Drink in the view: Best Lexington rooftop bars, restaurants for a cocktail

One might get the impression that Lexington’s cocktail crowd suffers from fear of heights.

In a city which has a plethora of courtyards, patios and ground-level sidewalk tables for al fresco sipping, there is a dearth of outdoor spaces above the ground level reserved for the same pleasant past-time.

Only a handful of rooftop bars dot the city skyline, with one of them – Bangkok Lounge (formerly Roulay) - currently under redesign and not expected to re-open until later this summer.

Still, those who want fresh air to go along with their freshly made cocktails have a handful of options, each with its own style. So use this guide and list for the best rooftop bars that offer views of Lexington.

For the hipster

With its modern décor and minimalist vibe, Infinity Rooftop Restaurant & Bar has the feel of a hot spot in New York’s Tribeca or Atlanta’s Inman Park.

Located in the Residence Inn Lexington City Center, it boasts 25 tables and nine bar stools offering killer views of downtown (a few have a view of the Old Courthouse.)

In nice weather, the large windows and roof are left open, and patrons also are encouraged to enjoy their drinks around the Marriott’s rooftop pool. But before you think about wearing your bathing suit under your street attire, be aware that swimming is reserved for Marriott guests. So, enjoy a poolside drink, but not a plunge.

There are no Happy Hour prices, with all signature cocktails being $12, except for the Infinity Margarita which is $10.

According to Food & Beverage Director Jonah Gant, the bar’s top cocktails are Pink Martini (lemon vodka, grapefruit juice, lime juice and simple syrup) and the Moonlight Kiss.

“This is our spin on the French 75,” says Gant. “We use Castle & Key gin, house-made butterfly pea flower syrup, prosecco, soda water and lemon juice, resulting in a nice purple color. We then garnish it with an orchid.”

150 W. Main Street; 859-446-5605; infinityrestaurantandbar.com

Dog-friendly

If you’re not so much into “seeing and being seen” as kicking back and relaxing, opt for El Cid’s rooftop bar. Opened in June of 2021 in what was formerly Local’s on National Avenue, El Cid’s casual, laid-back roof terrace has eight tables which can accommodate up to 45 people.

Even better, six lucky patrons can bring along their furry friend as El Cid’s also has six doggy sofas and water bowls where your dog can enjoy water or whipped cream a la Starbuck’s popular Puppochino. If you choose the latter, you will be assured of having a drinking buddy for life.

As for your own refreshment, there is no Happy Hour, so they keep the drink prices reasonable. According to Front House Manager Demaria Powell, the Dulce Margarita, a sweet concoction of strawberry and pina colada, garnished with candy such as gummy worms and Airheads Extreme, is only $10.99.

701 National Avenue; 859-554-9977; elcidlexington.com

Most romantic

Those looking for a romantic date night spot need look no further than Dudley’s on Short. Lexington’s most elegant rooftop has a Charleston vibe with soft lighting, a lush garden designed by Jon Carloftis, and a breathtaking view of the spire at First Presbyterian Church on Market Street.

Ten tables and one couch provide seating for up to 35 people, although I have been here often and even when the rooftop is at full capacity, it never seems crowded.

“People always say they feel like they are somewhere other than Lexington when they come here,” says owner Debbie Long.

Don’t go expecting to find a separate bar on the roof as patrons make their drink choices from the main downstairs bar. Among the most popular choices according to Long are the St. Germain Cosmo (Tito’s vodka, St. Germain Elderflower Liqueur, lime juice, cranberry juice and pineapple juice) and the Pama-Rita (Camarena Silver Tequila, Pomegranate Liqueur, lime, cranberry and House Sour Mix.) Both cocktails are $14.

259 W. Short Street #125; 859-252-1010; dudleysonshort.com

Looking for a party

The rooftop at Belle’s Cocktail House always seems to have a lively group engaging in what might seem like a fraternity/sorority mixer for the (slightly) older crowd.

But don’t expect a kegger. This rooftop bar goes way beyond, with special cocktails such as Basic Bitch (pumpkin-spiced Tito’s Vodka, Songbird Liqueur, Bailey’s Irish Cream, simple syrup) or Naked in the Garden (cucumber-infused Wheatley Vodka, lemon juice, strawberry kiwi shrub, lemon slices, strawberry halves and cucumber slices.)

Both are concoctions that the bar’s patron saint, Lexington’s famous Madam Belle Brezing, would no doubt have approved of. Her bordello was known as “the most orderly of disorderly houses” – a slogan the current owners, brothers Justin and Seth Thompson, have embraced.

156 Market Street; events@bellesbar.com

With a chaser of UK Sports

Bear & the Butcher does not exactly fit the description of a rooftop bar, but it does have a second floor balcony with views of Chevy Chase, a bar and a TV which means that you don’t have to give up a UK football or basketball game to enjoy an evening out.

The balcony has six tables seating 20 people, with seating for an additional six at the bar. They have a daily Happy Hour from 4 p.m. to 6 p.m., but it doesn’t include their craft cocktails.

Go ahead and order them anyway, as for $9, you can get their two most popular drinks – Blue Steel (Wheatley Vodka, blueberries, lemon juice, simple syrup, Blue Curacao and sparkling wine) and Blue Blood Mojito (Kirk’n’Sweeney 12- year-old rum, sugar, fresh mint, soda, lime and muddled blueberries).

815 Euclid Avenue; 859-469-9188; bearandthebutcher.com

Best place to enjoy Thursday Night Live

Again, not having a rooftop bar, but a balcony, the Horse and Jockey is a Lexington version of a New Orleans French Quarter balcony bar.

The deck accommodates up to 75 people as they can re-arrange tables for any configuration, and there are bar stools along the railing overlooking Short Street.

Not content with just one bar, owner Paul Murphy, a transplanted Scotsman, has put in two – one open-air and one under a pergola (the latter being specifically devoted to gin and bourbon.)

Another specialty of his bar, according to Murphy, is that they grow all the herbs used in their cocktails.

“We grow lavender, mint, rosemary, and both English and German thyme,” he says.

If you haven’t been here yet, try the Lavender Chai Lemonade (Holi gin, fresh lavender and lemonade, $8) or the Black Walnut Old-Fashioned (Woodford Reserve Bourbon, simple syrup, cherry, orange peel and Black Walnut Bitters, $12).

131 Cheapside; 859-554-5585; horseandjockeypub.com

This story was originally published June 21, 2022 at 6:00 AM.