I went to Kentucky for the bourbon, but came back awed by the cycling. I mean blown away.
I have done cycling trips as vacations around the world, from classics such as Tuscany and Burgundy to hotspots like Mallorca to less visited destinations such as Japan, but several things about riding in Kentucky stood out above every other place I have been.
Upon arrival, one of tour guides with active travel specialist Backroads told me that even though he had led trips for the company across Europe and the American West, and ridden on his own in Asia and South America and pretty much everywhere else, he had never seen drivers as courteous as in Kentucky. That made no sense to me, so of course, I figured it was marketing hype and did not believe him.
I was wrong. Where I live in Vermont, drivers are typically very good about interacting with cyclists, and in Spain and Italy, where cycling is a national sport, drivers are even better, very used to cyclists and patient when it comes to passing and such. But Kentucky is next level in terms of politeness, and on a windy country road you might look back to to see three or four cars stacked up and plodding along, waiting until there’s a long straightaway and then passing with tons of room. Everyone waves you through intersections and yields politely to let you in when turning, and in 5 days and over 200 miles, I did not experience a single rude driver, comment, or gesture or even once have a car come what I consider too close. If you ride a bike, you will know that’s simply remarkable. I can say with conviction that the drivers in Kentucky bourbon country are the politest I have seen in the world.
But that’s just the tip of the great cycling iceberg. While motorists are polite, they are also rare – the first day I rode 21 miles before I saw the second car on my route. Bourbon country is rural, and it is also horse country, the heart of American thoroughbred racing and breeding. The views are constantly mesmerizing, past thoroughbred farms on tree-lined empty roads with perfect fences and bluegrass, endless drop-dead views, all with almost no traffic. The roads are well maintained, and there is a lot of rolling elevation change so you get the workout of gaining significant elevation each day, plus the thrill of downhill rushes, but all without any of the prolonged grinding climbs you find pretty much everywhere else that is not flat. In short, the riding is stellar, and it would be great even without bourbon. But there is also bourbon.
With the sole exception of Scotland, there is probably no place on earth more synonymous with whiskey than Kentucky. Bourbon can legally be produced anywhere in the United States, but 95% of the world’s supply is made right here in the Bluegrass State, along with even more Kentucky whiskies that are not bourbon. There are more barrels of bourbon ageing in the state than there are residents, and many of them are at welcoming distilleries with great tours and excellent visitors’ facilities.
To make the trip even more user friendly, in 1999 the Kentucky Distillers’ Association teamed up with some of the most famous names in the distilling business – think Maker’s Mark, Evan Williams, Jim Beam, and Wild Turkey, among many others – to create the Kentucky Bourbon Trail. Most tourists explore the trail by car, but since it opened and has become increasingly popular, more distilleries and more route options have been added to the Trail, and the Kentucky Distillers’ Association mapped and published directions for three official “self-supported” bike tours of the Bourbon Trail, from 1-3 days, totaling 55-188 miles and visiting 3-10 distilleries. The Kentucky Bourbon Trail website has teamed up with active mapping specialist RideWithGPS to offer both printable maps and cue sheets as well as turn-by-turn GPS directions using the app on your smartphone. All of the distilleries listed along the way have public tours and tastings.
However, this is not a trip I would personally recommend doing self-supported, with the exception of the single day 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 far more cumbersome. There is very little in the way of bike rentals available in the region, and if you find one, it won’t have racks or panniers you’d want, which means you basically have to drive here and bring your bike. Even if you do, you still have to lug a lot of weight and can never be sure when you arrive at a distillery whether a tour will be available, as they are very popular and sell out, or the next one might not be for hours. If a thunderstorm or other bad weather breaks out, you are on the road on your own and out of luck, and in general, you have to do everything yourself and rely on the same publicly accessible tourism options all the drivers are looking for.
Every time I go on a cycling vacation, I go with a well-regarded tour operator that provides expert guides and van support during the ride for mechanical or weather-related issues (or if you just get tired). But they also have the hotels pre-booked, dining reservations pre-booked, they move your luggage from hotel to hotel, and add VIP extras such as private tours and experiences. You know before you ride the first mile what you are going to see for sure and all the special activities you will experience, and don’t have to worry about missing out on anything.
There are several topnotch active travel specialists running organized bike tours, especially in iconic places like Tuscany, and I have written about many of them here at Forbes. But there are very few options for the Kentucky Bourbon Trail, and Backroads was the first top tour operator to jump on this unique opportunity and is by far the most experienced, after doing it for several years. Backroads is also the nation’s oldest and largest active travel tour operators, and one of the most luxurious. They provide pre-loaded GPS bike computers with turn-by-turn directions and have a fleet of custom-made European titanium bikes and custom e-bikes, with professional-level upgrades like Di2 electric shifting on road bikes. I had traveled with Backroads before and knew the high-level of quality to expect, and was not disappointed.
The 5-day Kentucky Bourbon Trail Cycling trip begins in Louisville, which is a great city with several urban distillery experiences and great hotels, as well as the Louisville Slugger Museum, Muhammad Ali Center and world-famous Churchill Downs racetrack, home of the Kentucky Derby. You can come a day or two early and enjoy some of those attractions. I did just that and stayed at the cool new Hotel Distil, a member of Marriott’s Autograph Collection, a brand that groups independent boutique properties too unique to fit into more cookie cutter labels like Westin or Sheraton. The Distil is in a historic building on Louisville’s Whiskey Row, the vibrant heart of Downtown, and sits just steps from several top distilleries offering tours, and has its own remarkable eatery, Repeal Oak Fired Steakhouse. I have written extensively on top steakhouses around the world, but Repeal is the only one I have ever heard of that cooks over live fire from burning whiskey barrel staves, and while it sounds like a gimmick, the steaks were delicious and uniquely crusted. I’d gladly eat there again tomorrow.
The 5-day trip goes from Louisville to Lexington, the heart of both thoroughbred and whiskey culture in Kentucky, and home to the state’s other world-famous racetrack, Keeneland, host of the 2022 Breeders Cup. I’d never been and stayed an extra day to attend the races, and the track is great, one of the best and most classic anywhere, so between the two tracks and all the horse related stuff along the way, you can look at this as the Kentucky Bourbon and Thoroughbred Trail, a two-for-the-price-of-one cultural immersion.
The hotels Backroads uses are remarkable, from the historic Shaker Village to offbeat but impressive Kentucky Castle, a Bluegrass nod to Versailles, while the highlight is the last 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 the norm on these kinds of trips), as are a couple of private distillery tours, big and small, a bourbon tasting and several special behind the scenes activities, including an eye-opening private tour of a top thoroughbred stud farm, a visit to the fascinating Kentucky Horse Park, home to the International Museum of the Horse, and even a private live bluegrass music performance. There is the optional chance 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 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 region’s culture, and I cannot recommend it enough, whether you tackle it solo or go the cushier route with expert tour leaders, luxe lodging, private tours and all the trip support you could ask for. It’s not the most famous cycling trip in the world, but it’s one of the most fun. To help plan or extend your trip before or after, the travel sites of the State of Kentucky Tourism, Louisville Tourism and Lexington Tourism are all excellent.