South's Best Small Towns

You have to tip your hat to a place that considers its municipal pier the “town square.” That’s the charm of this bayside burg, originally founded as a utopian society in the late 19th century. Fairhope’s knack for creative thinking is reflected in the many artists and authors who call it home and the galleries that dominate downtown. beautifulfairhope.com

This great old college town on the edge of the Tennessee River oozes creativity, from hometown heroes W.C. Handy (the father of blues) and legendary record producer Sam Phillips to contemporary designers Billy Reid and Natalie Chanin. Experience the town’s creative vibe during First Friday sidewalk art shows or by perusing renowned galleries such as ARTifacts. Wander through one of Frank Lloyd Wright’s most iconic designs at the Rosenbaum House. Just down the road is Muscle Shoals, home of FAME Studios, where Aretha Franklin recorded “I Never Loved a Man” (her first big hit), Wilson Pickett recorded “Mustang Sally,” and Etta James recorded “Tell Mama.” Today, it’s a magnet for young Southern bands attracted by its storied pedigree. visitflorenceal.com

Stroll the palm-lined Centre Street, which stretches all the way from historic downtown Fernandina to the harbor, and you’ll see what makes this small town on Amelia Island so spectacular: boutiques galore, Le Cordon Bleu-trained chefs, and a watering hole fit for a Norman Rockwell painting (Palace Saloon). Did we mention the beach? www.AmeliaIsland.com 

Good luck finding a more Gone with the Wind town than Madison, which Union General William Tecumseh Sherman spared. (Did he really think it was “too pretty to burn,” or was he just doing a favor for an old West Point classmate? Choose your mythology.) Madison has one of the largest historic districts in the state of Georgia, complete with the requisite antebellum plantations, beautifully restored, and a pedestrian-friendly downtown filled with shops and eateries. madisonga.com  

Five of the country’s most storied bourbon distilleries call Bardstown home, making the small town of 11,240 the “Bourbon Capital of the World.” Sure, you’ll come for the spirits, but you’ll stay for the picturesque town square, lined with antique shops, boutiques, and restaurants dishing up Southern delicacies. visitbardstown.com 

A tiny bayou town just a short hop from Lafayette, Breaux Bridge is not only the “Crawfish Capital of the World,” per the Louisiana legislature, but lays claim to having invented crawfish etouffee. It’s in the heart of Acadian Louisiana, with all the fantastic food and music that entails. Cajun dancers have been two-stepping and waltzing around the beautiful old dance floor at La Poussiere since 1955. On Saturdays, Café des Amis serves a Zydeco breakfast with live music downtown, where we go antiquing and visit locally owned shops.

Natchitoches is the state’s oldest town, settled by the French in 1714. Local historians swear this is where New Orleans got the idea for all that wrought iron in the French Quarter. Judging by the facades along Front Street, which predates the French Quarter, we believe them. The Steel Magnolias tour is a must for fans of the 1989 tearjerker, which was filmed here. natchitoches.com  

Berlin (pronounced BURL-un) is so danged picturesque that Runaway Bride was filmed here, and if it’s good enough for Julia Roberts . . . Historic red-bricked buildings dominate downtown, which is packed to the gills with boutiques and eclectic restaurants. The beach isn’t far, and the town even has its own signature dessert—the peach dumpling. berlinmainstreet.com

Known as the “Pearl of the Chesapeake,” Rock Hall sits directly on the upper eastern shore of the Chesapeake Bay, offering the quintessential Bay experience. Working fishing boats and pleasure cruisers fill the harbor; steamed crab is available everywhere; and you can even watch regattas just beyond the harbor. rockhallmd.com

The food shouldn’t be this good in a town of just 17,000, but you’ll have more than 100 restaurants to choose from, many of which mix the nearby Gulf’s bounty with the town’s French influence (it was founded by the French in 1699). Ocean Springs has one of the prettiest downtowns in the South, with local shops, galleries, and restaurants lining Washington Avenue and Government Street and coastal architecture shaded by towering live oaks—all this plus the Gulf Islands National Seashore and a soaring pedestrian bridge crossing the bay into Biloxi. oceanspringschamber.com

William Faulkner’s serene and stately home, Rowan Oak, is reason enough to visit, but the turnip greens at Ajax Diner or fried catfish at City Grocery are also worth the trip to Oxford. James Beard-winning chef John Currence has a number of restaurants here. Oxford’s historic Town Square is filled restaurants, bars, galleries, and boutiques. Time your visit to coincide with an Ole Miss home game, and you’ll see tailgating elevated to an art in The Grove. (But you’ll want to book that hotel room several years in advance.) visitoxfordms.com

The architecture in this state capital is stunning, with the capitol building, Supreme Court building, and Governor’s Mansion anchoring the historic downtown (not to mention one of the state’s most historic ice cream parlors). The 240-mile Katy Trail runs through town along the Missouri River, and Missouri’s wine country is just beyond the city limits. downtownjeffersoncity.com 

Highlands is a retreat in every sense of the word. Less than 1,000 people live year-round in this mountain town, which has perfected the art of relaxation, from the plush digs at Old Edwards Inn to the impressive number of fine dining options (we like the innovative Cypress International). Downtown is lined with upscale boutiques and galleries, all of which sit within striking distance of some of North Carolina’s most dramatic peaks and rivers. highlandschamber.org

This 300-year-old coastal town is rich with antebellum architecture, most of which is framed by moss-draped live oaks. But the town isn’t stuck in the past, thanks to a progressive food scene, which has spawned a renewed oyster industry, and an active population that makes the most of the surrounding rivers, islands, and beaches. beaufortsc.org

Downtown Landrum has plenty of small-town charm. Antique shops with brick storefronts fill the center of town, while a restored train depot gives a sense of the town’s past. But you have to explore the surrounding foothills to appreciate the beauty of Landrum. Take a drive through South Carolina’s horse country, cruising through rolling horse pastures hemmed by white farm fences, then hit downtown and refuel at the Hound and Hare. cityoflandrumsc.com 

A saloon/general store and a dance hall—that’s all there is to Luckenbach, and yet the town has become a symbol for Texas cool, thanks to its ties to country music lore and recordings by Willie Nelson, Jerry Jeff Walker, and Waylon Jennings. You can still catch live country music most weekends, and locals contend this is the best dance hall in the entire state (though they might get an argument from the folks in Gruene). luckenbachtexas.com

Situated on a highland desert plain with the Davis Mountains to the north, Big Bend National Park to the south, and the Chisos and Chinati Mountains to the southeast and southwest, respectively, Marfa is West Texas. (The James Dean-Rock Hudson-Elizabeth Taylor classic Giant was shot here.) Maybe it’s the starkly dramatic landscape and huge sky that attract so many creative people. This little town is home to such art installations as the famous Prada Marfa (a fake Prada store), as well as contemporary art at the renowned Chinati Foundation created by artist Donald Judd, and many other galleries. You’ll also find upscale tee-pees for rent and handmade everything, from furniture to cowboy boots. Not bad for a town with a population of just 1,900. visitmarfa.com 

You’ve got the mountains rising from all sides of town, the Blue Ridge Parkway running north and south, and all of the old time, bluegrass music you could ask for. A stop on The Crooked Road, Virginia’s Heritage Music Trail, Floyd takes its farm-centric roots and adds a touch of artistic whimsy. Show up for the Friday Night Jamboree at the Floyd Country Store to see the town at its finest. visitfloydva.com

Horse country rolls away from Middleburg’s tiny downtown, broken only by the occasional Federal-style estate. Eventually, the green pastures give way to the Blue Ridge Mountains on the horizon. This is serious Hunt Country, so expect to see locals fresh off the trail in places like the Red Fox Inn & Tavern (established 1728), the Red Horse Tavern, and Journeymen Saddlers. middleburgonline.com

Shepherdstown has everything you’d expect from a small Southern town—a historic downtown, centuries-old homes converted into B&Bs, and Southern fare made from scratch. But it also has some surprises up its sleeve—like art in spades. You’ll find performances from Shepherdstown’s own theater troupe, galleries brimming with local and regional art, and a vibrant live music scene—everything from street performers to a chamber orchestra. shepherdstown.info