
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.
Belle's Cocktail House is a rooftop bar in Downtown, Lexington.
Editorially verified August 18, 2026 by Elliot Marsh, TableJourney editor. Source.
Tip: Head straight for the roof before 21:00 on Saturdays; the lower floors absorb the overflow once it fills.

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: 156 Market St, Lexington, KY 40507
The Bar Complex has long anchored LGBTQ+ Lexington, stacking drag shows, a dance floor and three bars into one East Main address.
TipDrag showtimes post on the venue's socials weekly; Thursday is the calmer night to actually talk.
Crossings pours nightly on North Limestone as Lexington's offbeat gay cocktail bar, with drag nights, leather nights and a loyal neighbourhood crowd.
TipOpen 16:00-02:30 every day of the week, which makes it the reliable early-evening LGBTQ+ meeting point downtown.
McCarthy's Irish Bar stays open to 02:30 every single night on South Upper, the downtown Lexington constant for a last Guinness after everything else.
TipIt opens at 11:00 and never really empties on game days; late weeknights are when the regulars hold court.
Wiseguy Lounge pours hundreds of bourbons in a Prohibition-styled room above Goodfellas Pizzeria, Lexington's speakeasy hiding over the pizza ovens.
TipEnter through the pizzeria and take the stairs; a slice downstairs at 01:00 is the correct way to end it.
The Bar Complex has long anchored LGBTQ+ Lexington, stacking drag shows, a dance floor and three bars into one East Main address.
TipDrag showtimes post on the venue's socials weekly; Thursday is the calmer night to actually talk.
Crossings pours nightly on North Limestone as Lexington's offbeat gay cocktail bar, with drag nights, leather nights and a loyal neighbourhood crowd.
TipOpen 16:00-02:30 every day of the week, which makes it the reliable early-evening LGBTQ+ meeting point downtown.
Chevy Chase Inn, pouring since 1933, is Lexington's oldest bar and its definitive dive, all cheap bottles, a jukebox and Euclid Avenue regulars.
TipIt opens at 14:00 daily; afternoon barstool conversation is the real programme here, not the nightcap rush.
The Green Lantern holds West Third Street down as Lexington's late dive of record, open to 02:30 nightly with bands, karaoke and cheap cans.
TipKaraoke Wednesdays and the pre-19:00 happy hour are the moves; bring cash to keep the line moving.
McCarthy's Irish Bar stays open to 02:30 every single night on South Upper, the downtown Lexington constant for a last Guinness after everything else.
TipIt opens at 11:00 and never really empties on game days; late weeknights are when the regulars hold court.