$$$$Cocktail barDowntownTue-Fri 17:00-02:00; Sat 17:00-02:30; closed Sun-Mon
The Bluegrass Tavern stacks Kentucky's largest bourbon collection on Cheapside, the downtown Lexington bar where flights run deep into allocated bottles.
TipClosed Sundays and Mondays; tell the bartender a flavour direction and a budget and they will build a flight from Kentucky's largest bourbon collection.
$$$$Cocktail barDowntownMon-Sun 17:00-01:00
Ona mixes precise cocktails in an Art Deco room on Church Street, the low-lit downtown Lexington bar for a slow drink rather than a loud night.
TipOpen nightly from 17:00 to 01:00; the seasonal menu rotates, so ask the bartenders what they are testing this week.
$$$$Cocktail barDistillery DistrictSun-Wed 17:00-24:00; Thu-Sat 17:00-02:30
Wiseguy Lounge hides a Prohibition-styled bourbon bar above Goodfellas Pizzeria on Manchester Street, Lexington's speakeasy with hundreds of bottles.
TipEnter through the pizzeria and head upstairs; Thursday to Saturday it pours until 02:30 with slices below.
$$$$Cocktail barDowntownThu-Sat 16:30-02:00
Belle's Cocktail House pours bourbon cocktails across three levels on Market Street, with the rooftop bar downtown Lexington heads to on warm weekends.
TipOpen Thursday to Saturday only, 16:30 to 02:00; head straight up to the rooftop level before the queue forms.
$$$$Cocktail barDowntownWed-Sat 16:00-02:30
Bourbon on Rye keeps Prohibition-era cocktails and 12 taps going until 02:30 on West Main Street, a late-shift bourbon room in downtown Lexington.
TipWednesday to Saturday only; kitchen plates pub classics late, which is rare downtown after midnight.
$$$$AmericanNorth LimestoneTue-Thu 17:00-00:30; Fri-Sat 17:00-01:30; Sun 17:00-00:30; closed Mon
Al's Bar anchors the corner of Sixth and Limestone with burgers, local beer and gigs, the long-running NoLi corner bar wired into Lexington's music scene.
TipClosed Mondays; Tuesday open mic is free and the Thursday to Saturday bookings range from hip-hop to bluegrass.
$$$$AmericanChevy ChaseMon-Thu 14:00-24:00; Fri-Sat 14:00-02:00; Sun 14:00-24:00
Chevy Chase Inn has poured since 1933, Lexington's oldest bar, a cash-friendly Euclid Avenue dive that opens at 14:00 and never pretends to be more.
TipAfternoon drinking is the move; it opens at 14:00 daily and the jukebox and regulars do the entertaining.
$$$$Cocktail barDowntownThu-Sat 20:00-02:30
The Bar Complex runs three bars, a dance floor and drag stages on East Main, the long-standing anchor of LGBTQ+ nightlife in downtown Lexington.
TipThursday to Saturday only, 20:00 to 02:30; check the drag show schedule and arrive before the second set.
$$$$Cocktail barNorth LimestoneMon-Sun 16:00-02:30
The Green Lantern books doom metal, bluegrass and punk into a West Third Street dive, one of Lexington's most-loved and longest-running dive rooms.
TipCash helps at the bar; Wednesday karaoke and the happy hour before 19:00 are the reliable nights.
$$$$AmericanChevy ChaseSun-Thu 11:00-23:00; Fri-Sat 11:00-01:00
Charlie Brown's furnishes its Euclid Avenue bar like a worn library, all couches, bookshelves and lamplight, a Lexington comfort institution with pub food.
TipGrab a couch by the fireplace in winter; the kitchen serves the full menu until late on weekends.
$$$$AmericanDowntownMon-Sun 11:00-02:30
McCarthy's Irish Bar pulls Guinness on South Upper Street daily until 02:30, the downtown Lexington local for march-in singalongs and post-game pints.
TipOpen 11:00 to 02:30 every day; it is the default St Patrick's headquarters, so plan around the March crush.