$$$$Cocktail barDowntown
The Bluegrass Tavern stacks Kentucky's largest bourbon collection on Cheapside, the downtown Lexington bar where flights run deep into allocated bottles.
TipClosed Sundays and Mondays; tell the bartender a flavour direction and a budget and they will build a flight from Kentucky's largest bourbon collection.
$$$$Cocktail barDowntown
Belle's Cocktail House pours bourbon cocktails across three levels on Market Street, with the rooftop bar downtown Lexington heads to on warm weekends.
TipOpen Thursday to Saturday only, 16:30 to 02:00; head straight up to the rooftop level before the queue forms.
$$$$Cocktail barDowntown
Ona mixes precise cocktails in an Art Deco room on Church Street, the low-lit downtown Lexington bar for a slow drink rather than a loud night.
TipOpen nightly from 17:00 to 01:00; the seasonal menu rotates, so ask the bartenders what they are testing this week.
$$$$Cocktail barDowntown
Bourbon on Rye keeps Prohibition-era cocktails and 12 taps going until 02:30 on West Main Street, a late-shift bourbon room in downtown Lexington.
TipWednesday to Saturday only; kitchen plates pub classics late, which is rare downtown after midnight.
$$$$Cocktail barDistillery District
Dark Arts Whiskey House finishes barrels in Lexington's Distillery District and pours cask tastings on Manchester Street, a Kentucky Bourbon Trail stop.
TipBook the barrel tasting; pulling your pour straight from an ageing cask beats the standard flight.
$$$$Cocktail barDistillery District
Wiseguy Lounge hides a Prohibition-styled bourbon bar above Goodfellas Pizzeria on Manchester Street, Lexington's speakeasy with hundreds of bottles.
TipEnter through the pizzeria and head upstairs; Thursday to Saturday it pours until 02:30 with slices below.
$$$$Cocktail barNorth Limestone
The Green Lantern books doom metal, bluegrass and punk into a West Third Street dive, one of Lexington's most-loved and longest-running dive rooms.
TipCash helps at the bar; Wednesday karaoke and the happy hour before 19:00 are the reliable nights.
$$$$Cocktail barDowntown
The Bar Complex runs three bars, a dance floor and drag stages on East Main, the long-standing anchor of LGBTQ+ nightlife in downtown Lexington.
TipThursday to Saturday only, 20:00 to 02:30; check the drag show schedule and arrive before the second set.
$$$$Cocktail barDistillery District
Wiseguy Lounge hides a Prohibition-styled bourbon bar above Goodfellas Pizzeria on Manchester Street, Lexington's speakeasy with hundreds of bottles.
TipEnter through the pizzeria and head upstairs; Thursday to Saturday it pours until 02:30 with slices below.
$$$$Cocktail barDowntown
Bourbon on Rye keeps Prohibition-era cocktails and 12 taps going until 02:30 on West Main Street, a late-shift bourbon room in downtown Lexington.
TipWednesday to Saturday only; kitchen plates pub classics late, which is rare downtown after midnight.
$$$$Cocktail barNorth Limestone
The Green Lantern books doom metal, bluegrass and punk into a West Third Street dive, one of Lexington's most-loved and longest-running dive rooms.
TipCash helps at the bar; Wednesday karaoke and the happy hour before 19:00 are the reliable nights.
$$$$Cocktail barDowntown
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.
TipThursday to Saturday only, 20:00 to 02:30; check the drag show schedule and arrive before the second set.