Today I’m sharing a guide to things to do in Lexington, Kentucky.

My friend Jenny and I spent two nights in Lexington and packed a lot into a short trip: seven restaurants, three distilleries, a bar, a racetrack, and a lively street festival. Lexington offers a rich mix of bourbon culture, horse-country history, great food, and public art. Below are highlights and recommendations to help plan your visit.

What to do in Lexington

Bourbon Trail

Several notable distilleries sit within a short drive of Lexington. Buffalo Trace, Castle & Key, and Woodford Reserve are all in nearby Woodford County and are typically within a 45-minute drive. Visiting a distillery is a top pick from locals and a great way to experience Kentucky’s bourbon heritage.

The Distillery District

The Distillery District blends industrial history with modern food and drink. In addition to distilleries like James E. Pepper and Barrel House Distilling Co., the area hosts Ethereal Brewing, Middlefork Kitchen and Bar, Goodfellas, and Crank & Boom. It’s a lively neighborhood that’s perfect for an afternoon of tasting and exploring.

Keeneland

Lexington is known as the “Horse Capital of the World,” and Keeneland Race Track is a must-visit. A National Historic Landmark, the grounds are open year-round. Races run in April and October, with special behind-the-scenes tours available during race seasons. Even outside race days, guided tours provide insight into the track’s history and operations.

Admire the Art at the 21c Museum Hotel

The first two floors of the 21c Museum Hotel in downtown function as a contemporary art museum with rotating exhibitions. A popular local routine is to enjoy a cocktail at Lockbox and then stroll the galleries to see the current installations.

Calumet Farm

Calumet Farm, a nearly 100-year-old thoroughbred breeding and training operation, sits adjacent to Keeneland. The farm closes during the annual Yearling Sale, but guided tours that include both Calumet and Keeneland are available and worth considering.

Admire the Murals

Downtown Lexington is sprinkled with vibrant street art—more than two dozen murals across the city. Walking the blocks around downtown and the Distillery District reveals many striking works and makes for an easy, free activity.

Ashland, The Henry Clay Estate

Ashland was the home of Henry Clay, a prominent 19th-century statesman. The estate, set in the heart of Lexington, played a role in the area’s Civil War history. The mansion and grounds are open for tours and provide a window into the city’s past.

The Mary Todd Lincoln House

The girlhood home of First Lady Mary Todd Lincoln is located downtown and offers interpretive tours. Special events and tours are sometimes scheduled to mark milestones like anniversaries or bicentennials.

Where to Eat and Drink in Lexington

Middlefork Kitchen Bar

Located in the Distillery District, Middlefork Kitchen Bar offers creative dishes with global influences. Standouts on the menu include Cacio e Pepe spätzle and scallion-cheddar pancakes. It was one of our favorite dinners on the trip.

Corto Lima

Corto Lima serves Latin-inspired dishes and is a great spot for shared plates. After touring distilleries we enjoyed queso, guacamole-stuffed arepas, tacos, and elotes—each bite was flavorful and satisfying.

Belle’s Cocktail House

Recommended by locals, Belle’s is known for inventive cocktails and a rooftop that offers downtown views. We didn’t make it there, but it comes highly suggested for a night out.

Crank & Boom Ice Cream Lounge

Crank & Boom, located near Middlefork and James E. Pepper, is the go-to scoop shop. They offer composed sundaes, ice cream flights, and bourbon-flavored options inspired by the region. The honey and bourbon flavor was a personal favorite.

Stella’s

Stella’s serves regional specialties like burgoo, a thick, hearty stew-like soup often made with beef and vegetables. We sampled it at the Jefferson Street Soiree and found it warming and flavorful—perfect for cooler weather.

Keeneland Track Kitchen

The track’s cafeteria serves excellent Southern breakfast fare—grits, eggs, bacon, potatoes, and biscuits. Arrive early to enjoy breakfast and then walk the grounds or watch the morning workouts for a true local experience.

Bluegrass Tavern

A laid-back spot frequently named one of the best bourbon bars in the South, Bluegrass Tavern is an excellent place to try rare pours and classic cocktails like an Old Fashioned.

Lockbox

Located inside the 21c Museum Hotel, Lockbox offers brunch with Southern flair. Highlights include baked eggs with cheesy grits and exceptional biscuits—perfect for a museum-breakfast combo.

The Village Idiot

This gastropub received multiple recommendations. We enjoyed spicy fried cauliflower and local beers there before heading out to explore the Jefferson Street Soiree.

Henry Clay’s Public House

Located in the Downtown Courthouse Entertainment District, this pub honors Henry Clay and his influence on Kentucky traditions, including the Mint Julep. It’s a recommended spot for classic pub fare and cocktails.

Annual Events in Lexington

Keeneland Races

Keeneland’s race meets in April and October are major draws. If your trip coincides with those months, plan in advance for tickets and special events.

Jefferson Street Soiree

The Jefferson Street Soiree is a one-night celebration where restaurants and live music take over the street. It’s a fun way to sample local food and enjoy community vibes.

Keeneland Yearling Sale

The Keeneland Yearling Sale is an annual auction where prospective owners bid on young thoroughbreds. Prices vary widely, from modest sums to multi-million-dollar purchases.

Have you been to Lexington? Share your favorite spots or tips in the comments—I’d love to hear your recommendations.

Read more about what to do in Lexington:

Lexington and the Bourbon Trail

This post was sponsored by Visit Lex. The opinions expressed are my own.