Lexington Historic Downtown Walking Tours

Discover why Lexington, Kentucky is known as the Horse Capital of the World on this 3.5-hour narrated tour with transportation provided on a comfortable 14-person passenger van. The tour is not all on the van, though, as destination stops are made at world famous Keeneland Race Course* and one or more of the beautiful Thoroughbred horse farms that combine to make the Lexington region the true epicenter of Thoroughbred breeding in the United States ... and beyond. All tours are given by very experienced local guides who share a wealth of stories about the history of the local area, farms, bourbon production and the Thoroughbred horse -- the world's most desired breed for winning the world's most prestigious races. * NOTE: All tour itineraries can vary/change depending on changing destination and farm availability on the specific day of the tour. This is true for all of the venues (including Keeneland at its discretion) and the Thoroughbred horse farms. Thank you for touring with us

Learn about downtown Lexington's captivating history as we take a culinary cruise to five delicious stops all in one afternoon! Discover award-winning eateries, unique foodie items like the buzz button, freshly baked breads from family-owned shops, fresh Kentucky-farmed vegetables, and more! In between bites, learn about colorful characters from Lexington's history and pass through landmarks like Skuller's Clock, The Square, and Phoenix Park.

Discover the thrilling events behind the “shot heard ‘round the world” with this self-guided driving/walking tour through Lexington and Concord. Follow the path of the very first battle of the American Revolutionary War, from a shootout in the town square to a life-or-death struggle on a narrow bridge. Step back in time and witness the courage and ferocity of the minute men who took on the greatest military power in the world. Purchase one tour per car, not per person. Everyone listens together! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months. This isn't an entrance ticket. Check opening hours before your visit.

2025: 250th Anniversary Celebration of America's Birthday! Great Boston Tours offers America's most comprehensive tour of the sites in Lexington and Concord on April 19, 1775 that triggered the American Revolution. This 250th America's Birthday tour invites history lovers on a deep dive into the beginning stages of the American Revolution. Operated by a local American history expert, the day tour offers a level of information and attention to detail that simply cannot be experienced anywhere else in the Boston area. In 2025, to celebrate America 250, our nation's birthday, the National Park Service has embarked on a massive restoration and updating of key sites, exhibits and Battle Road. New for 2025 is admission to the Concord Museum. Get ready for a once in a lifetime experience! With stops in Lexington, Concord, the Concord Museum and more, you'll experience the key moments of the events that changed the world forever.

Fresh Bourbon is the offering the newest, most unique Bourbon Tasting currently in Kentucky. We guide our guests through a full sensory tasting with food & aroma pairing, to help them explore and understand the complexities of Bourbon. You'll get hands on training from a professional local mixologists and build your own custom Old-Fashioned. Plus, historical tips, tricks and stories from the Bourbon world and an opportunity to explore more flavors through our seasonal craft cocktail menu. All of which are included in a dynamic tasting experience, in fact, the first Bourbon Tasting Experience in downtown Lexington, Kentucky!

This is Lexington's ONLY Art Tour where you can enjoy the lively and vibrant local culture by connecting with the local eclectic arts scene. Fun and well-informed guides will lead you on a tour through the downtown district, introducing you to some of our many murals, public artworks and sculptures along the way while pointing out historic buildings and sharing entertaining stories that will keep you engaged. You will check out several galleries and exhibitions with a brief overview of work on display before ending this leisurely walk at Artists’ Attic – a 22 artists’ studio cooperative – where drinks and refreshments will be waiting. Here you will be able to watch artists at work and chat with them about their creative process.

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!

Guides in authentic colonial dress will immerse you in colonial Massachusetts, where events that occurred on the Lexington Green 250 years ago changed the course of history forever. Discover how everyday people from 1775, including Captain John Parker, Abigail Harrington, and Paul Revere, stood up for what they believed in and shaped the future of the United States. Tours will begin in front of the Visitors Center, across the street from the Lexington Battle Green, at 1875 Massachusetts Avenue in Lexington.

Discover one of America’s most fascinating first ladies! The Mary Todd Lincoln House was the family home of the wife of 16th president Abraham Lincoln. Mrs. Lincoln was sophisticated, educated, and versed in politics. On the surface, her success in the White House seemed assured. Yet, few women in American history have endured as much controversy and tragedy. Tour her childhood home to explore the full story.

Let’s Roam leads the way in app-led adventure hunts! Explore top landmarks and uncover hidden gems while tackling trivia and exciting challenges. Collaborate with your team or vie for victory, discovering new facts and making unforgettable memories. Perfect for any occasion—whether it’s a bachelorette bash, birthday celebration, corporate team building, or just a thrilling day out! Each participant selects their role in this interactive journey, where surprises await at every turn.

Discover one of America’s most fascinating first ladies! The Mary Todd Lincoln House was the family home of the wife of 16th president Abraham Lincoln. Mrs. Lincoln was sophisticated, educated, and versed in politics. On the surface, her success in the White House seemed assured. Yet, few women in American history have endured as much controversy and tragedy. Tour her childhood home to explore the full story.

Visit the real locations where the American Revolution began, while listening to hilarious yet little-known stories about our ancestors. Stand on Lexington Battle Green and listen to stories about the very first days of the war and the subsequent historical events which are still relevant to us today. Fall back in time with visits to restored houses and taverns to see how the Minutemen lived. Walk the Battle Road Trail, stage to multiple skirmishes and other "treasonous" events. Visit the Old North Bridge in Concord, where the Minutemen turned back the British Redcoats! Free time for lunch in historical Concord downtown with excellent local food options! The second half the day includes a tour of the author in Concord. Tour the Louisa May Alcott Orchard House where Little Women was written. Visit the Sleepy Hollow cemetery's famous Author's Ridge. See Walden Pond and Thoreau's Cabin!

Embark on a spirited journey through the vibrant echoes of Lexington's East End, where each step reveals layers of history, culture, and intrigue. You'll indulge in expertly mixed cocktails and plates prepared by local chefs while your knowledgeable guide weaves a tapestry of captivating tales, transporting you through time. Discover a fascinating connection between Kentucky and Japan, forged by visionary entrepreneurs. Hear the thundering hooves of black horsemen who once dominated the sport of kings on the sprawling track that once graced Downtown's East End. Unravel the mystery behind a vault laden with tear gas nestled within a local showroom, a relic of bygone days with stories waiting to be told. With each revelation, you'll find yourself drawn deeper into the captivating narrative of Lexington's East End, a place where history and mystery intertwine to create an unforgettable experience. All guests must be 21+ with proper ID.

This is a fun tour especially designed for art and foodie lovers. You will start with a visit to the unique Artists' Attic space, studio home to over 20 artists, then continue through downtown Lexington where you'll see and learn about the many arts features and landmarks as well as hear entertaining stories from your lively guide. The tour will then end in the lounge of 21c Museum Hotel with appetizers and the opportunity to buy a drink from the bar. A fun time to socialize and make new friends while surrounded by the hotel's amazing contemporary art collection and enjoying fabulous finger food.

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution. You will explore the historic towns of Cambridge, Lexington, and Concord, where the American Revolution began. This tour will bring to life the places you learned about in your history classes, and give you the chance to remember the famed moments, while also challenging the nostalgic, hackneyed stories that don’t quite capture the full reality of the revolutionary period. Whether you’re a history aficionado or someone who is curious about the war but also curious to explore the towns aside from their history, your driver guide will be perfectly able to tailor the itinerary for you, giving you plenty of time to ask questions or to walk through the towns and browse as well.