Kentucky Tours

Old Louisville is home to impressive Victorian mansions that trace back to wealthy families in the 1800s. On this walking tour, uncover the eerie past of the neighborhood alongside a guide who regales you with several ghostly tales. Stop at several points of interest including the Conrad-Caldwell House Museum, the Witches' Tree, and the Filson Historical Society.

Discover the heart and soul of Kentucky’s beautiful Bluegrass horse country on this guided, 3-hour, small-group tour. Get a behind-the-scenes look at the thoroughbred horse lifestyle and learn about the history of Calumet Farm, home to a breeding and racing dynasty that dominated the Sport of Kings during the 1940s, 50s and beyond. Also, see where scenes from the movies ‘Secretariat,’ ‘Seabiscuit’ and ‘Dreamer’ were filmed.

Discover the history and heritage of the Kentucky Derby with admission to the Kentucky Derby Museum at Churchill Downs Racetrack. Explore two levels of exhibits on a self-guided tour, then take a 30-minute, guided walking tour of the Churchill Down Racetrack.

Be transported back to Louisville during the Prohibition era and learn about the city’s haunted past as you discover speakeasies, a ghost-infested hotel, and other important landmarks. Stop for local bites at four venues and enjoy prohibition-era cocktails as well as a bourbon tasting while learning about prohibition history. End with a dessert and a cocktail with a view overlooking downtown Louisville.

Kentucky is renowned for its horse programs and farms, this is your chance to see the prestigious facilities up close. Tour area horse farms—some that are usually closed to the public—to get a look at the work that goes into raising and caring for thoroughbreds. The tour includes time to meet and interact with the horses, maybe even feed them their favorite peppermint treats.

Get your bearings in Louisville and learn about two of the city’s most storied neighborhoods with this cultural and culinary stroll through the Original Highlands and Cherokee Triangle districts. Admire Victorian homes, contemporary street art, and vibrant shopping and dining scenes as you nibble and sip your way along the historic streets. Pass the final resting places of Mohammed Ali and Colonel Sanders, plus sample bourbon and local specialties.

Step back in time and discover the history of Louisville during an immersive walking tour through the historic center. Listen to stories of wealthy titans who used to roam the streets as you explore sights including St. James Court, Ormsby Avenue, Floral Terrace, and Millionaires Row. You also have the chance to admire the old Victorian architecture that dots the neighborhood.

Explore Louisville's chic NuLu District, where vibrant murals adorn historic brick buildings, and local shops showcase artisanal treasures. Our guided walking food tour unveils the tales of Louisville, NuLu, and Kentucky through the lens of food. Your tour will showcase Kentucky heritage dishes like bourbon balls and fried chicken, as well as Appalachian classics and a curious local confection inspired by a Victorian actress. In addition, you'll visit historic sites such as the Thomas Edison House while learning about the story of Louisville and exploring the historic neighborhoods of NuLu and Butchertown, immersing you in the cultural tapestry of Louisville. With six delectable stops, this culinary adventure promises a feast for your senses, celebrating the flavors and spirits of Bourbon City. Come hungry and ready to toast to Louisville's culinary legacy!

Get to know the charms of Lexington as you eat your way through the Kentucky city’s downtown on this walking food tour. You’ll learn all about the history and culture of the “Horse Capital of the World” as your guide shares insights about the landmarks you pass. The tour will make five stops and includes food ranging from traditional Kentucky specialties to modern innovations.

Travel the Trail Tours strives to have efficiently planned tours, with reserved tour times, using comfortable vehicles. Our driver/guides are all friendly and knowledgeable and will add to your enjoyment of your time in Bourbon Country.

Join us in the lively Distillery District for a journey in time you won't forget! Town Branch Creek won't be the only thing flowing as we sip on limestone filtered bourbons, sample long-standing Kentucky cuisine, and explore the stories behind this revitalized piece of Lexington's history. You'll sample cider, farm-to-table fare, German inspired bites, sophisticated cocktails, Kentucky staples like burgoo, award-winning ice cream, and the bourbon that built this 25 acre property, all while hearing well-researched history woven into a day filled with fun and new friends!

Discover the rich history and beautiful architecture of Old Louisville as you embark on a walking tour through the city. Walk past impressive Victorian homes, once owned by wealthy families from the bourbon, tobacco, and racetrack industries, and learn about their history. You also stop at several points of interest including the Witches' Tree, Conrad's Castle, the Filson Historical Society, and Central Park.

Explore Cincinnati without having to walk on this sightseeing bus tour. Enjoy a multimedia presentation with more than 1,000 historic photos and videos that show the development of the city as the bus drives around past landmarks that include Fountain Square, Paul Brown Stadium, Great American Ball Park, Findlay Market, and more.

In addition to visiting Buffalo Trace and Four Roses distilleries, the third distillery depends on availability and you can choose from Woodford Reserve, Bulleit Frontier or Stitzel Weller. Don't miss visiting these famous distilleries and learning how they work. Lunch is not included in the price, it is optional.

Embark on a journey to explore the rich flavors, history, and influence of bourbon on this unique walking food tour. Traverse the trendy NuLu neighborhood as the sun sets, discovering hidden speakeasies, rooftop terraces, renowned restaurants, and inviting tasting rooms. Each location is known for their dedication to crafting exquisite bourbon tastings and cocktails. Unlock new flavor notes as you indulge in 8-10 meticulously paired bites, 2 tastings and 3 cocktails that showcase bourbon's unexpected versatility, all while learning the fascinating and complicated history of Kentucky's beloved amber spirit. Whether you're a bourbon novice seeking a fantastic introduction or a seasoned aficionado looking for a master class in bourbon and food pairing, this tour promises an unparalleled exploration. Get ready to reimagine your perception of Kentucky bourbon and go beyond the barrel on this one-of-a-kind experience!

Uncover the sordid past and rich history of Louisville on a ghost tour through the city's old town. Walk past impressive Victorian mansions and old buildings, listening to stories about their otherworldly residents. See the Filson Historical Society, the Conrad-Caldwell House Museum, Louisville's Central Park, and the Witches' Tree.

Visit four of Louisville’s most famous bourbon distilleries--and stop for tours and tastings at two of them--with this customizable group tour. You can choose from a number of different distilleries, including the famous Bulleit Distilling Co Visitor Experience and the historic Buffalo Trace Distillery, with the option to add additional tastings to your tour on request.

Discover Historic Old Louisville's rich architectural heritage on this walking tour that showcases the nation's largest contiguous Victorian Mansion district. Follow your guide through history-rich streets as they reveal the history behind these beautiful buildings and the surrounding area, and answer any questions you may have about the history and culture of Louisville.

Maximize time in Kentucky with a full-day distillery tour. Get picked up at your hotel or the address of your choice in Louisville and skip the hassle of driving. Set out on a small-group tour to visit distilleries and learn about bourbon production. Choose from an extensive list including distilleries like Woodford Reserve, Wild Turkey, Four Roses, and more. Tours and tastings are included.

No shared buses! This is a private vehicle for you and your group. On this full-day private Bardstown KY, bourbon distillery tour, you will visit three separate distillery operations. On these stops, you'll learn information about making bourbon, while learning the history of some iconic brands. For this tour, please select (5-6) distilleries from the list ranked in order of importance. From there, we will coordinate with you and book (3) distillery tours with tastings for your group. These will booked based on availability, scheduling, and your ranking and your approval. By booking this tour, you'll receive: - Hassle-free booking - A private vehicle for your group - Free pickup from your Louisville hotel or AirBnb - Base-level admission to 3 distilleries - A knowledgable & friendly designated driver * Note, we will stop for lunch, but it is not included in this online price. Please send an email for questions. This tour will take about 8-9 hours in total.

Experience Kentucky’s history of bourbon by bypassing the jam-packed distillery tours and heading to the water during this Frankfort Bourbon Boat Tour and Tasting. Set out on the Kentucky River to hear the history of this hard alcohol in the Bluegrass State. Find out there’s much more to Kentucky bourbon than just corn and pass by the Daniel Boone Burial Site and Kentucky State Capitol.

No shared buses! This is a private vehicle for you and your group. On this full-day private Lexington, KY, bourbon distillery tour, you will visit three separate distillery operations. On these stops, you'll learn information about making bourbon, while learning the history of some iconic brands. For this tour, please select (5-6) distilleries from the list ranked in order of importance. From there, we will coordinate with you and book (2) distillery tours with tastings for your group, and (1) guided tasting only experience. These will booked based on availability, scheduling, ranking, and your final approval. By booking this tour, you'll receive: - Hassle-free booking - A private vehicle for your group - Free pickup from your hotel or Airbnb - Base-level admission to 3 distilleries - A knowledgeable & friendly designated driver * Note, we will stop for lunch, but it is not included in this online price. This tour will take about 9 hours in total.

Get a feel for life in the Bluegrass State during this small-group tour that combines a visit to three of Lexington's famed horse farms with an opportunity to shoot clay pigeons at a members-only venue, not usually open to the public. After a morning of clay target shooting, see some of the training facilities that make Kentucky such a legendary site for horse breeding and racing. Easy Lexington pickup is included.