I went to Kentucky for the bourbon but came back impressed with the cycling. I mean blown away.
I’ve taken cycling vacations all over the world, from classics like Tuscany and Burgundy to hotspots like Mallorca and lesser-visited destinations like Japan, but some things about cycling in Kentucky stood out above any other place I’ve been.
Upon arrival, one of the tour guides for active travel specialist Backroads told me that while he had managed trips for the company throughout Europe and the American West, and driven alone in Asia and South America and pretty much everywhere else, he had never seen drivers as polite as in Kentucky. That didn’t make any sense to me, so naturally I thought it was marketing hype and didn’t believe it.
I was wrong. Where I live in Vermont the drivers are usually very good with cyclists and in Spain and Italy where cycling is a national sport the drivers are even better, very cyclist accustomed and patient when it comes to overtaking. But Kentucky is next level in terms of politeness, and on a windy country road you can look back to see three or four cars stacked on top of each other and trudging along, waiting until there’s a long straight and then pulling by with plenty of room . Everyone waves you through intersections and politely yields to let you in as you turn, and in 5 days and over 200 miles I have not experienced a single rude driver, comment or gesture, or even once let a car come, which I feel is too close. If you ride a bike, you know it’s just remarkable. I can confidently say that the drivers in the Kentucky Bourbon Country are some of the most polite I have seen anywhere in the world.
But that’s just the tip of the big cycling iceberg. While motorists are polite, they are also rare – I drove 21 miles on day one before seeing the second car on my route. Bourbon Country is rural but also horse country, the heart of American Thoroughbred racing and breeding. The view is always mesmerizing, past thoroughbred farms on tree-lined empty roads with perfect fences and bluegrass, endless breathtaking views, all with almost no traffic. The roads are well-maintained, and there’s plenty of hilly elevation change, giving you a significant amount of altitude training each day, plus the thrill of descents, but all without the lengthy, grueling climbs that you’ll find pretty much everywhere else that isn’t flat. In short, the riding is outstanding and it would be great even without the bourbon. But there is also bourbon.
Aside from Scotland, there is probably no place in the world more synonymous with whiskey than Kentucky. Bourbon can be legally made anywhere in the United States, but 95% of the world’s supply is made right here in the Bluegrass State, along with even more non-bourbon Kentucky whiskeys. There are more bourbon casks in the state than residents, and many of them are housed in welcoming distilleries with great tours and excellent visitor facilities.
To make the journey even more user-friendly, in 1999 the Kentucky Distillers’ Association partnered with some of the most famous names in distilling—think Maker’s Mark, Evan Williams, Jim Beam, and Wild Turkey of the Kentucky Bourbon Trail, among many others. Most tourists explore the trail by car, but since it opened and has grown in popularity, more distilleries and more route options have been added to the trail, and the Kentucky Distillers’ Association has mapped driving directions for three official “self-carrying” bicycles and publishes tours on it the Bourbon Trail, 1-3 days, total 55-188 miles and visiting 3-10 distilleries. The Kentucky Bourbon Trail website has partnered with active map specialists RideWithGPS to offer both printable maps and cue sheets, as well as turn-by-turn GPS driving directions with the app on your smartphone. All distilleries listed along the trail offer public tours and tastings.
However, this isn’t a trip I would personally recommend, with the exception of the one-day horseback ride – but that’s not long enough to experience the fascinating region. Once you go overnight, you have to carry a lot of gear, which makes it a lot more cumbersome. There are very few bike hire shops in the region and if you can find one it doesn’t have any racks or panniers which you would want meaning you basically have to drive here and bring your bike with you. Even if you do, you still have a lot of weight to lug around and can never be sure when you arrive at a distillery whether a tour is available as they are very popular and sell out, or the next one may only take hours. When a thunderstorm or other storm breaks out, you are alone and unlucky, and in general you have to do everything yourself and rely on the same public tourist offers that all motorists seek.
Every time I go on a cycling holiday, I go with a reputable tour operator who provides expert guides and van assistance during the ride for mechanical or weather-related issues (or if you just get tired). But they also pre-booked the hotels, pre-booked restaurant reservations, they transport your luggage from hotel to hotel, and add VIP extras like private tours and experiences. You’ll know what you’ll see and what special activities you’ll experience before you even drive the first mile, so you don’t have to worry about missing out.
There are several top-notch active travel specialists running organized bike tours, particularly in famous places like Tuscany, and I’ve written about many of them here on Forbes. But there are very few opportunities for the Kentucky Bourbon Trail and Backroads was the first top tour operator to take advantage of this unique opportunity and is by far the most experienced after several years. Backroads is also the oldest and largest active tour operator in the country, and one of the most luxurious. They offer preloaded GPS bike computers with turn-by-turn instructions and have a fleet of custom European titanium bikes and custom e-bikes with professional upgrades like Di2 electric shifting on road bikes. Having traveled with Backroads before, I knew the high quality to expect and was not disappointed.
The 5-day Kentucky Bourbon Trail bike tour begins in Louisville, a great city with several urban distillery experiences and great hotels, as well as the Louisville Slugger Museum, the Muhammad Ali Center and the world-famous Churchill Downs racetrack, home of the Kentucky Derby. You can come a day or two early and enjoy some of these attractions. I did just that, staying at the cool new Hotel Distil, a member of Marriott’s Autograph Collection, a brand that groups independent boutique hotels too unique to fit into more cookie-cutter labels like Westin or Sheraton. Occupying a historic building on Louisville’s Whiskey Row, the beating heart of downtown, The Distil is just steps from several top distilleries offering tours and has its own notable restaurant, Repeal Oak Fired Steakhouse. I’ve written extensively about top steakhouses around the world, but Repeal is the only one I’ve heard of that cooks with staves of whiskey barrels burning over a blazing fire, and while it sounds like a gimmick, the steaks were delicious and uniquely encrusted. I would like to eat there again tomorrow.
The 5-day journey is from Louisville to Lexington, the heart of Kentucky’s thoroughbred and whiskey culture and home of the state’s other world-renowned racetrack, Keeneland, home of the 2022 Breeders Cup. I’ve never been and stayed an extra day, to race and the trail is great one of the best and most classic around so between the two trails and all the horse related stuff along the way you can check this out like the Kentucky Bourbon and Thoroughbred Trail a cultural immersion” two for the price of one”.
The hotels Backroads uses are notable, from the historic Shaker Village to the bohemian but awe-inspiring Kentucky Castle, a bluegrass nod to Versailles, while the highlight is the final two nights at Louisville’s top luxury property, the 21c Museum Hotel. All breakfasts, lunches, and dinners along the way are included (which is not common on this type of trip), as are a couple of private distillery tours, big and small, a bourbon tasting, and several special behind-the-scenes activities, including a one insightful private tour of a world-class thoroughbred stud farm, a visit to the fascinating Kentucky Horse Park, home of the International Museum of the Horse, and even a private live bluegrass music performance. There is an optional opportunity to blend and bottle your own craft whiskey. The trip has been so popular in recent years that it has grown and grown, and next year there are 21 scheduled departures from April to October 2023. Yet despite its popularity, Backroads customer reviews have never given it anything but a perfect 5-star given rating.
The cycling in the area is just fantastic, it’s a magnet for whiskey enthusiasts, horse lovers and anyone interested in learning about the culture of the area and I can’t recommend it enough whether you’re tackling it solo or go the more leisurely route with experienced tour guides. Luxury accommodation, private tours and all the travel assistance you could ask for. It’s not the most famous bike tour in the world, but it’s one of the most entertaining. To plan or extend your trip before or after, the State of Kentucky Tourism, Louisville Tourism, and Lexington Tourism travel sites are excellent.