Spending A Day In Lexington

Sabah Drabu

6 mins read

Apr 10, 2024


A Guide To Spending A Day In Lexington

Right in the belly of Kentucky, where bourbon flows like a lively river and horses kick up the charm, Lexington isn’t just a place—it’s a vibe. It’s where tradition does a tango with class, and growth throws a party.

Forget what you know about this city being all about horses and hearty home-cooked meals—Lexington is like a secret handshake you didn’t know you needed. In this guide, we’re diving headfirst into the city’s flavors, unraveling the coziest hideouts, savoring the yummiest bites, and basking in the good vibes. Let’s get ready to taste the magic and feel the love in Lexington!

Where to Stay

Choosing suitable accommodation is your first step to an unforgettable experience. From spirited atmospheres to boutique charms, Lexington’s array of hotels promises a stay and an immersion into the city’s unique character. Let’s explore the diverse options beyond mere lodgings, offering an enriching blend of comfort, history, and local flair.

The Manchester Hotel

A self-proclaimed “spirited place,” The Manchester Hotel sets the stage for an unforgettable stay. The rooms embrace modernity with a creative nod to history and are in bourbon’s rich hues. It’s a symphony of deep browns, maroons, and blues, echoing the city’s roots in the bourbon industry.

From breakfast to a nightcap, the menu unveils upscale twists on southern favorites — shrimp and grits, biscuits and gravy, deviled eggs, and mint juleps dance on the taste buds.

Ascend to the top floor, and you’ll find the Lost Palm, a 1960s-inspired rooftop oasis reminiscent of Southern Florida. Picture flamboyant cocktails, small bites, and a fresh seafood tower against the backdrop of Lexington’s skyline. The Manchester isn’t just a place to rest; it’s a sensory journey through Kentucky’s history and hospitality.

21c Museum Hotel Lexington

For art lovers, 21c Museum Hotel Lexington is a masterpiece. This boutique hotel boasts custom-designed furnishings, Nespresso coffee machines, and marble baths. The 21C Suite provides a lavish retreat with a plush king bed and floor-to-ceiling windows. It has an on-site contemporary art museum and cultural center to add a cultural dimension to your stay.

Elwood Hotel & Suites

Experience boutique charm at Elwood Hotel & Suites, celebrating the contemporary Southern lifestyle. With retro-chic touches, black-and-white photos, and vintage-inspired Galanze mini-fridges, each of the 62 unique rooms feels like a personalized haven. The Fiddletree restaurant downstairs serves Southern comfort food and handcrafted Kentucky bourbon cocktails, occasionally accompanied by live music.

D. Origin Hotel Lexington

Origin Hotel Lexington invites you to modern comfort within The Summit at Fritz Farm. Choose from 120 well-appointed rooms and suites, surrounded by over 60 shops and 20 restaurants. Enjoy thoughtful freebies like parking, Wi-Fi, and fully outfitted fitness center access. Plush beds, luxury linens, and large glass showers await in every room, ensuring a rejuvenating stay.

Lexington Marriott City Center

For those who prefer to be at the heart of downtown, Lexington Marriott City Center is a luxurious choice. Experience the city’s best shops and Southern restaurants steps away. Indulge in a seasonal rooftop pool, a state-of-the-art fitness center, and a rooftop restaurant serving locally sourced dishes and craft cocktails. The rooms have facilities for relaxation and productivity, with designated work desks, high-speed Wi-Fi, and plug-in panels for your devices.

Where to Eat

Embark on a gastronomic journey as we explore the culinary landscape of Lexington, where each bite tells a story of tradition, innovation, and Southern hospitality. Lexington’s dining scene promises a feast for the senses. Join us on this flavorful adventure through the Bluegrass state’s diverse and mouthwatering offerings.


When it comes to indulgence, Malone’s stands as a local beacon. A haven for premium cut steaks, sushi, seafood, and an awe-inspiring tower of desserts, chefs in Lexington at Malone’s cater to local palates and those seeking a culinary adventure. Imagine layers of angel food cake, black cherry ice cream, chocolate chunk ice cream, Oreo cookie crumb crust, and myriad toppings converging into a dessert tower, inviting you to save room for a sweet symphony.


Tucked within the 21C Hotel, Lockbox is not just a restaurant; it’s an art-infused culinary haven. Warm griddled banana bread, ham and sweet corn hushpuppies, and pimento mac and cheese elevate your brunch experience. As you savor each bite, rotating art exhibits unfold around you, turning your meal into a multisensory journey through Lexington’s vibrant cultural scene.

Blue Skillet

No visit to the Bluegrass state is complete without a taste of soul food, and Blue Skillet in Lexington is a culinary maestro in this realm. This place features daily specials with baked chicken, meatloaf, fried pork chops, green beans, mashed potatoes, cabbage, and greens — a true Southern feast. Don’t be deterred by a line; the wait is a prelude to an authentic Kentucky culinary experience.

Corto Lima, Belle’s Cocktail House, Crank & Boom Ice Cream Lounge

For those craving Latin-inspired delights, Belle’s Cocktail House’s rooftop bar beckons with stunning views of downtown Lexington. Meanwhile, Crank & Boom Ice Cream Lounge in the Distillery District serves up ice cream flights and sundaes inspired by Bourbon Country. Imagine indulging in a flight with flavors like Honey & Bourbon, a testament to Lexington’s creative culinary spirit.

How to Spend a Day in Lexington: Places to and Things to Explore

Discover captivating destinations that encapsulate the essence of this vibrant city, creating memories that linger long after the sun sets. From bourbon tastings to historical landmarks and artistic marvels, here’s your guide to a day brimming with exploration in Lexington.

Bourbon Tasting

Lexington, a top-tier bourbon destination, invites you to savor its liquid gold. The Lexington Brewing & Distilling Co., nestled in the city’s heart, is the only brewery and distillery on the Kentucky Bourbon Trail. Town Branch® Bourbon flows here, with hourly tours and tastings offering a glimpse into seven generations of Irish brewers, distillers, and coopers.

For a memorable experience, opt for the Twilight and Cocktail Tour, where bourbon tales intertwine with the magic of the evening. And if you’re yearning for more bourbon adventures, Wild Turkey, Woodford Reserve, and Four Roses await just a short drive away, painting an intoxicating picture of Kentucky’s bourbon heritage.

Historical Tours and Retail Therapy

Beyond bourbon, Lexington unfolds its historical facets, inviting you to explore the childhood home of Mary Todd Lincoln. A self-guided tour from March to November unveils original artifacts, antique furniture, silver, and family portraits — a step back in time.

After a day of bourbon tastings and historical immersions, indulge in some retail therapy. Lexington’s boutiques, including Sash and Bow, Pirie Boutique, JamesC Boutique, Logan’s of Lexington, and Steel Mill & Co., promise unique finds and a glimpse into the city’s contemporary heartbeat.

Kentucky Wildcats Basketball

With 14 NCAA National Championships, the University of Kentucky boasts a basketball legacy that transcends the court. The enthusiasm is tangible at sports events in Lexington, with the city bathed in the iconic Kentucky blue.

Celebrities like Drake, Jennifer Lawrence, and Josh Hutcherson join the sea of blue, making a pilgrimage to the infamous Rupp Arena. It’s a spectacle, a celebration, and a testament to Lexington’s love for the game. And here’s a pro tip: never interrupt a UK fan during a game — a valuable lesson for a seamless Lexington experience.

Bourbon Distilleries

Venture beyond Lexington’s borders, and you’ll discover a plethora of bourbon distilleries within a short drive. You can explore Buffalo Trace Distillery, Castle & Key, and Woodford Reserve, each within 45 minutes of downtown, offering a journey into the heart of bourbon craftsmanship. Ask a local what to do in Lexington, and visiting a distillery will likely top the list.

Distillery District

The Distillery District, a bustling section of Lexington, encapsulates the city’s spirit. Home to James E. Pepper Distillery, Barrel House Distilling Co., Ethereal Brewing, Goodfellas Pizzeria, and Crank & Boom Ice Cream Lounge, this district is a fusion of tradition and modernity. It’s a can’t-miss experience where history, distilleries, and contemporary delights converge.

Keeneland Race Course

As the “Horse Capital of the World,” Lexington pays homage to its equestrian legacy at Keeneland Race Course—this National Historic Landmark, open year-round, hosts Thoroughbred races every April and October. Immerse yourself in horse racing with tours available all year, offering a behind-the-scenes peek into this iconic venue.

21c Museum Hotel and Lexington Mural Challenge

The 21c Museum Hotel adds an artistic twist to your Lexington exploration. With the first two floors as a rotating museum, you can sip cocktails at the Lockbox bar, surrounded by a vibrant art collection. As you venture downtown, the Lexington Mural Challenge unfolds — over 50 murals waiting for you to discover, a testament to the city’s commitment to the arts.

Historical Sites

Explore the historical tapestry of Lexington at Ashland, The Henry Clay Estate, and The Mary Todd Lincoln House. Henry Clay’s Public House, though not personally visited, comes highly recommended for its pub experience near the Old Courthouse.


In the tapestry of Lexington, bourbon flows, horses gallop, and history echoes. From spirited accommodations to culinary delights, from the roar of Rupp Arena to the tranquility of distilleries, Lexington is a symphony of experiences. As you explore this Kentucky gem, let the warmth of its people guide you, and may the memories you create be as rich and enduring as the traditions that define this city. In Lexington, every street, every bite, and every cheer is an invitation to savor life’s most flavorful moments.

Sabah Drabu

Co-Founder & CEO

Sabah Drabu is a foodie, engineer, and the Co-founder & CEO of CookinGenie. She created the platform in 2019 to connect local chefs with at-home diners, making hiring personal chefs more accessible. Sabah's idea has evolved into a service people use for parties, vacation rentals, and family gatherings.

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