Come for the tradition, but fall in love with the Holy City's never-ending surprises.

By Tracey Minkin
December 11, 2018
Chris M. Rogers

Christmas in Charleston, South Carolina, is like one big Advent calendar.

This holiday epiphany first arrives while I watch Brianna Berry craft a drink called Smoke & Mirrors, a cocktail of cold-brew coffee, tequila, chile and spiced pear liqueurs, black walnut bitters, and an Earl Grey simple syrup made from tea grown on a South Carolina barrier island. She sets a thick stick of cinnamon burning and caps a snifter over it, setting loose that classic holiday scent into the empty vessel and then filling it with the dark, spicy blend of spirits.

Chris M. Rogers

I'm having lunch in the city's quiet Westside neighborhood at a cozy restaurant called Harold's Cabin, tucking into a plate of wild boar meatloaf and a groaning board of roasted mushrooms, beets, and winter squash, not to mention this cocktail. The winter sun beaming through broad plate glass windows lights up the art-dotted plank walls. It's as cheery in here as the interiors of miniature log cabins that glow along the hillsides of train sets. It's nothing like I imagined Christmas in Charleston to be, but it's exactly what Christmas in Charleston turns out to be.

And that's where the idea of an Advent calendar comes in. Charleston is so famous, so historic, so classic, that the promise of the holidays here is like an idealized scene on the facade of a cardboard Advent calendar. I discover that scene while wandering the streets of the lower peninsula: wreaths dotting grand doors, garlands of magnolia and pine draping wrought iron fences, trees winking from between plantation shutters.

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The palmettos that line King Street—the city's grand parade of stores, restaurants, and bars—are wrapped in twinkling lights, while the shop windows sing with festive holiday displays. In the poinsettia- and Christmas tree-bedecked lobby of the Belmond Charleston Place hotel, a model train makes the slow trek through its own dreamy winter landscape, performing its careful loops for the throngs of children and their parents who visit the display every year as a special holiday ritual.

But it's during lunch at Harold's that I pry open the first little perforated door on my calendar and delight at the surprise within. I keep prying and peering. Lured by the opulence of the window displays at Croghan's Jewel Box (where many Charleston families select a keepsake ornament every year), I realize that the near-life-size Santa Claus figure in the window is done up in a white top hat and a red velvet suit—more dance hall than North Pole—and he's flanked by two reindeer in bustiers and short, flouncy skirts—more Moulin Rouge than The Night Before Christmas. It's saucy and fun. I stand transfixed on the busy sidewalk, watching the reindeer twirl with their knees hoisted high in a perpetual cancan.

Chris M. Rogers

I wander next into a boutique called Worthwhile, where I discover tabletop trees decked with ornaments crafted in the high-gloss style of German glass figural designs of the 1950s—pinecones, acorns, clusters of grapes—but these are irreverent and contemporary in their subject matter: slices of pizza, grapefruit halves, martini glasses. In other shops they might be predictable and even kitschy, but these are elevated and gorgeous. Below, a forest of bottle brush trees, just a few inches tall and in the colors of PEZ candies, creates a crazy blanket of bristly delight. I love classic Charleston, but I love this side of the city even more.

More Advents, more finds. I become a habitué of the lobby of my own hotel, The Dewberry, a converted mid-century Federal office building with a design so contrary to the Georgian architectural glories that dominate locally—I feel like I'm having an aesthetic affair of sorts. I sip a glass of the hotel chef's mother's recipe for boozy eggnog while I ogle the vintage Scandinavian furniture all around me.

Chris M. Rogers

I venture out again to eat, drink, and be merry: I sip a Hawaii-worthy mai tai at South Seas Oasis, a tiny tiki lounge that's hidden down a cobblestone alley. I polish off a plate of pulled pork, spare ribs, and mac and cheese at Rodney Scott's BBQ's outdoor picnic tables—an act with no holiday ties but one that should be on everyone's wish list.

I pick up bottles of small-batch sorghum whiskey and botanical gin (Merry Christmas to me!) from High Wire Distilling Co., a boutique distillery and tasting room on the upper reaches of King Street. And one sweetly quiet night, I spend hours in the cozy corner of chef Jill Mathias' Chez Nous, a European consort to the rustic Harold's, taking my time with veal crudo, handmade pastas, and a fig-and-butterscotch budino, all the while admiring the care with which the nightly menu has been handwritten on card stock.

As a long weekend winds to a close, I wish I could stay here for the entire month of December—I'd catch the Holiday Parade of Boats in Charleston Harbor and drive through the 3-mile incandescent riot that is the Holiday Festival of Lights in James Island. I'd join the high-spirited progressive dinners at the storied Circa 1886 and Wentworth Mansion and tour every historic home. I'd groove with the locals who fill the Charleston Music Hall for the annual Holiday Swing jazz concert and marvel at Ann Caldwell & the Magnolia Singers at the Spirituals at Drayton Hall performances.

And I'd sit rapt in the hard pews of The Citadel's Summerall Chapel—having been escorted to my seat by a fresh-shaved cadet in uniform—feeling the brass and reeds of The Citadel Regimental Band and Pipes wash over me in hymns and traditional songs of the season. And I'd wonder, after the concert, what little door I'd pry open next.

5 Places to Shop in Charleston During the Holidays


This special pop-up in Marion Square spans three weekends in December and has serious riches, which change each year. Be on the lookout for Grit & Grace oyster-shell ornaments, Barbara's Sweetgrass Baskets, and Carolina Millinery Company's handmade hats.


Classic and resplendent, this landmark shop is the spot for an annual Charleston ornament as well as a treasure trove of new and estate jewelry.

Chris M. Rogers


The cheeky Christmas ornaments at Worthwhile are irresistible, and the urban-chic fashions are one of a kind.


A wonderful spot for housewares and art, this commodious shop is also an inspiration stop for lighting, furniture, and design.


The retro-fabulous chocolate holiday figures at Christophe Artisan Chocolatier-Pâtissier are nearly too beautiful to give away (much less devour), but they're worth suffering over. So are the assortments of truffles and hand-painted chocolates.

Chris M. Rogers



You won't look at an office building the same way after staying at this boutique hotel that occupies the circa-1964 L. Mendel Rivers Federal Building and overlooks Marion Square. The Dewberry's interiors are sumptuous, the Living Room lobby is one of the buzziest spots to hang out in the city, and the guest rooms (featuring custom Stickley armoires and seasonally rotating in-room cocktail bars) are urbane nests. Rates from $265.