Fredericksburg, Virginia, Wins G&G’s “Best Main Street in the South” Bracket

There’s something in the air of this friendly mountain thoroughfare. It’s the kind of place where you can linger all day, chatting up strangers and browsing for treasures at gift shops, sweet shops, gem shops (of course!), and food markets. There’s an incredible playground if you have kids in tow, plus copious benches for coffee and ice cream breaks. If you’re after a bigger meal, pop into the Speckled Trout for Appalachian fare such as cracker-crusted mountain trout with a side of smoked Gouda grits and a North Carolina IPA.

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).

About an hour outside Washington, D.C., Caroline Street is a step back in time to when streets were designed with the community in mind. Depending on when you visit, you’re likely to stumble upon a parade, a festival, a farmers’ market packed with locals, or some history buffs scoping out George Washington’s birthplace. You won’t find chain stores, just independently owned restaurants and shops such as Riverby Books, where you can leaf through used and rare titles. Once you’ve found your next read, pop next door to Sammy T’s, a corner pub in an early-1800s building that once served as an auction house and the town’s post office.

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.

As you stroll Thomasville’s Victorian postcard of a main street, look down at the century-old bricks underfoot; for sixty years whole sections were covered by asphalt before city leaders thought to uncover them in 2015. Among the many worthy shops you’ll pass are Kevin’s Fine Outdoor Gear & Apparel, a long-standing sporting goods store, and the retail outpost of Sweet Grass Dairy, whose artisan cheeses are beloved the South over. Snack on a cheese board featuring house-made pickles and blackberry preserves, or seek out a heartier meal at downtown go-to Jonah’s Fish & Grits.

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. 

Housed in tidy redbrick buildings that date back to 1799, the locally owned businesses along this stretch feel like an Americana throwback. Fuel up with fresh pastries and coffee at Franklin Bakehouse before losing yourself in standout shops. Musician Holly Williams’s boutique, White’s Mercantile, is a favorite for its thoughtfully curated selection of Southern goods for the home. And Landmark Booksellers is a bibliophile’s dream, with more than 35,000 new, rare, and signed books tucked into the shelves of the circa-1800s storefront. 

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.