For the 50+ Traveler
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Bourbon and horses are the forces driving Lexington, Kentucky’s popularity, but tradition, class, and growth make it a place visitors will want to come back time and time again. I first visited Lexington 33 years ago, and it was nice to go back and see what had changed over the past 15 years since my last visit. Everything and nothing is my answer. I could still find the vital parts of town just like it was yesterday, with the addition of only one new mega-complex. While other cities have grown out into their suburbs and popular neighborhoods in most metropolises have changed, Lexington seems quite happy in its roots.

The Horse Capital of the World still prides itself on being a laid-back, upscale town with legendary horse racing, the Kentucky Wildcats, delicious Southern food, and a rich history, but it steps into the present with exciting new one-stop-shop complexes for shopping, dining, and entertainment, and an emerging arts scene. Here is how to spend an incredible weekend in beautiful Lexington, Kentucky.

Note: Visit Lexington paid for some of my meals and attraction tickets on my visit. As always, my opinions and reviews are 100 percent mine and are unbiased.

Things To Do In Lexington

Lexington has lots to keep you busy, from world-class horse parks and race tracks to trendy shopping areas and a famous historical plantation and home.

The Kentucky Horse Park in Lexington, Kentucky.
Melody Pittman

Kentucky Horse Park

The Kentucky Horse Park is the almighty attraction in Lexington. A venue with award-winning horses, educational talks, museums, the Big Barn, and the Hall of Champions all make visiting the park and pristine grounds a fantastic way to spend the day. Even for a horse “liker” (I’m not in love with horses as some are), I found the Kentucky Horse Park so enjoyable that I stayed for over four hours. I left feeling warm and fuzzy, having admired the beautiful creatures and learned about their racetrack lives.

Kaiser, a Clydesdale draft horse, has won more awards than all the others put together. Be sure to see him and his friend, Elvis, in the Big Barn.

My best tip for you is to arrive at the Kentucky Horse Park early and to try to do as many things on the daily schedule as you can. Activities include talks, feedings, and more. And keep your receipt in case you want to come back the next day free of charge.

The Henry Clay Estate in Lexington, Kentucky.

Ashland: The Henry Clay Estate

Henry Clay was a successful lawyer and politician who also ran unsuccessfully for president three times. Still, his role as Speaker of the House established some long-living procedures for the job. Henry Clay, also known as “Great Compromiser,” was a powerful man. He built his famed Ashland, a 19th-century estate, off the sweat of his slaves’ backs, which makes their story equally as powerful.

Ashland has three tours: the Signature Henry Clay mansion tour; Traces: Slavery at Ashland, an indoor/outdoor; and a private tour for up to six participants, which focuses on both the Signature and Traces tour topics, plus women’s voices and the grounds. I urge you to do them all; there is enough history (gambling, horse-racing, and hemp, to mention a few) and opulence to keep you interested.

The Summit at Fritz Farm in Lexington, Kentucky.
Melody Pittman

The Summit At Fritz Farm

One of Lexington’s newer attractions is the one-stop-shop I mentioned earlier. The Summit at Fritz Farm features 60 high-end retailers, including Pottery Barn, Williams Sonoma, Draper James (Reese Witherspoon’s shop), and Vineyard Vines. There is also an enormous Whole Foods Market, around 20 dining options, and even a stylish Origin Hotel. The outdoor space is visitor friendly and offers many free parking spaces, pretty seating areas, flower beds, and murals.

The Lincoln mural in Lexington, Kentucky.
Melody Pittman

Lexington Murals

Art is plentiful around Lexington, and you’ll love seeing the vibrant murals, often several stories high, in plain sight -- and the most random places. A few pieces I enjoyed seeing were Louis (Armstrong), Lily and the Silly Monkeys, and Hive Salon. You must see Lincoln (Abraham) by Kobra on the back wall of the Kentucky Theatre (or Vine Street).

The Keeneland horse racing track in Lexington, Kentucky.

Keeneland

At its finest at beautiful Keeneland, Lexington horse racing is accessible to the public in October and April. The fall meet runs October 2 through 24, and during this time, you can watch live thoroughbred horse-racing and place your bets on the winners. It’s also fun to get dressed up and have an excuse to wear a big fancy hat. I did this once and got to meet Pat Day, one of the most winning jockeys in the business, by luck. Keeneland hosts the Breeders’ Cup, too.

Lexington Green, an indoor shopping mall in Kentucky.

Lexington Green

This oldie-but-goodie mall still has noteworthy stores in it, especially Logan’s, the ultimate in men’s clothing since 1964. Lexington Green is an indoor shopping mall with an outdoor lifestyle center.

I go there for Joseph-Beth Booksellers, a two-story mammoth store with a delicious restaurant, several gift areas, and a whole floor dedicated to children’s books, toys, and fun. Bibliophiles will be in heaven and should be prepared to spend a few hours browsing the incredible selection.

North Lime Coffee and Donuts in Lexington.
Melody Pittman

Best Restaurants In Lexington

If you are a foodie or just appreciate delicious, high-quality food and chef-inspired creativity, you will be delighted by Lexington’s food choices.

Breakfast

Nate’s Coffee is a popular place to enjoy great fresh-roasted coffee, pastry, and maybe a slice of quiche. If you are staying downtown, there is one at Cheapside Park with outdoor seating that’s great for people watching and a view of the Historic Lexington Courthouse. You could also venture over to North Lime Coffee and Donuts for insanely good donuts, some even square shaped.

Or, if you want a big breakfast, Wild Eggs is a bright and cheery eatery with some tasty items, like Strawberry Tallcakes and chicken and waffles. If you aren’t counting calories, my favorite menu item is the Mr. Potato Head Casserole, with cheese, breakfast sausage, tomatoes, poblanos, mushrooms, and onions, all drenched with queso and topped with an egg however you like it. Wear your stretchy pants, but walk away really happy.

Food from Red State BBQ in Lexington.

Lunch

My favorite Lexington lunch is Red State BBQ, in an unassuming shop on the outskirts of town, and with fewer crowds than downtown. Go for the down-home food like pulled pork, sliced brisket, or ribs, and choose from a smorgasbord of side items. Red State’s baked beans, corn casserole, and coleslaw are highly popular. Try all of the barbecue sauces; they are tasty!

A second choice is Pies and Pints, with specialty pizza creations and some ingredient combinations that may shock you. The Steak and Mushroom (with horseradish crema) is my favorite, but the Grape and Gorgonzola (with rosemary) is a close runner-up. Pies and Pints allows you to half two gourmet pizza types into one pizza, so you don’t have to eat the same thing as your companion. Pies and Pints is at The Square, formerly known as Victorian Square, downtown.

The writer's meal from Honeywood in Lexington.
Melody Pittman

Dinner

Oh baby, now we’re talking! My favorite place to eat in Lexington (which I discovered during my recent trip) is Honeywood in The Summit at Fritz Farms. This chic eatery boasts indoor/outdoor seating, a James Beard-nominated chef, killer cocktails, and over-the-top good food. I ordered the veggie plate, my choice of three side items (Weisenberger cheese grits -- a must -- plus greens, and creamed spinach with mushrooms), and paired it with a hoecake, which is like a cornbread pancake. Every bite was fantastic, but the best came last ... chocolate banana pudding as you’ve never had it. Life-changing.

If you are at the bookstore for hours like I predict you may be, their restaurant, Bronte Bistro (opens as PDF), has great selections, too. Kentucky is known for its legendary Hot Brown, and you can find it on the menu there. A Hot Brown is turkey (and ham, too, in this case) over toast with tomato and bacon slices, and a mornay sauce. It is rich and filling, and a must when you visit the Bluegrass State.

Where To Shop In Lexington

Besides The Summit at Fritz Farms, Lexington has popular shopping at Fayette Mall, a regional shopping mall and the largest in Kentucky. There are over 170 stores, along with anchor stores Macy’s and Dillards.

You’ll find plenty of boutiques around the Lansdowne Shoppes with jewelry and women’s and children’s apparel.

Old Kentucky Chocolates is a store worth visiting for delectable candies, bourbon truffles, sea salt caramels, and chocolate-covered potato chips. It has been in business for 55+ years.

A room at the 21C Museum Hotel Lexington.
Melody Pittman

Best Hotels In Lexington

The 21C Museum Hotel Lexington is the city’s luxury hotel. Situated downtown in walking distance of many points of interest and adjacent to the beautiful courthouse, the 21C Lexington offers gorgeous rooms, an onsite restaurant (Lockbox), and a two-story art gallery.

The 21C hotel brand is one of my favorites: I love their trendy and tasty restaurants, artful interiors, contemporary furnishings, Malin+Goetz toiletries, and the rubber ducks that come with your toiletries for enjoying in the bath (or shower). Each 21C Hotel (there are almost a dozen) emphasizes art, and the nearly human-size penguins are the brand’s recognizable mascot. Lexington’s penguin is a royal blue -- go figure.

The stately Griffin Gate Marriott is another great choice for accommodations. The rooms are pretty standard, but the property is anything but. With a golf course, restaurant, coffee shop, and full-service luxury spa, you can’t go wrong with this hotel that is minutes from the interstate and has lots of space, indoors and out, to roam around freely.

You’ll find a handful of bed and breakfasts in Lexington, too. The Lyndon House downtown has attractive furnishings, free breakfast, Wi-Fi, and parking. For more inspiration, read up on:

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