Vote Now: What’s the Best Main Street in the South?

You’ll know you’ve arrived at Waynesville’s Main Street when you see the iconic steel arch adorning this “Gateway to the Great Smoky Mountains.” Before you hit the trails of those stunning peaks, stop by Mast General Store for new hiking boots (or candy, cast iron, and holiday decor), or duck into galleries, antique shops, and breweries. Local tip: Start the day with biscuits and gravy at the nostalgic Waynesville Main Street Diner, and for lunch, grab a loaded hot dog and Cheerwine at 828 Market before browsing the shelves of N.C.-made goods.

Running through the heart of the oldest town in West Virginia, German Street’s two-hundred-year-old buildings have been thoughtfully repurposed into shops and eateries. The brightly colored storefronts feel bohemian in the best way, and the communal spirit shows on bookshelves spotlighting local authors at Four Seasons Books and the local artist gallery at Lost Dog Coffee. Fall is an especially cheerful time for a stroll, as the leaves turn a bold yellow and orange and warm loaves beckon from Shepherdstown Sweet Shop Bakery (the scratch-made artisan breads are served at restaurants throughout the mid-Atlantic).

Eureka Springs’s Main Street captures both the local topography and the town’s eclectic spirit. Start your day at the basement-level Mud Street Cafe—the impressive coffee selection can fuel you up the Ozark hills as you embrace funky mountain-town vibes at Magpie, a family-run gift shop, and Packrat’s Paradise, a mainstay that’s exactly what you’d imagine it to be. Rest your legs on the deck at Local Flavor Cafe, where the chef is a seventh-generation Eurekan, or in the shade of Basin Spring Park, home to the natural spring that launched this Victorian-era resort community.

There are annual parades and then there’s Middleburg’s Christmas parade, which might be the country’s best. Beyond the expected floats, bands, and marching community members, you’re treated to over one hundred horses and hounds, a nod to the area’s equestrian and hunting traditions. No matter the time of year, shop like a local at Chloe’s of Middleburg (for clothing and shoes curated by a former Bergdorf Goodman buyer) and Crème de la Crème (for glassware, candles, and other home goods). Cap off the day with bar snacks and craft cocktails at the pub at the Red Fox Inn & Tavern, which has been operating since the 1700s.

The social epicenter of this stunning bayfront town, Fairhope Avenue’s laid-back “hey, ya’ll” atmosphere makes it hard to tell a local from a visitor. But the former start their day with biscuits and gravy at Julwin’s and will likely tell you to check out the Fairhope Store for unique gifts and Dr. Music for vinyl (both just off of the main drag). As evening falls, make your way to the bay for a spectacular sunset. Bonus points if you bring homemade gelato from local institution Fairhope Chocolate and Bakery.

With its moss-draped oaks, classical architecture, and historic landmarks, Beaufort’s main drag feels as though it’s frozen in time. That doesn’t mean the shopping isn’t great. Dozens of charming stores—filled with home goods, bins of sweets, antiques, and old-school toys—line the walkable stretch that runs parallel to the Beaufort River. Highlights include Bay Street Outfitters for fishing gear and apparel and Rhett Gallery for local art. Insiders know to grab a loaf of fresh sourdough and beverages from Sweetgrass Pantry & Provisions, then wander over to the waterfront to watch the sun set. 

Paducah is known for its craft and folk art scene, and this twenty-block promenade is its creative community hub. Stretching to the Ohio riverfront, Broadway has all the stops you’d expect in a great downtown street—gift shops with Kentucky-made goods, bakeries and breweries, an antique mall packed with treasures—along with gorgeous nineteenth-century architecture. Check out PAPA Gallery (the Paducah Area Painters Alliance) and Raven & Moth, an eclectic shop where you can pick up a moss-covered birdhouse or artisan jewelry.

Grapevine, situated just twenty-five minutes outside Dallas, is known as the Christmas Capital of Texas, but its main corridor brings the charm year-round. (The vintage train chugging through town doesn’t hurt.) Stop by Good Things for All Seasons for all of your holiday decor needs, check out the wares at Vetro Glassblowing Studio & Fine Art Gallery, and when you’ve worked up an appetite, hit the communal tables at Harvest Hall, which houses eight chef pop-ups, from Mexican street food to hot chicken to craft coffee and cocktails.