From the pottery capital to an all-American city and "the town that fooled the British" in the War of 1812, St. Michaels, the American South, is brimming with quaintness. Each characterful town evokes a sense of individual quaint charm, from deeply rich history in St. Augustine to thriving art and culture in Staunton and natural scenes like the Virginia Creeper Trail in Damascus.
The South takes you with its quaint hand and a gentle beating heart through time and countries. From Fredericksburg, full of German heritage, to St. Augustine, replete with European sights dating back to the 1500s, there are also the gingerbread Victorians, Federal, and Gothic cottages in Smithfield, the "Ham Town" in Virginia.
Damascus, Virginia

You can enjoy scenic views of the Appalachian Mountains and fun cycling experiences along the right-of-way rail line from the 1880s industrialization of the United States. With its pleasant southern weather and deep historical significance, Damascus is a popular destination for all-level outdoor lovers to take a stretch of the well-traveled route. The internationally praised trail is a beautiful place to bike along the significant landscape where the railroad would creep along the terrain. You can unwind at the top-rated Damascus Brewery and wind down at the reliable Damascus Old Mill Inn!
Most Scenic Towns In The Southern United StatesThe South is well-known for its warm hospitality that comes to life in towns like St. Augustine and Fairhope.
Fredericksburg, Texas

Tucked within the Texas Hill Country, the adorable small town with a rule against chain stores is resplendent to browse for gifts or enjoy window shopping. With a whopping 150 boutiques down the main roadway, it is a real eye candy on a stroll for your soul, with breweries to warm up, or grab a mulled wine on a stroll down the festive main street. Sprouting fully-stocked biergartens in the warmer months, Oktoberfest revs up the whole craft brew scene every year. The state-of-the-art National Museum of the Pacific War is always "in season," while the surrounding Lyndon B. Johnson State and National Historical Parks call for hikes in the pleasant southern weather!
Gatlinburg, Tennessee

The eastern Tennessee town is a real quaint Appalachian haven through every season, like in the budding spring season under the wildflower slopes of Mt. LeConte in all its mountain flora glory. Attracting nature enthusiasts and hiking lovers with great weather, the Great Smoky Mountains National Park, the most visited in the nation, boasts over 150 official hiking trails! You can stay at the popular Appy Lodge with pool slides or at the really cool Zoder's Inn & Suites, overlooking a tumbling roaring fork from its red iron wrought iron balconies!
Georgetown, South Carolina

The South Carolina Lowcountry town with a cute downtown has a more cozy vibe than the more famous neighboring coastal cities. Its Pee Dee River waterfront is strewn with heritage sights, beautiful old homes, and southern charm prevailing through local nooks that will steal your heart! There's the tropically-inspired Eve's Caribbean Soul Food for a totally unique and cozy holiday dinner, just a hop from the must-visit Kaminski House Museum. The mega-popular River Room Restaurant overlooks the historic district on one side, with the South Carolina Maritime Museum and Rice Museum just a stone's throw away and Goat Island with Lafayette Park across the waters!
Marble Falls, Texas

Marble Falls is the perfect base for exploring some of the state's most sought-after landscapes, like the nearby Pace Bend Park for hiking and biking to the town's own Lakeside Park. You can make a day out of swimming and fishing in Lake Marble Falls, with Lake Lyndon B. Johnson to the north and Lake Travis to the south, while Krause Springs's own waters are crystal clear for swimming. From Blue Bonnet Cafe in the morning, you can unwind at Fiesta Winery Marble Falls, with a scenic fountain, and end it at the Real New Orleans Style Restaurant—some of the state's iconic hotspots! WorldMark is a mega-popular resort-style stay with views and family attractions like a water park.
Ponchatoula, Louisiana

Boasting many strawberry-growing farms in the fertile area, the slow-paced town comes alive during the Ponchatoula Strawberry Festival in the spring, when you can taste the best of it through the strawberry harvest! Friendly locals host the Ponchatoula Country Market in the historic train depot with crafts and rare items from the best of the best businesses in the area right here, while Kliebert & Sons Alligator Farm, unlike any other, offers unique animal interactions for a fun family day activity!
Seagrove, North Carolina

With over 100 local potters and shops for one-of-a-kind shopping, the Seagrove Pottery Festival is an event you can't miss. Offering unique creations by the finest ceramic artists in the area, you can view, browse, and buy works to update or decorate your home and stock up on holiday gifts or souvenirs for others. During your stay, The Seagrove Stoneware Inn welcomes you under the exclusive helm of potters, while the nearby cool day trips include the NC Zoo in Asheboro, just 13 miles away, or 40 miles to Greensboro down the road!
Smithfield, Virginia

The locals take great pride in preserving traditions and the natural bounty along the Pagan River that provides fertile soils. The famous ham, a showcase of its culinary heritage, attracts visitors to Smithfield, while the picturesque landscape beckons with outdoor opportunities to enjoy all this scenic beauty. You can experience the best of it over a weekend when you stay waterfront at Smithfield Station and have dinner at The Cockeyed Rooster Cafe, while a Sunday morning stroll through Windsor Castle Park will lead you to the Farmer's Service Company, just north, to stock up!
St. Augustine, Florida

From the battlegrounds of Castillo de San Marcos to the white sands of Ponte Vedra Beach with cerulean waves, the quaintness overwhelms all your senses! You can pop into various establishments overlooking the ocean here in The South’s Best Food Town, according to Southern Living Magazine! From its palm-lined avenues and squares with flowers and fountains, you can take a sail out with St. Augustine Sailing and return for a fantastic meal at sunset. Harry's Seafood, Bar & Grille is incredibly popular with its verdant, vast, and cozy outdoor setting under the year-round pleasant weather!
St. Michaels, Maryland

With roots dating back to 1677, you can explore the meaning behind its proud moniker of "the town that fooled the British" in the War of 1812 and gorge on seafood during the Maryland crab season from April through November. St. Michaels, a quintessential part of Eastern Shore getaway history, festoons your eyes with nautical views from the past and out-of-this-world sunsets! The Victorian downtown is charming on a stroll with historical buildings, local shops, and outfitters—the perfect spot for a girls’ weekend to shop, dine, and relax. You can take the popular sunset cruise to see the magical town and stunning scenery behind you while sipping cocktails on a romantic escape or even a guy-friend getaway!
Staunton, Virginia

Big on southern charm, this classic "small town USA" with a vibrant cultural scene greets you with no agenda of your own and plunges you deep into the culture at the American Shakespeare Center with staged plays in a replica of the Globe Theatre! You can dive into nature at the nearby Shenandoah National Park and find trendy breweries to unwind at or delicious restaurants to dig into fresh culinary creations. There is also the mega-popular Gypsy Hill Park with its Dog Park, while the charming boutique Blackburn Inn offers beautiful rooms to relax in with traditionally excellent hospitality.
Cutest Small Towns In The Southern United StatesFrom the welcoming and charming to the ancient and cultural, each town offers an exclusive experience that sets it apart from the rest.
With many coastal towns in the Southern United States, you can enjoy the best marine views along the Chesapeake Bay in St. Michael's or St. Augustine. The unique cultural experience pulls you in with a sense of wonder and belonging, while the gracious charm and Southern hospitality will only guide you along sightseeing and adventures.
Each town has its own distinct story to tell, like Marble Falls, a unique waterfront town with fine weather, wines, and sights like its 50-foot waterfall on the banks of Lake Marble Falls and its shelf of limestone across the river. Replete with accommodations for all styles, you can have a real quaint vacation or a getaway respite for some express warm-weather R&R.