
Guided tour · 2.5 hours
Lexington: Bluegrass Cocktails & Bites Walking Tour
Sink into your seat and sip unique craft cocktails and locally prepared plates while listening to captivating tales from Lexington's East End.
Charlie Brown's is a bar in Chevy Chase, Lexington.
Editorially verified August 18, 2026 by Elliot Marsh, TableJourney editor. Source.

Guided tour · 2.5 hours
Sink into your seat and sip unique craft cocktails and locally prepared plates while listening to captivating tales from Lexington's East End.

Guided tour · 3 hours
Embark on a journey through the heart of Downtown Lexington, where history and farm-to-table flavors intertwine for an afternoon of fun exploration.

Guided tour · 4 hours
Join us in the Distillery District for Kentucky farm-to-table cuisine, limestone-filtered bourbons, and an exploration into the history behind this revitalized piece o...
Address: 816 Euclid Ave, Lexington, KY 40502
The Obstinate Sons runs a snug bourbon bar and kitchen on Chevy Chase Place, a neighbourhood Lexington room that takes its whiskey list seriously.
DrinkBourbon pours with chef-driven plates
TipClosed Mondays; the kitchen holds its own, so arrive hungry rather than treating it as a drinks-only stop, and expect a wait for seats on weekends.
The Bar Complex runs three bars, a dance floor and drag stages on East Main, the long-standing anchor of LGBTQ+ nightlife in downtown Lexington.
DrinkDance-floor drinks before the drag show
TipThursday to Saturday only, 20:00 to 02:30; check the drag show schedule and arrive before the second set.
OBC Kitchen stocks over 150 bourbons and whiskeys behind a Lansdowne storefront, the Lexington bar-restaurant where bacon arrives in a glass with the drinks.
SignatureBacon in a glass
TipIt sits in the Lansdowne Shoppes beside sister steakhouse Malone's; weekend service opens at 10:00 with brunch dishes.
The Bluegrass Tavern stacks Kentucky's largest bourbon collection on Cheapside, the downtown Lexington bar where flights run deep into allocated bottles.
DrinkBourbon neat from Kentucky's largest bourbon collection
TipClosed Sundays and Mondays; tell the bartender a flavour direction and a budget and they will build a flight from Kentucky's largest bourbon collection.
Belle's Cocktail House pours bourbon cocktails across three levels on Market Street, with the rooftop bar downtown Lexington heads to on warm weekends.
DrinkBourbon cocktails on the rooftop
TipOpen Thursday to Saturday only, 16:30 to 02:00; head straight up to the rooftop level before the queue forms.
Ona mixes precise cocktails in an Art Deco room on Church Street, the low-lit downtown Lexington bar for a slow drink rather than a loud night.
DrinkHouse cocktails in an Art Deco room
TipOpen nightly from 17:00 to 01:00; the seasonal menu rotates, so ask the bartenders what they are testing this week.
The Obstinate Sons runs a snug bourbon bar and kitchen on Chevy Chase Place, a neighbourhood Lexington room that takes its whiskey list seriously.
DrinkBourbon pours with chef-driven plates
TipClosed Mondays; the kitchen holds its own, so arrive hungry rather than treating it as a drinks-only stop, and expect a wait for seats on weekends.