The Best of Lexington, KY: Iconic Stops + Hidden Gems
Whether you’re looking for iconic experiences or want to explore hidden gems, here are some fun things to do in Lexington, Kentucky. Image: VisitLEX
Lexington may be best known as the Horse Capital of the World, but there’s much more to explore beyond its famous Thoroughbred culture. From longtime local institutions to tucked-away restaurants, outdoor adventures, and experiences you might not expect, there’s always something new to discover. We’ve rounded up some can’t-miss classics, along with a few unexpected gems worth adding to your itinerary. Here are some fun things to do in Lexington, Kentucky!
Table of Contents
Lexington Classics
Chevy Chase Inn
Area: Chevy Chase
More Info: instagram.com
Opened in 1933 as the Blue Goose, Chevy Chase Inn is Lexington’s oldest continuously operating bar, serving beer in what was once a new development on the city’s outskirts. Today, you can kick back with a cocktail and enjoy live music, a dog-friendly patio, and chatting up a lively mix of longtime regulars and newcomers.
Coles 735 Main
Area: Downtown
More Info: coles735main.com
Set in a restored 1938 landmark, Coles 735 Main pairs Southern hospitality with seasonal goodness. Here, you can enjoy locally sourced ingredients, house-cured meats, and fresh-baked breads, alongside an impressive selection of handcrafted cocktails, hundreds of bourbons, and an award-winning wine program. Dinner reservations are recommended.
Henry Clay Estate
Area: Ashland Park
More Info: henryclay.org
Known as Ashland, this 17-acre estate was home to Henry Clay, a U.S. senator, House speaker, secretary of state, and presidential candidate known as the “Great Compromiser.” Guided tours take place from March through December, giving you a chance to explore his political legacy and family history.
Keeneland
Area: West Lexington
More Info: keeneland.com
Surrounded by the city’s rolling Bluegrass landscape, this National Historic Landmark has been a prime location for Thoroughbred racing and sales since 1936. The track comes alive during the spring and fall race meets, but you don’t need a race ticket to experience the space, as Keeneland welcomes visitors year-round.
Book a tour, watch morning workouts, browse the Keeneland Library, or grab breakfast at the Track Kitchen for a true Kentucky experience.
Kentucky Horse Park
Area: North Lexington
More Info: kyhorsepark.com
Part working horse farm, museum, and international competition venue, this 1,229-acre park showcases more than 40 breeds during its main season. You can meet racing legends, watch breed and draft-horse presentations, tour the International Museum of the Horse, or try horseback riding — all on site. And don’t miss the grave of Man o’ War, an American Thoroughbred known as one of the greatest racehorses of all time.
Main-season admission includes a free return visit the following day (except during major events and holidays) in case you miss anything!
The Kentucky Theatre
Area: Downtown
More Info: kentuckytheatre.org
One of the country’s few surviving movie palaces, The Kentucky Theatre has been around since 1922. Now a nonprofit-managed arthouse, it hosts first-run independent films, concerts, festivals, and beloved local traditions like midnight showings of The Rocky Horror Picture Show.
Mary Todd Lincoln House
Area: Downtown
More Info: mtlhouse.org
Originally built between 1803 and 1806 as an inn, this Federal-style house was the girlhood home of Mary Todd Lincoln, the Lexington-born first lady and wife of President Abraham Lincoln. Take a guided (or self-guided) tour to explore the period furnishings, family portraits, and original artifacts in this space that has served as a boarding house, grocery store, brothel, and storage space before becoming a museum.
Windy Corner
Area: North Lexington
More Info: windycornermarket.com
This cheerful country cafe is owned by Ouita Michel, one of Kentucky’s best-known chefs and restaurateurs. Serving Kentucky comfort food made with locally sourced ingredients, you’ll find everything from po’boys, burgers, and seafood baskets to salads, bakery treats, and weekend brunch. Shop shelves stocked with Kentucky-made pantry goods perfect for gifting (or keeping!).
Unexpected Lexington Finds
Black Soil KY
Area: Garden Springs
More Info: blacksoilky.com
Dedicated to expanding market opportunities for Black farmers, growers, and producers, this organization connects consumers with local food through its fulfillment center, markets, partnerships, and educational programs.
Highlights include farm-to-table dinners and the Homesteader Farm Tour Series. To make your planning easy, tickets for these countryside excursions often bundle admission, lunch, and transportation from Lexington.
Bites of the Bluegrass
Area: Varies
More Info: bitesofthebluegrass.com
Blending food and history, Bites of the Bluegrass offers a three-hour flagship walking tour that takes you through downtown. You’ll stop at four to five local eateries to enjoy small plates while learning a little more about the city’s history. Other tours include the Distillery District, Warehouse Block, True Crime, and LGBTQ history. The entire walk is just under a mile, and groups max out at 12 people.
Boone Creek Outdoors
Area: Boone Creek
More Info: boonecreekoutdoors.com
Calling all adventure seekers! Boone Creek Outdoors’ two-and-a-half-hour canopy tour will get your adrenaline going with six ziplines, three sky bridges, a rappel, and floating stairs (the longest flight stretches almost 1,400 feet!).
Want more? There’s a 16-obstacle challenge course, an introductory zipline option, and guided hikes to add to the fun. Be sure to make reservations, wear closed-toe shoes, and review the rules, which include height and weight requirements.
DV8 Kitchen
Areas: South Broadway and East End
More Info: dv8kitchen.com
This fast-casual bakery and café provides second-chance employment and life-skills training for people in substance-use recovery. Both locations offer all-day breakfast and lunch options, including favorites like the brioche sandwich and signature cinnamon roll. You can also pick up a loaf of sourdough to take home. Be sure to check out the tabletops, which feature artwork tied to recovery organizations.
Kentucky Native Café
Area: Aylesford
More Info: michlers.com
Hidden behind Michler’s Florist, Kentucky Native Café feels like a secret garden. Follow a greenhouse path to dining tables tucked beneath trees and string lights, and choose bites from a rotating menu that typically includes soups, sandwiches, small plates, and more. Check the chalkboards near the checkout stand for the daily menu, and get there early — seating is on a first-come, first-served basis.
Loudoun House
Area: Castlewood
More Info: lexingtonartleague.org
Designed by architect Alexander Jackson Davis and completed around 1851, this Gothic Revival villa is one of only five surviving Davis designs of its kind in the U.S. Today, the Lexington Art League fills the home’s historic rooms with rotating exhibitions, artist studios, classes, and events. Admission is free and includes access to the surrounding grounds of Castlewood Park for additional exploration.
Mileta Restaurant
Area: Fayette Mall
More info: miletarestaurant.com
Mileta may be located in a mall, but it’s not food court fare. This moody, midcentury-inspired dining room features globally inspired dishes prepared in a scratch-kitchen. Highlights include handmade pasta paired with seasonal small plates, raw-bar selections, sourced entrées, and more. The bar and lounge welcome walk-ins, but dining room reservations are encouraged. Save room for the Parmesan soft serve for dessert!
Raven Run Nature Sanctuary
Area: Southeast Lexington
More Info: ravenrun.org
If you’re a nature lover, you will appreciate Raven Run’s 734 acres of meadows, woodlands, streams, and Kentucky River palisades. Ten miles of routes, ranging from paved paths to rugged woodland trails, lead to a 70-foot river overlook and an early settlement homestead. Admission is free, but it’s best to arrive early on weekends, as entry pauses once the parking lot reaches capacity.
Silver Springs Farm
Area: Leestown Road
More Info: silverspringsfarm.net
Just five miles from downtown, Silver Springs Farm is located on the site of the former Silver Springs Distillery, which was once associated with whiskey pioneer James E. Pepper. Today, owners Allen and Leslie Carter live and work on the land, breeding racehorses and producing wine from an on-site vineyard. Private tastings are available by appointment only for groups of six to 12.
Trifecta Design Studio
Area: Warehouse Block
More Info: trifectadesignstudio.com
If you’ve ever wanted to try your hand at glass blowing, visit Trifecta, where you can take classes or shop the gallery. While glass art is the star of the show, Trifecta is also home to a hidden gem: an intimate cocktail lounge concealed behind a mirrored gallery door. Handcrafted cocktails and curated spirits are available on a first-come, first-served basis in this moody, vintage-inspired hideaway.
Happy exploring!
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Lennie Omalza
Originally from Hawaii, Lennie Omalza is a Louisville-based freelance writer of over 18 years. Lennie is a yoga-loving foodie who travels as often as she can and enjoys writing about food, homes, and weddings. You can find more of Lennie's work at Eater, Hawaii Home & Remodeling, and The Louisville Courier-Journal.