Take a stroll down lively Jefferson Street and discover the best places to eat, drink and take in the bustling scene.


The historic Western Lexington area has seen a revival over the past several years, with an influx of fantastic restaurants concentrated around the Jefferson Street corridor. You’ll find everything from Southern delis to white-tablecloth steakhouses on this stretch. If you find yourself here in September, see if you can catch the Jefferson Street Soiree, a block party celebrating Keeneland’s annual Yearling Sale featuring dozens of local food vendors, live music and bourbon-infused libations.


West Sixth Brewery/Smithtown Seafood

501 West Sixth Street                                                                                                                                         Located on the far north side of Jefferson as it dead ends into Sixth street is popular brewery West Sixth and adjoining restaurant Smithtown. Grab a platter of fried fish at Smithtown, sourced from neighboring indoor commercial Aquaponics farm Food Chain, and grab a seat in West Sixth’s taproom. Menu picks: Wild-caught fried Catfish, Fish Tacos (Smithtown), West Sixth IPA, Pay-it-Forward Cocoa Porter (West Sixth) westsixth.com

County Club

555 Jefferson Street

Emphasizing the tradition of smoking meats using hardwoods and low temperatures, County Club’s mouthwatering meats are sourced from local farms and served in a stylish industrial space. Their blackboard specials are always a hit, but you can’t go wrong with their menu staples either. Menu picks: Poutine, Salad or Meat Special, Smoked Garlic Potato Hash (Brunch only, Sundays 11-3) countyclubrestaurant.com

Chase Tap Room

286 Jefferson Street

On the corner of Third Street and Jefferson sits a micro-brewery, coffee hub and pizza place all housed in one urban, open-air setting. Brewing new and inventive beers right in their back room, their taps rotate on a weekly basis – and if you’re in the mood for a game of darts, you’ve come to the right place. chasebrewing.com


218 Jefferson Street

A hidden “hive” nestled behind rustic brick walls; the Apiary is one of Lexington’s most sophisticated entertaining spaces. You can do a walk-by and peek in at their gardens or schedule a tour if you’re interested in the event space. the-apiary.com


191 Jefferson Street

An elegant wine and Spanish-style tapas bar with a wine list curated by Lexington’s only certified Sommelier, Enoteca offers a stylish and rustic ambiance in its cozy interior and quaint outdoor patio. Menu picks: Chorizo puffs, Stuffed Mushrooms, Gamba al ajilo. enotecalex.com



486 West Second Street                                                                                                                                       Escape into this boutique deli, market, wine, craft beer and specialty liquor shop located on the corner of Second Street and Jefferson to browse fine wines, cheeses, macaroons and more along with a selection of fresh sandwiches and salads. They also offer free weekly wine tastings on Friday evenings from 5-8pm. Menu Picks: Morbier and Argula Sandwich, Three-Bean Salad. wineandmarket.com

Blue Heron Steakhouse

185 Jefferson Street

A cozy-chic steakhouse and cocktail bar, Blue Heron’s menu features a mix of steakhouse classics and Southern fare with an impressive wine and cocktail list to boot. The charming ambiance features a two-sided wood burning fireplace, or in warmer weather you can relax on their outdoor patio facing Jefferson Street. Menu picks: Porterhouse Steak, Grilled thick cut bacon appetizer, The Blue Heron cocktail. blueheronsteakhouse.com

Nick Ryan’s

157 Jefferson Street

A neighborhood restaurant and bar featuring a winding Southern double porch, Nick Ryan’s offers contemporary American cuisine and Prohibition-era drinks in a relaxed and comfortable atmosphere. Menu picks: Shrimp & Grits, Hot Brown, Braised Beef Short Ribs. nickryans.com

Grey Goose

170 Jefferson Street                                                                                                                                                 Thin crust New York-style pizzas are the name of the game here, along with a variety of pub appetizers and entrees. Dine in their semi-outdoor area modeled after a horse stable, or sneak back to their patio for an urban oasis experience. Menu picks: Italian Pizza, Hot Brown Pizza, Black Bean Burger greygooserestaurants.com


Stella’s Kentucky Deli

143 Jefferson Street

Inside a sunny yellow house on the south side of Jefferson is this beloved locavore deli offering creative sandwiches, soups and salads with classic Southern twists. Open for brunch, lunch and dinner, Stella’s offers an easygoing, homey atmosphere and locally loved cuisine. Menu Picks: Fried Green Tomato BLT, Grilled PB&J, Pimento Cheese. stellaskentuckydeli.com

Wagon Bones Grill

591 West Short Street

This authentic, “family-owned and homegrown” BBQ joint serves up plates of savory meats seasoned with blends of Memphis-style and Western Kentucky spin dry rub, smoked for 15 hours and finished off with a secret family sauce. Menu picks: Brisket, Pulled Pork, Cherry Cobbler. Wagon Bones Grill