Condé Nast’s top choices for your perfect Lexington weekend – where to stay, where to shop, where to drink, where to eat and where to play.

Ashlea Halpern from Condé Nast has discovered the perfect places to pop into during your stay in Lexington, revealing her guide to the top attractions in and around town. Check out her full thoughts here.



21c Museum Hotel

167 West Main Street

Lexington’s newest boutique museum-hotel offers chic, modern guest rooms, rotating artwork exhibitions and a trendy restaurant, Lockbox, that serves Kentucky-inspired cuisine from acclaimed chef Jonathan Searle. Rooms book quickly, especially on busy weekends, so reserve your room early!

Lyndon House

507 North Broadway

A historic redbrick mansion turned bed & breakfast, the Lyndon House offers quaint guest rooms with period furnishings and made-to-order breakfasts in their refined dining room.


Beyond Grits: Downtown Restaurants


County Club

555 Jefferson Street

One of the pioneers in Lexington’s smoked meat scene explosion, County Club has an industrial ambiance and a kitchen that has mastered the art of meat smoking. Check out what’s cooking on their ever-changing blackboard-style menu, or ask about the smoked meat of the day.

Crank & Boom

1210 Manchester Street

A small batch craft ice cream shop in Lexington’s Distillery District that serves velvety ice cream in a variety of inventive flavors. Try the Bourbon & Honey, Superfudge or the Kentucky Blackberry & Buttermilk!

Smithtown Seafood and West Sixth Brewing

501 West Sixth Street

Grab a platter of wild-caught fried catfish or some fish tacos at this fast-casual dining locale serving fresh fish sourced from neighboring indoor commercial Aquaponics farm Food Chain. You can also chow down in the adjacent West Sixth Brewing’s tap room and wash it down with a classic West Sixth IPA.

Blue Door Smokehouse

226 Walton Avenue

Best brisket in town. Enough said.

Missy’s Pies, Etc.

502 East High Street

A Lexington staple since 1989, Missy’s is most famous for their indulgent pies – but they do offer a selection of soups, sandwiches, coffee and other bakery items if you’re hungry for a good meal. Pie must-try’s include the Peanut Butter Pie, the Black Bottom Banana Pie and the Chocolate Brownie Pie.



The Kentucky Bourbon Trail Craft Tour

Bluegrass Region

Taste the refined flavors and learn the secrets of some of Kentucky’s smaller craft distilleries. You can taste handcrafted brands, learn the tricks of the bourbon trade and collect stamps for your Craft Tour Passport at each stop.

Bluegrass Distillers

501 West Sixth Street

A craft bourbon distillery in the heart of downtown Lexington, Bluegrass Distillers formulate its recipes in-house and hand-crafts each of its batches using local ingredients. Stop in to view their beautiful 250-gallon copper still where the magic happens.

Barrel House Distilling Co.

1200 Manchester Street

Located in Lexington’s hip Distillery District, Barrel House is a craft distillery distilling bourbon, vodka, rum and moonshine, which includes their long-awaited RockCastle Bourbon, the first bourbon distilled on the historic James Pepper Distillery’s campus in more than 65 years.



Keeneland Race Course

4201 Versailles Road

One of the world’s most beautiful and iconic Thoroughbred race courses, Keeneland is one of Lexington’s most popular attractions, with race meets occurring during the months of April and October.

Old Friends Thoroughbred Retirement Farms

1841 Paynes Depot Road, Georgetown

Many of Kentucky’s legendary racehorses retire to this home for Thoroughbreds after celebrated careers. Visitors can take tours of their facilities and learn about the lives and careers of the former champions.

Kentucky Horse Park

4089 Iron Works Parkway

A sprawling 1,200-acre park in the heart of Horse Country, the Kentucky Horse Park is a world-renowned attraction and also houses the Smithsonian-affiliated International Museum of the Horse.