Kentucky’s become one of my favourite states, and I think it’s got it all for any Dad looking for fun guy adventures – and if you need to schlep the kids, there’s lots for them too. Just to name a few: the Corvette museum, horse farms, luscious food, Louisville Slugger museum, and the world’s longest cave system.

By The Numbers

Latest numbers show that the tourists are returning: trips to the state reached a whopping 70.5 million in 2021, 96% of pre-Covid levels. (To put it in perspective, 41 million visited Louisiana, and 67 million for Illinois!)

The city pulls in visitors from around the world for the annual Kentucky Derby, the most famous horserace in the US, held every May. Plus, the state’s signature culinary favorites, popular among visitors and locals, include bourbon balls (chocolate donut holes dipped in bourbon), hot browns (the famous open-face sandwich; skillet-warmed flatbread layered with fried meat, tomatoes, barbecue sauce, bologna, and turkey slices), Bergoo (meat stew with cabbage, potatoes, lima beans, corn, okra and tomatoes) and of course, Derby Pie (chocolate and walnut). How can you resist?

Where to Start

Fly into Cincinnati, and you’re a fifteen minute drive to Covington or Newport, Kentucky – a great way to start your trip.

The author, Dave Gordon, in Kentucky

Newport is famous for being the “Vegas,” before there was actually a Vegas.

The town has an edgy, storied past as a Prohibition-era bootlegging capital, a mobster’s paradise, and America’s first major gambling city. That history and the region’s Prohibition “side hustle” of bootlegging helped preserve time-honored distilling traditions for future generations of bourbon makers.

Meet your Newport Gangster Tour guide, and learn of the incredible history behind The Syndicate – the onetime “it” venue for all the big acts of the day, that is now a wedding venue. A giant mural in the lobby shows off photos of the heydey of headliner acts that came to perform there, including Frank Sinatra, Sammy Davis Jr., Bob Hope, Judy Garland, Tony Bennett, Dean Martin and so many others.

In the Streets

Stroll the streets of Newport, as you learn the jaw-dropping stories, including where mobster shootings took place (some building bullet holes remain!), who framed who, and who back-stabbed who! Famed strongmen Meyer Lansky and Bugsy Segal flexed their muscle and influence on the neighbourhood before they and others laid their footprints in the Vegas sand.

Newport on the Levee is an entertainment complex that sits on the banks of the Ohio River, and boasts some of the best skyline views of Cincinnati, and local food vendors. The indoor artisan market includes Colonel De Spices, a family business that offers over 500 culinary herbs, spices and custom blends, including mixes you can’t find anywhere else.

Of course, bourbon is a Kentucky tradition. In fact, 95% of the world’s bourbon is distilled in Kentucky, and production continues to grow. Virtually every restaurant has a bourbon menu.

Enjoy a specialty tasting in Covington, at Revival Vintage Spirits, where you can sample from among hundreds of rare and priceless 50+ year old bourbons. As America’s foremost vintage spirits collector, charismatic owner Dusty Bonds has a vast knowledge of all things boutique bourbon. Don’t be afraid to pick his brain on any given shelf item.

Head on to Louisville, the state’s largest city.

Downtown Louisville at night

Explore the relatively-new NuLu area, best known for its art galleries, growing number of ethnic restaurants, and boutique shops.

One example of the latter is Clayton & Crume, an upmarket leather goods outlet, featuring a wide array of belts, hats, wallets and coasters. Upping the swagger factor, in June they started serving cocktails in their new bar.

The place is made all the more famous because once upon a time, Muhammad Ali used to train in the building. On the second floor, a blow up photo of the famed boxer overlooks the workshop, where cow hide is splayed out on tables, ready to be cut and designed.

Food and Drink Tips

(Right around the corner grab a lunch at Royals Hot Chicken, a casual restaurant which features Nashville-style hot chicken, Southern sides and boozy milkshakes.)

And to round it out, take in the Evan Williams Bourbon Experience in downtown. Like with any bourbon tour, you’ll have an opportunity to taste a variety of types, see the machinery and barrels up close, and view a re-enactment video of how the company began almost 250 years ago.

Meanwhile, about an hour and a quarter away, the Lexington Distillery District is a recent development: a 25-acre property with distilleries, breweries, shops, restaurants, entertainment and nightlife in beautiful historic buildings. Among them, check out Ethereal Brewing for micro-brewed specialities. Then go for ice cream at Crank & Boom (with signature flavours like bourbon & honey, blackberry & buttermilk, blueberry lime cheesecake, and a dozen more!). People magazine rated it one of the top ten ice cream shops in the US. Touted as the “best date spot in Lexington,” Lockbox is inside the 21c Museum Hotel.

Whether it’s breads and spreads, shellfish, fresh spins on salads, quail, steak, scallops, fish, or the creative desserts, it’s as much a meal as an experience.

About an hour away from Lexington, is the highly-recommended Bardstown Bourbon Company tour. Start with the obligatory flight tasting, and walk right into the distillery itself, where you’re face to face with the boiling corn juice that will grow up to be fine tasting bourbon. It’s amazing to see the hundreds of thousands of barrels stacked on top of each other, and your guide will share amazing stories about how bourbon is created.

This itinerary alone could be at least four days – and there’s still so much more to tour! So if you’re thinking of that long-awaited post-pandemic trip, Kentucky’s got a great combination of fun and warm weather.


Covington: Hotel Covington, located at the Cincinnati waterfront, oozes vintage style and comfort. Rated 13th out of the 25 best hotels in America, by Trip Advistor in 2021. 15 minutes by car from Cincinnati/Northern Kentucky International Airport.

Downtown Louisville: Hotel Distil, Autograph Collection is just blocks away from the Evan Williams tour, Louisville Slugger museum, and many of the city’s finest dining establishments. It touts itself as “setting the standard for luxury in Louisville hospitality.” It earned the 2021 Trip Advisor Travelers Choice Hotel.

Lexington: 21c Museum Hotel has a bon vivant, chic boutique feel to it. The halls and public areas also double as a modern art museum and cultural center. Inside the rooms are custom-designed contemporary furnishings – a stand-out feature.


  • Louder Than Life rock music festival is set for Sept. 22-25, 2022 in Louisville.
  • Breeder’s Cup World Championships return to Keeneland in Lexington, Nov. 4-5, 2022
  • In Apr. 2022, the original KFC Sanders Cafe and Museum reopened after renovations! See the first restaurant as it appeared in the 1940s!
A race at Keeneland
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Written by Dave Gordon

Dave Gordon is a freelance writer and editor, whose work has appeared in more than a hundred publications worldwide. He has three daughters – aged 14, 12 and 10 – and has learned more about unicorns, hair braids, Little Ponies, princesses, Barbies and Fuller House than he would have ever imagined.

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