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Kentucky Whiskey Train Rides

Published: September 15, 2025

By: Adam Burns

There’s something timeless about the rhythm of a train rolling through Kentucky’s bluegrass and limestone hills, past rickhouses that breathe out sweet notes of corn, vanilla, and charred oak.

For travelers who love bourbon and the romance of railroads, whiskey train rides in Kentucky blend two signature stories of the Commonwealth into one unforgettable experience.

Whether you’re a curious sipper planning your first bourbon getaway or a seasoned enthusiast seeking a fresh angle on the Kentucky Bourbon Trail, a train excursion offers a slow, scenic, and flavor-forward way to savor the state’s most famous export.

My Old Kentucky Dinner Train

The heart of the action is in Bardstown, long known as the Bourbon Capital of the World. Here, the My Old Kentucky Dinner Train, operated by the R. J. Corman Railroad Group, is the best-known whiskey-themed rail experience in the state.

Departing from a restored depot in the historic downtown, the train’s vintage, 1940s-era stainless steel dining cars set the mood the moment you arrive. Inside, gleaming wood accents, white tablecloths, and picture windows recall an era when rail travel was the elegant way to cross America, and a well-made cocktail was part of the journey.

The signature draw for bourbon fans is the Bourbon Excursion, a two-to-three-hour ride that pairs a multicourse meal with curated Kentucky whiskeys. While specific partners and flights can vary by date, you can expect pours from beloved regional distilleries—Bardstown’s Heaven Hill, Willett, and Bardstown Bourbon Company often feature in local tastings, and the broader region’s heavy hitters like Maker’s Mark and Jim Beam are frequently celebrated.

On many departures, a brand ambassador guides guests through tasting notes and the craft behind the bottles, turning each course into a story about grain, yeast, barrel, and time.

As the countryside glides by—horse farms, rolling pasture, and stands of hardwood—you’ll nose caramel and citrus, sip spice and stone fruit, and discover how a well-prepared dish can amplify a bourbon’s sweetness or tamper its heat.

Dining is central to the experience. The kitchen prepares dishes calibrated for the rails and the flights—think seared meats with demi-glace, seasonal vegetables, and desserts that play with chocolate, pecan, or custard to echo bourbon’s hallmark flavors.

Dietary needs are typically accommodated with advance notice. Seating is reserved, service is coursed, and the pace encourages conversation and contemplation rather than rushing between tastings.

The Dinner Train also hosts themed rides throughout the year—murder mystery dinners, holiday outings, and occasional collaborations that highlight a specific distillery or cocktail style. However, the Bourbon Excursion remains the headliner for whiskey lovers.

Because the most popular dates—especially weekends and peak fall foliage—sell out quickly, advance booking is essential. Expect a 21+ policy on dedicated bourbon events, with pricing and inclusions varying by date and seating.

Bardstown’s location makes pre- or post-ride exploring easy. Within a short drive you’ll find major visitor centers and rickhouses, tasting bars, and cocktail lounges.

If you plan to extend your day, consider arriving early to tour a distillery, then cap the evening on the train; or make the rail journey your opening act before an overnight stay in town and additional tastings the following day. Bardstown’s downtown is compact and walkable, with historic inns, local restaurants, and museums that trace the town’s bourbon and frontier heritage.

While the My Old Kentucky Dinner Train is the most established whiskey-by-rail experience, it isn’t the only rail outfit in Kentucky to toast local spirits. The Bluegrass Scenic Railroad & Museum in Versailles, for instance, focuses on heritage rail excursions through Thoroughbred country and to the Kentucky River.

On select dates, they’ve hosted special tasting trains featuring regional producers. Schedules and themes change seasonally, so it’s wise to check their calendar for any bourbon- or craft-spirits-focused events when planning a trip.

Elsewhere, the Kentucky Railway Museum in New Haven offers family-friendly excursions and themed runs throughout the year and has occasionally incorporated tastings into special adult events.

To the south, the Big South Fork Scenic Railway in Stearns—better known for scenery and coal history—has offered moonshine-themed outings on select dates.

While moonshine isn’t bourbon, it’s a kin spirit in Kentucky’s story and can add a fun twist to a broader rail-and-spirits itinerary if your travels take you that way. Because these tasting events are periodic and partners vary, always verify details directly with the operating railroad before you go.

Final Thoughts

For travelers mapping a broader Kentucky Bourbon Trail experience, whiskey train rides add an element you won’t capture by car alone: the sensation of sipping while the landscape itself unfurls around you.

As the rails trace old rights-of-way that once carried grain and barrels, you’re reminded how railroads helped build the bourbon industry.

Trains moved corn to the mash tuns, shipped finished whiskey to far-off markets, and connected small Kentucky towns to the wider world. Riding today’s heritage lines is a living link to that past, and the glass in your hand is the continuation of a craft perfected over generations.

If you’re choosing just one train-centered whiskey experience, the My Old Kentucky Dinner Train in Bardstown is the surest bet for a full-package meal, curated bourbon flight, and vintage rail ambiance. If you have extra time, keep an eye on the calendars of the Bluegrass Scenic Railroad & Museum and the Kentucky Railway Museum for special tasting departures that can round out a spirits-forward weekend.

And remember, the hallmark of Kentucky hospitality is the pace: you’re not checking boxes so much as enjoying moments—an aroma that surprises you, a pairing that clicks, a story from a conductor or brand host that gives you a new way to describe what’s in your glass.

Above all, sip responsibly. Bourbon is a spirit built for savoring, not speed, and rail travel is its perfect match in that regard. Between the clink of glassware, the cadence of the tracks, and the soft glow of the dining car, a whiskey train ride in Kentucky turns a tasting into a journey, and a journey into a memory you’ll talk about long after the last drop.