Ultimate 3-Day Lexington Itinerary: Best Things to Do & See

Start your Lexington adventure with a visit to the legendary Keeneland Race Course. Explore the historic grounds, watch morning thoroughbred workouts, and soak up the atmosphere of one of America’s most beautiful racetracks.

Keeneland Race Course

Enjoy a farm-to-table breakfast at Josie's, a cozy local favorite known for hearty Southern classics and great coffee.

Josie's

Immerse yourself in Kentucky’s storied past at the Mary Todd Lincoln House, the fascinating childhood home of Abraham Lincoln’s wife, offering guided tours and rich local history.

Mary Todd Lincoln House

Stroll the picturesque Gratz Park neighborhood, a charming district lined with 19th-century homes and shaded by ancient trees.

Gratz Park

Dine at Distilled on Jefferson, a modern Southern restaurant set in a historic mansion, known for creative cocktails and seasonal ingredients.

Distilled on Jefferson

Wrap up your first night with a craft cocktail or flight of Kentucky bourbon at the inviting Lockbox bar inside the 21c Museum Hotel, where art installations meet creative mixology.

Lockbox

Begin with a guided tour at the celebrated Ashland The Henry Clay Estate, strolling the beautiful gardens and learning about the life of the “Great Compromiser.”

Ashland The Henry Clay Estate

Treat yourself to a hearty Southern breakfast at Doodles, a beloved brunch spot in a restored service station, famous for local grits and their “Kentucky Hot Brown.”

Doodles

Take a scenic drive to Woodford Reserve Distillery, nestled in the rolling hills outside Lexington, for a guided bourbon tasting and behind-the-scenes look at Kentucky’s finest whiskey.

Woodford Reserve Distillery

Enjoy a late lunch in the heart of horse country at Wallace Station, a charming deli with famous sandwiches, fresh-baked desserts, and scenic patio seating.

Wallace Station

Head back to town and sample small-batch spirits at Barrel House Distilling Co, a craft distillery in the historic Lexington Distillery District, perfect for bourbon and cocktail lovers.

Barrel House Distilling Co

Dinner at Goodfellas Pizzeria in the Distillery District—grab a New York-style slice and enjoy the lively, industrial-chic vibe with plenty of local brews on tap.

Goodfellas Pizzeria

Begin with a walk and birdwatching at the serene Raven Run Nature Sanctuary, a 734-acre preserve with miles of trails through wildflower meadows and forest along the Kentucky River.

Raven Run Nature Sanctuary

Head to North Lime Coffee & Donuts for inventive, freshly made donuts and locally roasted coffee—a Lexington breakfast staple.

North Lime Coffee & Donuts

Explore the galleries at 21c Museum Hotel, a boutique hotel and contemporary art museum in one, featuring rotating exhibitions and interactive installations.

21c Museum Hotel

Lunch at the trendy DV8 Kitchen, a bakery and café with a mission, serving up gourmet sandwiches, scratch-made pastries, and hope to those in recovery.

DV8 Kitchen

Dive into neighborhood vibes and creative cuisine at The Local Taco, a laid-back spot offering Southern-inspired tacos, house-made salsas, and a great selection of bourbon cocktails.

The Local Taco

Finish your trip at West Sixth Brewing, a lively local brewery with creative craft beers, a welcoming beer garden, and frequent community events.

West Sixth Brewing