitor Center honors the legacy of Spendthrift’s late owner, whose vision shaped both the farm and its place in the sport. Today, the center serves as the starting point for tours that allow guests to explore the grounds, learn about the breeding world, and meet the stars of the stable up close. It’s an experience that blends history, horsemanship, and the quiet prestige of a farm that continues to shape the future of racing.
12:15 p.m. — Lunch at Carson’s
For lunch, head to Carson’s, a downtown favorite that blends “old Kentucky elegance” with a lively, modern spirit. Owned by Mark and Jayme Fichtner, the restaurant quickly became a local staple after opening in 2018—so much so that a second outpost recently opened in Lexington’s Hamburg district. Expect Kentucky-sourced ingredients, playful takes on comfort classics, and a strong lineup of local craft brews and cocktails. It’s warm, stylish, and unmistakably Lexington. Some standout dishes for us: the Carson’s Fried Chicken, Grilled Salmon Oscar, the Savory Chicken & Waffles, and the Banana Bourbon Bread Pudding to finish—decadent and absolutely worth it.
3:00 p.m. — Fresh Bourbon
Make your next stop at Fresh Bourbon, a new name with historic significance—recognized by the State of Kentucky as the first African American–owned bourbon brand to distill in the state since the era of slavery. Founded by husband-and-wife team Sean and Tia Edwards, the distillery was born out of a simple but radical idea: bourbon should be enjoyed however you like it, not dictated by purist rules. Their bourbon opens soft and slightly sweet, then deepens into subtle layers of spice and oak—approachable at first sip, rewarding as you linger. The newly opened downtown Lexington tasting room reflects the same ethos: warm, modern, and intentionally unpretentious. It’s bourbon culture, refreshed and reimagined.
8:00 p.m. — Dinner at The Manchester Hotel
Set in the Distillery District, The Manchester is Lexington’s newest boutique hotel, blending rickhouse-inspired textures with warm Bluegrass tones. After a quick wander through the lobby’s bottle shop and lounge, head upstairs to Lost Palm, the rooftop bar with tropical cocktails and breezy sunset views. For dinner, Granddam downstairs serves elevated Appalachian comfort dishes in a stylish yet inviting space. It’s the perfect end to a day steeped in bourbon country.
Where to Stay: 21c Museum Hotel
Set inside Lexington’s first skyscraper—the former Fayette National Bank Building—21c Museum Hotel blends historic grandeur with contemporary art-world edge. The high ceilings and tall windows remain, but the space now houses a two-story art gallery, playful design touches (including the brand’s signature penguins), and Lockbox, the hotel’s celebrated restaurant where you can dine inside the old bank vault. It’s a stay that feels both cultural and deeply one-of-a-kind—there’s nothing else in the city quite like it.
Day 4
8:00 a.m. — Keeneland
A National Historic Landmark, Keeneland racecourse is widely considered one of the most beautiful in the world—rolling lawns, stone terraces, and an atmosphere that feels both elegant and deeply rooted in tradition. Even outside its famed race meets in April and October, it’s worth visiting early in the morning to watch Thoroughbreds work the track at sunrise. The experience here goes beyond racing. The Track Kitchen serves hearty grits, biscuits, and coffee to jockeys, trainers, and owners—an only-in-Kentucky moment that’s wonderfully unpretentious. Keeneland is also home to the world’s most influential Thoroughbred auctions, drawing international buyers every January, September, and November to its striking Sales Pavilion. It’s not just a racecourse—it’s the beating heart of Lexington’s equine culture.
11:00 a.m. — Bespoken Distillery Tour
Co-owned by T.J. Rodgers and Derek Jeter, Bespoken Spirits stands apart in a category defined by long-held tradition. Rather than relying solely on years in a barrel, Bespoken uses a proprietary maturation process that achieves depth, character, and complexity with dramatically less wood, water, and energy. There’s no “angel’s share” here—no 20% lost to evaporation—just a remarkably precise expression of flavor. The result is whiskey that’s both thoughtful and forward-looking: layered, refined, and gentler on the planet. It’s a modern approach to bourbon-making that doesn’t replace heritage—but reimagines it for the next chapter.
1:00 p.m. — Bites of the Bluegrass Food Walking Tour
Spend the afternoon with Bites of the Bluegrass, a walking food and history tour that feels more like a lively progressive dinner party. You’ll wander through downtown Lexington with a local guide, tasting standout dishes, sipping cocktails (if you choose), hearing stories you won’t find in guidebooks, and meeting fellow travelers along the way. Expect Southern warmth and memorable flavors, with stops that may include Sawyer’s, Pies & Pints, Failte, Agave & Rye, and The Jockey Bar—a delicious progression from hometown favorites to playful, modern bites.
8:00 p.m. — Dinner at Mileta
Close out the evening at Mileta, where Executive Chef Alex Green crafts a contemporary, Italian-leaning menu built around handmade pastas, elegant small plates, and a standout raw bar. The dishes shift with the seasons and draw heavily on local ingredients, but the flavors travel widely. The beverage program is equally thoughtful—classic and inventive cocktails, a strong lineup of Kentucky bourbons and international whiskeys, Italian aperitifs, and a wine list that balances Old World depth with New World ease. The ambience is warm, refined, and quietly celebratory—the perfect final note to the day.
Day 5: Bardstown
Bardstown proudly wears its title as the Bourbon Capital of the World, pairing deep whiskey heritage with the warmth of small-town Kentucky hospitality. Its historic center is beautifully preserved—Federal-style homes, tree-lined streets, and My Old Kentucky Home State Park, which anchors the town’s past in story and song. Bourbon lovers will find no shortage of icons to explore: Heaven Hill, Maker’s Mark, and Barton 1792 all offer tours and tastings that reveal the craft behind Kentucky’s most famous spirit. Outdoors, the quiet beauty of Bernheim Arboretum and Research Forest invites long walks, scenic overlooks, and birdwatching among rolling hills. Time your visit well and you may experience one of Bardstown’s lively celebrations—most famously the Kentucky Bourbon Festival, where the town comes together in honor of the drink that shaped its identity.
10:00 a.m. — Maker’s Mark Distillery Sustainability Tour
At Maker’s Mark, bourbon heritage feels both intimate and iconic. The Samuels family recipe—carried through Prohibition and refined over generations—has become one of the world’s most recognizable expressions of Kentucky craftsmanship. The signature red wax seal remains hand-dipped even today, and guests are invited to dip their own bottles, a tactile moment that feels quietly ceremonial.
The grounds are unexpectedly exquisite. World-renowned glass artist Dale Chihuly has installed luminous works throughout the distillery campus, culminating in the breathtaking, backlit ceiling piece The Spirit of the Maker inside the rickhouse, along with the radiant Amber and New Oak Chandelier.
Your visit unfolds as a guided tasting, a walk through historic barrel houses, and a lingering sense of artistry—where bourbon, landscape, and light all feel intentionally composed. Maker’s Mark isn’t simply a tour; it’s a refined immersion into Kentucky’s tradition of hand-crafted luxury.
1:00 p.m. — Lunch and Sightseeing
The Old Talbott Tavern is more than a stop for lunch—it’s one of Bardstown’s most storied landmarks. Dating back to 1779, the tavern has hosted figures like Jesse James, Abraham Lincoln, and Daniel Boone, and was once owned by a member of the Beam family, tying it directly into Kentucky’s bourbon lineage. Order the classic Hot Brown here and stay a while to soak in the atmosphere of worn wood, historic portraits, and whispered legends. You can even spend the night in one of the inn’s rooms, each with its own history. And before you go, browse the souvenir shop for bourbon-inspired keepsakes to take home.
Post lunch, pick up a walking map at the Bardstown Welcome Center—it outlines 48 historic buildings that tell the town’s layered story. Steps away, the Old Talbott Tavern anchors the square, and beside it, the former 1819 Nelson County Jail now operates as Jailer’s Inn, a bed-and-breakfast with an irresistible sense of place and history. To round out the afternoon, visit the Oscar Getz Museum of Whiskey History, where rare artifacts and thoughtful exhibits trace bourbon’s cultural evolution—from its frontier origins to its modern renaissance.
3:00 p.m. — Preservation Distillery
Preservation Distillery is Bardstown’s first official craft bourbon producer and the only distillery in the area still working with a traditional pot still, focusing on very small-batch, one-of-a-kind releases. Housed in a restored tobacco barn on a historic Kentucky farm, it produces deeply flavorful bourbon drawn from a limestone-rich water source that runs 200 feet below the property. The setting feels authentic and quietly rural—an experience rooted in the land itself. Tours run daily.
4:30 p.m. — Parlour Room
We spent the afternoon in The Parlor Room for a private tasting hosted by Whitney Rye, the voice behind the Mashbill podcast—one of those experiences that feels both quietly exclusive and deeply personal.
Set in the heart of Bardstown, The Parlor Room is intimate and low-lit, with velvet textures, candlelight warmth, and that effortless Southern hospitality that makes you want to stay longer than planned. It’s a small space with big character, known for hosting live music, cultural gatherings, and conversational evenings that unfold slowly. Tasting bourbon here feels less like a tour stop and more like being welcomed into someone’s beautifully curated living room—refined, relaxed, and entirely Bardstown.
6:30 p.m. — Dinner: Toogie’s Table
Toogie’s Table brings a modern polish to classic Southern cooking, with a menu rooted in local ingredients and Bardstown hospitality. The dining room blends contemporary comfort with warm, regional character—easygoing enough for locals, stylish enough for travelers. Expect elevated takes on staples like Fried Green Tomatoes, Braised Brisket, and Shrimp & Grits, alongside cozy sides such as Smoked Gouda Mac & Cheese. Upstairs, the Bar at Toogie’s offers a relaxed space for bourbon flights, thoughtful cocktails, and small plates. It’s the kind of place where dinner lingers, conversation stretches, and everything feels authentically Kentucky—refined, welcoming, and quietly memorable. Menus change with the season, so check the restaurant’s website for the latest offerings.
Where to Stay: The Homestead at Log Still Distillery
For a stay that feels both refined and rooted in Kentucky tradition, check into The Homestead at Log Still Distillery. This historic five-bedroom farmhouse has been reimagined as a luxury bed and breakfast overlooking a serene 12-acre lake, with the distillery and the rest of the campus just a short stroll away. Each room is individually designed with a blend of heirloom charm and modern comfort.
Guests can make a leisurely day of the property: join a guided tasting at Log Still Distillery, attend an open-air concert at The Amp, or simply wander the walking paths that circle the lake, where the pace slows and the landscape does most of the talking. The Homestead feels personal, peaceful, and warmly connected to the community around it—like being welcomed back to a home you’ve always known.
Day 6: Louisville
8:30 a.m. — My Old Kentucky Home State Park
Perhaps the most storied residence in Bardstown, My Old Kentucky Home is a landmark of 19th-century America. The Federal-style mansion, completed in 1818 for John Rowan Sr., later inspired Stephen Foster’s beloved ballad “My Old Kentucky Home, Good-Night!” and remains a centerpiece of the region’s cultural memory. Guided tours lead you through more than 200 years of history—duels and horse racing triumphs, family fortunes gained and lost, and rooms filled with original antiques and remarkably preserved architectural detail. For something truly memorable, reserve the culinary biscuit experience in the restored carriage house. A guide, dressed in period attire, demonstrates the art of making traditional beaten biscuits before teaching your group how to assemble the perfect Southern ham biscuit using smokehouse-cured ham.
11:00 a.m. — Bernheim Arboretum & Research Forest
Before heading on to Louisville, take a scenic detour through Bernheim Arboretum & Research Forest, Kentucky’s official state arboretum and a 16,000-acre sanctuary of rolling meadows, quiet lakes, and deep forest trails. The visitor center—a light-filled, sustainably built space—introduces the landscape, but the real magic begins outdoors. Here you’ll find Thomas Dambo’s Forest Giants, towering wooden sculptures tucked among trees, along with a canopy walk, scent and sound installations, and pathways designed to slow your pace and heighten your senses. It’s a serene reset before returning to the road.
3.00 p.m. — Arrive at Louisville
For bourbon travelers, Louisville is where the journey gathers momentum. The city wears its spirit on its sleeve—from barrel-stave rocking chairs at the airport to cocktail menus that read like small works of art. Louisville is the place where bourbon culture feels both rooted and very much alive.
Where To Stay
Louisville offers stays for every style: The Brown Hotel exudes classic Kentucky grandeur, while The Seelbach brings Jazz Age romance (it famously inspired The Great Gatsby). Art lovers should look to 21c Museum Hotel, and design-seekers to Hotel Genevieve or The Myriad, playful and boutique-forward. For a polished, full-service stay, Omni Louisville delivers resort-style ease. But if you’re here for bourbon above all, choose Hotel Distil on Whiskey Row—set in a restored barrel warehouse, it places you steps from tastings, cocktails, and the heart of Louisville’s bourbon scene.
Day 7
As the final stop on the bourbon journey, Louisville invites you to slow down and wander at your own pace—no set itinerary required. This is a city best experienced leisurely: pop into a tasting room when it calls to you, linger over a cocktail, follow the sound of live music down a side street. Louisville rewards curiosity.
Distilleries & Tasting Experiences
One of the joys of Louisville is how walkable the bourbon scene is. Many of the city’s most notable distilleries and blending houses are just steps apart:
- Michter’s offers an intimate look at its restored historic still—and the rare chance to fill your own bottle.
- Angel’s Envy invites guests to bottle-finish their own bourbon and take part in monthly cocktail workshops.
- Copper & Kings brings a modern, unexpected edge to the landscape with American brandy, bold copper stills, and a rooftop bar overlooking the skyline.
Exploring here feels less like checking off stops and more like moving through different expressions of the same beautiful craft.
Must-See Louisville Landmarks
Begin at Churchill Downs, home of the Kentucky Derby, where the museum captures the pageantry, history, and racing legends behind the “most exciting two minutes in sports.”
At the Frazier History Museum, you’ll find a thoughtful deep dive into Kentucky identity—including bourbon culture. It’s also where you should pick up your official Kentucky Bourbon Trail passport if you haven’t already.
Don’t miss the Louisville Slugger Museum & Factory, where the story of America’s most iconic baseball bat comes to life—and where every visitor walks away with one in hand.
Then end your day at Cave Hill Cemetery & Arboretum, a breathtakingly beautiful resting place for Kentucky legends like Muhammad Ali and Colonel Harland Sanders, set among winding paths and towering old trees.
Where to Eat & Drink
Louisville’s dining scene is sophisticated, warm, and full of personality. For a taste of the city at its most creative, book 610 Magnolia, where chef Edward Lee reimagines Southern flavors with global depth. For something more casual but still stylish, Bar Vetti serves bright, contemporary Italian dishes and excellent cocktails.
Start the morning with Heine Brothers’ Coffee, or go for fresh-baked pastries and breakfast sandwiches at Butchertown Grocery or Blue Dog Bakery & Café. At lunch, order the original Hot Brown at The Brown Hotel, or settle into the old-school charm of Jack Fry’s. For dinner, Decade offers thoughtful, seasonal plates in a laid-back setting, while Barn8 Restaurant & Bourbon Bar at Hermitage Farm pairs elegant farm-to-table dining with views of rolling horse country.
And if the day calls for one last pour, close the evening at Neat Bourbon Bar or in the storied lounge at The Seelbach—both refined, atmospheric rooms where the lighting is low, the hospitality unhurried, and the bourbon list reads like a love letter to Kentucky itself.
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A New Yorker at heart, an unapologetic anglophile, national parks explorer and former head of National Geographic publishing in India, Ritika is the Global Editor for Travel and Food Network and leads all journalism across platforms, including news, digital, videos, and social media. She writes features focused on narrative storytelling, industry trends, destinations, culinary travel, and how-to advice and is an advocate for sustainable travel. You can follow her on Instagram @newyorkeratheart
