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  • Writer's pictureJoseph Bourbon

19 Things to Do in Lexington

I’ve spent a lot of time in Lexington, KY over the years. From a quick weekend getaway to horse competitions to distillery tours, I’ve never been bored in the bluegrass state. Here are some of my favorite things to do in Lexington.

Southern Lights at the Kentucky Horse Park

If I had a dollar for every time I’ve been to the Kentucky Horse Park, I’d be a very rich man. While my older daughter has competed at an event here at least once a year since she was 10, we’ve also made many trips through the museums, watched the Parade of Breeds Show (which my daughter worked in during her college years), and walked through some chilly winter weather at the Southern Lights holiday festival. KHP is a wonderful stop for families, and anybody with an interest in the equine industry. Kentucky is known for horses and bourbon so taking a trip through this park is certainly worth it.

This is a beautiful race track and a must for anyone visiting Kentucky. While there are only races during April and October, there’s plenty to do year-round including touring the grounds, watching the morning workouts or grabbing breakfast with jockeys and trainers at the Trackside Restaurant. If you’re there during the spring or fall racing meets, you’re in for a treat. I recommend picking up a Buffalo Bow Tie cocktail, some bread pudding, and settling in to watch some horse racing.

History buffs won’t be disappointed by this quaint stop in downtown Lexington. Born in Lexington in 1818, Mary Todd lived at this 14-room home from 1832-1838, until she moved to Illinois to live with her sister Elizabeth in 1839. It was there that she engaged in local politics and met a rising young lawyer and politician named Abraham.

Woodford Reserve was the first distillery I ever toured, and holds a special place in my heart. Besides having one of the (if not the) best tours in the industry, and also sits on an absolutely beautiful piece of land. If you’ve never toured a distillery before or if you’ve seen them all, Woodford Reserve is a must stop for any trip to Lexington.

Buffalo Trace Distillery

Although you won’t get your Kentucky Bourbon Trail passport stamped at this stop, it shouldn’t be overlooked. Buffalo Trace is one of the few distilleries left in the area offering free tours. And if you take the family, the kids can try some of Freddie’s Old Fashioned Root Beer Soda (which for adults is paired with Buffalo Trace Bourbon Cream for an alcoholic-mock-root-beer-float). The distillery is technically in Frankfort, KY, but it’s only a 30 minute drive from Lexington!

Located in nearby Lawrenceburg, KY, you can check out the Four Roses Distillery. Modeled in a 1910 Spanish Mission-style construction, the quick one-hour tour will take you from grain to finished product. You will get a Kentucky Bourbon Trail stamp here, but you’ll have a 45-minute drive to see the finished barrels age at the Cox Creek Warehouses.

If you make it over to Four Roses, you might as well swing by Wild Turkey while you’re in the area since both of these distilleries are located in Lawrenceburg, KY (about 30 minutes from Lexington). The new visitors center hosts a beautiful tasting room and unique collection of old advertisements. While I haven’t run into Matthew McConaughey (brand spokesman) here, it’s certainly worth it to take a tour and enjoy some of their fine bourbon.

Lexington Brewing

This is one of the few distilleries located in Lexington, instead of one of the surrounding towns. The standard tour guides you through Lexington Brewing & Distillery – the distillery part being the producers of Town Branch bourbon. This is a unique tour because it consists of beer, bourbon, and whiskey tastings. If you’re traveling with someone who isn’t a bourbon fan, this is a great tour to go on. You get tokens to pick what you taste – so you can choose to taste only beers, only whiskies, or a combination. And if you’re traveling with close friends or family as I’ve done, you can steal a sip from their selections as well to get a wider tasting.

Castle & Key

Castle & Key is located in the previous Old Taylor Distillery (of Col E.H. Taylor fame). Just a few years ago, this facility was overgrown with greenery, stripped of its copper, and left barren. Now, it serves as a testing ground for Castle & Key bourbon, gin, and vodka. While the bourbon is still aging in barrels, the gin and vodka are available for tasting and purchase. The tour here is absolutely remarkable – full of history, beautiful gardens and springs, and a wonderful experience from start to finish. Master showman Col E.H. Taylor would be proud to see what the distillery was up to these days.

Shaker Village

This historic landmark was home to the third largest Shaker community in the United States between 1805 and 1910. Nowadays, it hosts families as they tour the facilities, stay in the restored Shaker buildings, and if you’re lucky like I’ve been – enjoy an orchestral masterpiece in the Meadow View Barn.


Carson’s is a foodie and bourbon lover’s paradise. They have one of the largest bourbon selections I’ve seen and offer a solid, reasonably-priced bourbon flight. They take a gourmet twist to the typical pub food to make for a great pairing with the bourbon. Caron’s has great bourbon, a hip atmosphere, and tasty food menu – all combine into a trifecta success in my eyes (and taste buds).

Located in nearby Midway, Kentucky, you’ll quickly feel at home here. On any given date, you’ll see a wide variety of diners – Keeneland Race Track attendees, horse farm workers, equestrians in breeches and tall boots straight from the barn, and locals enjoying a night out. The fish and chips made with Kentucky Bourbon Barrel Ale is always a favorite of mine, as are the New York style hand tossed thin crust pizzas. You can sample a local favorite – the Hot Brown – and be sure to save room for dessert. If you catch their Kentucky Derby Pie – it’s a great day!.

When looking for a hearty breakfast, my standard is Josie’s. No matter the time of day, breakfast is served and my go-to at this family cafe. I’m never disappointed when I eat here. You’ll find farm-to-table with locally sourced eggs, bacon, and fruit toppings for the pancakes and waffles. There is nothing – NOTHING – like farm fresh food and Josie’s has yet to disappoint.

I know donuts is literally in the name, but my favorite item here is more of a muffin called Cinna Monkey. That’s right – monkey bread. In a muffin. If you’re short on time, looking for something to grab and go, or just wanting a more casual vibe, look no further than North Lime.

This restaurant looks like one of the sketchiest restaurants from the outside, but inside makes the best barbeque, corn pudding, beer cheese grits, and corn muffins that I’ve ever had. They don’t waste time or money with fancy decorations, but you’re guaranteed to enjoy some great Southern cooking and the typical Southern hospitality.

Looking for fine, local cuisine – from casual to button-down and blazer? Check out any of Chef Ouita Michel’s restaurants. Join the locals at Wallace Station – featured on Guy Fieri’s “Diners, Drive-ins and Dives” – in nearby Midway. Be sure to sample a Kentucky classic Hot Brown and Lemon Bar. Or, grab a cold pint at West Sixth Brewing and stroll across the lobby to Smithtown Seafood to pair that pint with delicious fish & chips. After a day exploring, settle in for a slow dinner at Honeywood at the Summit at Fritz Farm. Enjoy an expertly crafted Old Fashioned along with slow-cooked pot roast or a Hoecake Burger.

Country Boy is something my oldest daughter recently introduced me to, and it didn’t disappoint. Located in what feels like literally the middle of nowhere, it’s full of energy and great beer. I was surprised to find great stouts (my younger daughter’s favorite beer), and lighter ales (my older daughter’s favorite) – and everything in between, all at a high quality.

Equus Run Vineyards

My wife enjoys the history of distilleries but isn’t a huge fan of the bourbon itself. So when we’re in Kentucky, we make sure to stop by her favorite winery – Equus Run. Located in Midway, it’s only 20 minutes from Lexington and in absolute paradise. The wine here is some of the best I’ve had – even for a bourbon drinker like myself. We love grabbing a bottle, sharing some cheese and crackers, and sitting out on the porch at Equus and admiring the beautiful gardens. This isn’t the largest winery in the area, but it’s certainly our favorite.

19. Drive around

Tourism costs money. There’s no way around it. However, one of my favorite activities in Kentucky is driving around and looking at the horse farms, the rolling hills, and the Kentucky bluegrass. This shouldn’t be overlooked just because it’s free.

All in all, do one or any of these and you won’t be disappointed. Lexington is one of my favorite places in the world, and I hope you can make a stop and see why it has become my second home.

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