Middleburg. Virginia in the mid south

14 Prettiest Towns In the Mid-South

The Mid-South is as diverse and charming as it is historic and under-explored. Writing off the Middle-Southern States of America by throwing them into a stereotype is a mistake: real travelers know of the gems in the Mid-South and where to find them. To make the research easier, we compiled this list of the prettiest towns in the Mid-South. On this list, find charming downtowns, lush forests, bustling communities, wide waterscapes, and a real sense of authentic Mid-South. 

Eureka Springs, Arkansas

Historic downtown Eureka Springs, AR, with boutique shops and famous buildings, via Rachael Martin / Shutterstock.com
Historic downtown Eureka Springs, AR, with boutique shops and famous buildings, via Rachael Martin / Shutterstock.com

Eureka Springs is tucked into the Ozark Mountains of Northwest Arkansas, encompassed by beautifully forested hills and accented by trees and natural hot springs dotted between Black Bass Lake and Lake Leatherwood City Park. The real beauty of Eureka Springs is in its historic Victorian downtown core: Main and Spring Street are lined with cobblestones and shaded on both sides by tall buildings of old Victorian charm like the 119-year-old Basin Park Hotel. For a taste of new Arkansas, visit the Thorncrown Chapel, one of the most unique and enchanting buildings of its kind in the world with a total of 425 windows nested within lush greenery and ample natural sunlight.

Paducah, Kentucky

Paducah, Kentucky: Row of colorful, historic buildings on the main street in the downtown area. Editorial Credit: Angela N Perryman via Shutterstock.
Paducah, Kentucky: Row of colorful, historic buildings on the main street in the downtown area. Editorial Credit: Angela N Perryman via Shutterstock.

In 2013, Paducah was named a City of Crafts and Folk Art by UNESCO. The reason: quilts. Paducah is the home of great quilt making, donning its name "The Quilt City." Of course, it houses The National Quilt Museum and the biggest quilt celebration in the country, QuiltWeek Paducah. 

But Paducah is not just quilts. The largest town in the Jackson Purchase region has twenty blocks of downtown buildings listed as historic districts making for quaint restaurants and shops, including the popular Purple Toad Winery and the Freight House restaurant, serving traditional Southern flavours. After a memorable dinner take the Paducah Riverwalk along the Ohio River. Or, take a trip to Illinois by crossing the Irvin. S. Cobb Bridge.

Berlin, Maryland

Historic Warrenton Virginia, Fauquier County. Old brick buildings and narrow streets. Small souvenir shops for tourists, via Kosoff / Shutterstock.com
Historic Warrenton Virginia, Fauquier County. Old brick buildings and narrow streets. Small souvenir shops for tourists, via Kosoff / Shutterstock.com

Berlin is only 10 minutes from Maryland's famous Ocean City, but still remains largely untouched by flocking summer tourists. Main Street in Berlin is all-brick, reflecting a typical Maryland style but conversely coming to life for a vibrant evening scene of small shops and restaurants. Blacksmith is a fan-favourite dinner spot and is commonly coupled with a pint at Burley Oak Brewing Company. Grab a morning coffee from On What Grounds? cafe and check out the varied artistic scene in Berlin, including The Dusty Lamb for modern work, Beach Memories for glass designs, Henry Fine Arts Collection for traditional art, and the always-entertaining working gallery of the Wooden Octopus, featuring four artists in action. 

Middleburg, Virginia

Central street through Middleburg, Virginia, via Nigel Jarvis / Shutterstock.com
Central street through Middleburg, Virginia, via Nigel Jarvis / Shutterstock.com

Middleburg is "the Nation's Horse and Hunt Capital." This is the quintessential small town: brick-ladden streets, top-quality, reasonably-priced restaurants like the Thaiverse and the Red Horse Tavern, small boutiques, and two Forbes 5-star inns — Red Fox Inn & Tavern, established in 1728 and now one of the oldest inns in America, and the Salamander Resort & Spa that features its own equestrian center. The surrounding area is quiet and scenic, holding fantastic wineries like the massive family-owned Stone Tower Winery and breweries like Lost Barrel Brewing. After a drink, check out the world-class equestrian around Loudoun County: the same area where Olympic riders live and train. Watch a professional jumper show at an equestrian event facility or try out your own horseback ride. 

Natchez, Mississippi

View of the historic Natchez Main Street with Convention Center in Natchez, Mississippi.
View of the historic Natchez Main Street with Convention Center in Natchez, Mississippi. 

Natchez is recognized as a real taste of "Old South." Natchez's location along the Mississippi River delivered economic prosperity to the town and wealthy families who established famous antebellum mansions like the Melrose Estate and the Longwood mansion, both extremely prominent responses of wealth in the mid-19th century American South, highlighted with massive bright white columns and epic symmetrical designs. Continue on your historical study of the South and visit Stanton Hall, the Rosalie Mansion and Gardens, Choctaw Hall, and the Monmouth Historic Inn and Gardens. Then take an epic road trip; Natchez is the starting point of the Natchez Trace Byway that extends through 3 states across 444-miles and many towns, small and large. 

Jonesborough, Tennessee

Overlooking Tennessee's oldest town, Jonesborough.
Overlooking Tennessee's oldest town, Jonesborough.

Jonesborough is Tennessee's oldest town and the self-proclaimed "Storytelling Capital of the World." Likewise, Jonesborough is home to one of the Top 100 Events in North America as described by the Los Angeles Times: the National Storytelling Festival. Jonesborough also holds rich architectural character that offers a look into 1779, its founding year, including Main Street storefronts with brick facades of Federal and Greek Revival style. There are a number of favorite Jonesborough eats, including the Black Olive Italian restaurant, Depot Street Brewing's India Pale Ale and hot dogs, and the Old Town Dairy Bar's simple, classic small-town vibe. For fresh air, locals visit Willows Springs Park to catch views of forested mountains and small, calm lakes.

Black Mountain, North Carolina

Lake Tomahawk in Black Mountain, North Carolina.
Lake Tomahawk in Black Mountain, North Carolina. 

Black Mountain is a quintessential small town perched in the Blue Ridge Mountains, featuring easy access to incredible outdoor activities in the forested mountain range and the nearby Pisgah National Forest. Real explorers should trek the hiking trails in nearby Montreat, including Graybeard Trail, a 9.2-mile (14.8km) uphill trek of difficult terrain with a mountain-view payoff at Walker's Knob. For an easier stroll, visit the family-friendly Lake Tomahawk. Then explore the unique contemporary arts scene in Black Mountain: the Black Mountain Center for the Arts is the center of public art activity, and the Seven Sisters Gallery is recommended by locals for top-quality local art. 

Oxford, Mississippi

The Oxford, Mississippi town hall sits prominently on the town’s historic square, via James Kirkikis / Shutterstock.com
The Oxford, Mississippi town hall sits prominently on the town’s historic square, via James Kirkikis / Shutterstock.com

Oxford is a college town, home to the University of Mississippi (or "Ole Miss"), and carries vibrant energy; known as the home to novelist William Faulkner, Oxford is a cultural hub of arts and literature. The Square, the bustling heart of downtown, holds independent bookstores and art galleries and is host to live performances in the evenings, especially in restaurants and bars like the Roosters Blues House and The Library. Art lovers should plan ahead to visit in the spring to see the two-day Double Decker Arts Festival for the best professional and amateur displays in the region.  For a hands-on experience, local arts and crafts are highlighted and taught at the Yoknapatawpha Arts Council, an arts and events center providing an authentic Southern experience. 

Tallulah Falls, Georgia

Tallulah Falls town in Georgia, via https://www.tallulahfallsgeorgia.org/
Tallulah Falls town in Georgia, via Home - Tallulah Falls (tallulahfallsgeorgia.org)

Tallulah Falls is the epitome of a Southern-lush nature town. The population of under 200 people is serviced by a colorful, tutor-board downtown filled with boutiques and small shops like The General Store and cozy food stops like the Tallulah 1882 cafe. The quaint downtown is the perfect accent to the beautiful Tallulah Gorge State Park, starring the two-mile-long and 1,000-foot-deep (304m) Tallulah Gorge. The gorge is covered on either side by thick foliage, turning beautiful red, yellow, and orange colors in the fall, and complemented by rolling waters falling between rocks below. Take the wooden suspension bridge and accompanying staircases to the gorge floor to feel the steam from the Hurricane Falls along the Hurricane Falls Trail, providing multiple views along the 2.25-mile (3.6km) vertical path. 

Bardstown, Kentucky

The Old Talbott Tavern was built in 1779 in Bardstown, Kentucky. Image credit Ryan_hoel via Shutterstock
The Old Talbott Tavern was built in 1779 in Bardstown, Kentucky. Image credit Ryan_hoel via Shutterstock

Bardstown is the second-oldest town in Kentucky and home to hundreds of historic buildings that line the streets of their peaceful downtown. Within a lot of those old buildings is bourbon: Bardstown is the start of the Kentucky Bourbon Trail and the "World Capital" of Kentucky-made whiskey. There are over 15 distilleries in the small town, including the popular Heaven Hill Bourbon Experience, Preservation Distillery, Lux Low Distillers, and the oldest fully operating distillery in Bardstown, Barton 1792. Just outside of the downtown district is the My Old Kentucky Home State Park starring a former plantation home named Federal Hill and only a walk away from a welcoming campground. 

Siloam Springs, Arkansas

Old buildings in the historic district of Siloam Springs, Arkansas. Editorial credit: RaksyBH / Shutterstock.com
Old buildings in the historic district of Siloam Springs, Arkansas. Editorial credit: RaksyBH / Shutterstock.com

Siloam Springs is an outdoor enthusiast's paradise fitted into a charming small town. It has both a classic-style Main Street with brick buildings and local businesses and diverse natural waterscapes and green tree lines. There's a year-round Farmer's Market, and the same vendors and more set-up shops for community gatherings like the spring Dogwood Festival and the Riverside Festival of Lights. Still, the most recognized attraction is the Siloam Springs Kayak Park, where roughriders test the white water rafting sections and families glide down in tubes. Plus, the park is completed with a family swimming area and a climbing boulder. For a more peaceful scene away from the crowds, try the serenity and calm waters of City Lake Park. 

Townsend, Tennessee

Townsend TN- Image Credit RodClementPhotography via Shutterstock
Townsend TN- Image Credit RodClementPhotography via Shutterstock

The Townsend motto: "The Peaceful Side of the Smokies." Townsend is defined by its natural landscape — the majestic Great Smoky Mountains — and all the essentials for great outdoor exploring. Aside from camping, cycling, hiking, and golfing, the running water cutting through the heart of the town, Little River, is one of the most picturesque walking trails in the state. Nearby is Cades Cove, a picturesque valley with an 11-mile (18km) loop of natural scenery and wildlife. There isn't just nature but also community: a town true to its roots as a lumbering community, it hosts festivals featuring world-class outdoorsmanship, like the Smokey Mountain Woodcarving Festival, or the Great Smokey Mountain Hot Air Balloon Festival. 

Madison, Georgia

Antebellum homes district, Madison.
Antebellum homes district, Madison.

Madison, Georgia is a taste of prime Southern culture. Having prided its rise on education, literature, and philosophy, the town is a symbol of cultural foundations featuring large Greek and Colonial Revival-style buildings with dramatic, symmetric white pews and brick accents: prime examples are the Madison-Morgan Cultural Center and the Madison Welcome Center. Despite impressive architecture, the town still evokes a rural feel: the population is small, the streets aren't cramped, and the Oconee National Forest is only a short drive away. Even closer is the Hard Labor Creek State Park and its biking trails, swimming areas, and serene walkways. 

Beaufort, South Carolina

Front Street in downtown Beaufort, North Carolina. Image credit Stephen B. Goodwin via Shutterstock
Front Street in downtown Beaufort, North Carolina. Image credit Stephen B. Goodwin via Shutterstock

Beaufort is a town on the beautiful Port Royal Island, a coastal paradise: one look at a Beaufort map reveals endless turns of wetland and river that intersect beautifully with classic Antebellum architecture. The town is founded in 1711, making it a cultural landmark with historical buildings like the John Mark Verdier House, the Parish Church of St. Helena, and the Beaufort History Museum. Visitors enjoy the natural scenery on display from the Henry C. Chambers Waterfront Park: a local marina busy with sailing and fishing boats and a background with a deep green treeline, completed with an impressive wooden dock. If the Spanish-moss-draped oak trees look too familiar, don't freak out: the movie Forrest Gump was filmed for a large part in beautiful Beaufort, South Carolina. 

The Mid-South has tradition, charm, and serenity

Plan a trip to the Mid-South for an area to visit an area that has both kept close to its historic roots, as evidenced by its prominent and characteristic architecture and rural feel, and at the same time expanded in the arts, theatre, and outdoor recreation. Travel the Mid-South and try each charm there is to offer: they're not hard to find. 

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