By Madison Rexroat



Located on the penthouse floor of a high rise at Cheapside Park, Skybar’s panoramic view of downtown Lexington isn’t the only attraction. With a full service bar and bottle service, as well as a beloved sushi bar, Skybar is the “go-to” spot to unwind after Thursday Night Live or to simply hang out with friends. The dance floor conveniently flows into the bar and lounge area, and live music ranging from upbeat DJs to live piano classics are featured. You can reserve private rooms, fully equipped with bars and couches, or you can enjoy the atmosphere as you sip your favorite cocktail, plum wine or Japanese sake.

269 W Main St. Penthouse • (859) 368-7900


Belle’s Cocktail House is committed to serving spectacular drinks with distinct character. The bar is named after Lexington’s most famous madam, Belle Brezing, and you can even ask to see the book behind the bar to learn more about her life and legacy. But the focus at Belle’s is on the drinks. With a lounge area upstairs, including a bar with over 50 bourbons and décor that radiates a rugged cabin feel, guests can enjoy signature drinks like the Gatewood’s Manhattan (which turns a traditional Manhattan into an artfully smokey drink with the addition of Sombra Mezcal) in a relaxed environment that pays tribute to the culture that inspired it. 

156 Market St. • (859) 389-6777


With a name that literally translates from Italian to “wine library,” Enoteca is just that. Featuring a large selection of wines, bourbon and craft brews, guests can sample various concoctions while enjoying Spanish-inspired tapas” recommended by Enoteca’s educated staff members to create delectable beverage and food pairings. Enoteca also provides a chic atmosphere perfect for a date night or an outing with the girls. Their softly lit patio and upstairs deck is a favorite among Lexingtonians, and the vibrant seasonal menu makes for a distinct experience each time you visit. Enoteca’s classic cocktails range from the Cava Cocktail (Copper & Kings Brandy, bitters, Spanish sparkling wine, sugar cube) to the Townie (Town Branch bourbon, ginger beer, pistachio liqueur, lemon juice, cherry garnish). Paired with their chocolate bourbon almond stuffed figs for dessert, you’ve got the makings of a perfect cocktail experience.

191 Jefferson St. • (859) 687-0346 •


Having been on multiple “best bars” lists, it’s easy to see why Bluegrass Tavern has been called the “Mecca of bourbon.” With a collection of 450 plus bottles – a lot of them being bourbon – Bluegrass Tavern is a haven for bourbon and cocktail lovers, alike. The Old Fashioned is a Bluegrass Tavern favorite, with the Manhattan coming in at a close second. While seated at the bar or at big barrel tables, guests can enjoy live music while sampling rare bourbons and delicious cocktails prepared by the skilled BT bartenders. 

115 Cheapside • (859) 389-6664 •


At Parlay Social, you can revisit the Prohibition Era, complete with art deco décor and live music by local bands, all within the comfort of 21st century Lexington. Creating a balance between theatrics and style, Parlay Social offers an upscale but relaxed ambiance. Guests can enjoy champagne, wine, premium liquors and craft, domestic and imported beer. And we can’t forget about the cocktails! Signature cocktails like the Keeneland Breeze, Blue Margarita and My Old Kentucky Home make Parlay Social a hotspot on everyone’s cocktail bucket list. 

249 W Short St. • (859) 244-1932 •