Nightingale is Calling
BY DATHAN KAZSUK | PHOTOS BY JESSICA BRATTON
FOOD STYLING & PHOTO ASSISTANCE BY RACHEL DANIELLE
It was a cool night in downtown Holly Springs—the kind of evening where the air hums with possibility and the clinking of cocktail glasses sets the soundtrack—and it was only Thursday.
Along with my wife (and fellow 5 West writer) Jennifer Primrose, I strolled into Nightingale, the rooftop bar quickly becoming the town’s worst-kept secret. Perched above Main Street, it’s a blend of elegance and edge—think bold wallpaper, moody lighting and a vibe that says, “Yeah, we’re fancy, but we know how to have fun.”
From the “brunch room” beaming in every shade of yellow to the “bird room,” where the walls flaunt a flock of clever nods—Bye Bye Birdie, Divine’s Pink Flamingos, The Mighty Ducks, and yes, even Larry Bird—Nightingale pulls you in with its bold, quirky charm. Every corner feels like a stylish wink, small in scale but sharp in detail.
Chris Harol, co-owner of Nightingale, greeted us with the kind of easy charm you’d expect from someone who has built not only a bar, but an experience. “We wanted to create something that felt like a big city night out without having to drive 30 minutes into Raleigh,” Harol explains as we settle into a prime spot on the rooftop, the rays of the Holly Springs evening twinkling below.
The concept for Nightingale didn’t hatch overnight. Harol, his brother and their business partners spent years watching the top of the building sit empty, deal after deal—restaurants falling through, failing to sign on that dotted line.
Finally, they decided to take matters into their own hands. “I always had it in the back of my mind—it’d be fun to do my own thing,” he says. “When the last deal fell through, I thought, ‘Alright, it’s time.’”
What they’ve created is more than a bar; it’s a culinary playground. The menu started with small plates, perfect for sharing and sampling, but as Harol quickly learned, Holly Springs wasn’t quite ready for just avant-garde bites and fancy cocktails. “It was popular for girls’ night—small plates, cocktails—but we kept hearing people ask for something heartier,” he admits with a laugh. “So now we’re moving toward adding more large plates, too; something for everyone.”
And the food? Oh, it’s not just an afterthought—it’s a full-on rustic feast courtesy of Christy Griffith, executive chef and Harol’s business partner. She and her husband Matt (another partner in the business) happen to own the beloved Pimiento Tea Room, conveniently perched just across Main Street.
“It makes sense that our dishes pair well with our signature cocktails, because our beverage program focuses just as much on highlighting seasonal ingredients as our kitchen does,” says Griffith. “We don’t necessarily work in tandem on menu development, but both our food and beverage menus always seem to complement each other because of our attention to seasonality.”
Griffith’s whipping up dishes that hit the perfect balance of cozy and creative—like the Whipped Feta, which is dressed to impress with toasted almonds, hot apple honey and house-made olive oil crackers, or the Gnocchi Bravas, fried sweet potato gnocchi lounging in aioli and bravas sauce—both of which we happily devoured while swapping stories with Harol.
But that’s just the start. The menu at Nightingale keeps things interesting with bites like the ostrich and feta burger with sundried tomato mayo and rosemary lemon fries. “Small plates, larger plates—it’s all there, and before we knew it, our table was a rustic masterpiece of flavors and flair,” says Griffith on Nightingale’s latest seasonal menu, available now.
But let’s talk cocktails, because Nightingale isn’t just about the food. It’s about the art of the drink, and that’s where Zach Thomas stepped in. If you don’t know Thomas, you’re missing out. He’s the kind of guy who casually drops cocktail history facts from the 1700s while mixing a drink so smooth it feels like liquid gold.
Thomas has left his mark on some of the hottest spots around—Killjoy, Crawford and Son, Fox Liquor Bar, Foundation and The Crunkleton, just to name a few. Calling him anything less than a mixology master? Well, that’s just lying to yourself. At Nightingale’s Cocktail Club—a monthly rendezvous of craft and charisma—guests sip their way through a curated drink lineup while learning the history and technique of crafting drinks. It’s part education, part entertainment, and all delicious.
The Cocktail Club isn’t just about drinking—it’s an experience. For a lifetime membership ($195), you get access to three specialty cocktails at each event, discounts on future drinks, swag like signature glasses and T-shirts, and even your name on a plaque at the bar. The crowd has grown fast, with nearly 45 members and counting, and the goal is to hit 100 by the end of the year.
And if you’re into rare spirits, Nightingale has you covered with its Break Even Bottle program. This genius concept lets guests try high-end, hard-to-find bottles at cost. “If we pay $80 for a bottle, we pour it out by the ounce at that exact price,” Harol explains. “It’s about making rare, quality spirits accessible—and giving people a chance to taste something special.”
From bold bourbon-forward cocktails like the Young Buck—made with bourbon, ginger, lemon and tobacco bitters that leave a lasting impression—to more indulgent options like the Dutch Uncle, a clarified punch with butternut squash that drinks like a boozy milkshake, the drink menu at Nightingale is anything but ordinary.
“We want it to feel communal,” Harol says. “A place where people can come for a big night out or just sit at the bar, order a drink and feel like they belong.”
And that vibe isn’t slowing down anytime soon. Nightingale just wrapped up what Harol calls “bar upgrade 2.0,” a rooftop escape that now boasts an extended bar with more seating and the crown jewel: a “garden bar,” where guests can handpick their herbal garnishes. Imagine ordering a margarita and watching your server snip a fresh mint sprig right before muddling it into your drink. Those little touches—the ones you didn’t know you needed—give a place its magic.
As the night wore on and the rooftop buzzed with conversation and clinking glasses, it was clear that Nightingale had tapped into something special. It’s more than a bar—it’s a love letter to Holly Springs’ future, a place that says you don’t have to leave town to find a night worth remembering. A place that Harol admires so much that he told us, “I’ll probably grow old and die in this town.” And that says a lot!
So if you’re looking for a rooftop escape with inventive cocktails, rare spirits and a touch of big-city flair, Nightingale is calling. Just make sure you snag a reservation—those prime sunset seats don’t stay empty for long.
Looking for more rooftop restaurants and bars?
AVA Rooftop Bar | 301 Fenton Gateway Drive, Cary | avarooftopbar.com
Perched atop Cary’s vibrant Fenton development, AVA Rooftop Bar is an outdoor oasis featuring a chic, modern design with comfortable seating areas that invite relaxation and conversation. Guests can indulge in Mediterranean-inspired small plates and a curated selection of craft cocktails and wines. Signature drinks like the AVA Margarita, crafted with Hornitos Reposado tequila, blood orange, agave and lime highlight the menu. Regular events, including live DJ performances, add to the lively atmosphere, making AVA a go-to destination for intimate evenings.
Dram & Draught | 3 Fenton Main Street, Cary | dramanddraught.com/location/cary
Also found in Fenton, Dram & Draught caters to whiskey enthusiasts and cocktail lovers alike. The bar boasts an extensive whiskey list and a selection of craft cocktails that showcase creative mixology. Seasonal menus introduce innovative drinks, like this summer’s colorful Rhu-Bliss, a Camelot Mead with génépy, strawberry, lemon, rhubarb, Angostura bitters and soda. A selection of spirit-free cocktails are also available. The welcoming ambiance and knowledgeable staff make Dram & Draught a prime spot for social gatherings.
TapStation | 320 S. Salem Street, Apex | tapstationapex.com
TapStation, situated in the heart of Apex, offers a unique blend of industrial charm and modern comfort. The rooftop area provides an inviting space to enjoy a diverse selection of craft beers and bourbon. The beer menu features a rotating lineup of local brews—including creations made on-site or at their other brewery, Mason Jar—such as the Back Seat Driver Hazy IPA. Grab a pint to go with their Pimento Cheese Egg Rolls. With its relaxed atmosphere and friendly service, TapStation is an ideal spot for unwinding with friends or enjoying a laid‑back evening under the stars.
