Savannah, Georgia, USA bars and restaurants on River Street.

8 Oldest Founded Towns To Visit In the Mid-South

The towns that first took root in the MidSouth were strategically positioned along vital waterways, serving as major trade hubs that fueled the growth of the American economy. These original settlements blossomed into some of the most significant locations in the United States, etching their mark on history through key events like the Revolutionary War and the Civil War and tales of ancient ancestors along the mighty Mississippi River.

The MidSouth region is a living testament to the nation's heritage, offering an array of historical landmarks such as Colonial Williamsburg, and providing access to the important waterways surrounding the Mississippi River. More than just a glimpse into the past, these oldest-founded towns are brimming with a vibrant culture that emerged as generations of people made these places their homes.

Whether you're a history enthusiast or simply curious about America's rich past, visiting some of the oldest-founded towns in the MidSouth promises an authentic and inspiring American experience. Explore, learn, and connect with the nation's roots in these iconic locales.

Long Weekend VacationsChoose your ideal destination for a 3-day weekend in the Mid-South.

Williamsburg, Virginia

WILLIAMSBURG, VA - August 17, 2010: An actor playing Benedict Arnold, with crowd in attendance, at Colonial Williamsburg in Virginia.
WILLIAMSBURG, VA - August 17, 2010: An actor playing Benedict Arnold, with crowd in attendance, at Colonial Williamsburg in Virginia. Editorial Credit: Michael Gordon via Shutterstock.

The first settlement in Virginia was in Williamsburg, which was once known as Jamestown and was founded in 1607. The city was renamed Williamsburg after a prisoner started a fire in 1698, and the government stepped in, therefore naming it after William, King of England. It did not completely lose its namesake, as Jamestown is now known as a National Park at the same location. A popular location for history buffs, Williamsburg is home to historical landmarks such as Colonial Williamsburg, where there is a living history museum where actors live colonial life in the streets, workshops, and shops and diverse outdoor landscapes such as historic Jamestown. Visit the Jamestown Settlement and step into American ancestors' methods and farming ways on this exciting trip to one of the oldest-founded towns in the Mid-South.

Annapolis, Maryland

Annapolis, MD, USA 05-02-2021: Street view of Annapolis, Maryland with people walking in historic town and people dining outdoor sitting on tables put on street by local restaurants.
Annapolis, MD, USA 05-02-2021: Street view of Annapolis, Maryland, with people walking in the historic town and people dining outdoors. Editorial Credit: grandbrothers Via Shutterstock.

Annapolis, Maryland, was founded in 1649 and is the oldest town in Maryland. Often called the Athens of America, Annapolis was a tourist hot spot from the beginning. The European style layout harkens back to Queen Anne, who the city is named after, and the roots of the British Empire are encrusted in the city's architecture. Check out the European cobblestones and architecture that promotes authority in this old-found town while walking through Fort Henry. Located on the Chesapeake Bay, the city of Annapolis is worth visiting for anyone seeking an exciting and historical adventure mixed with some thrilling outdoor experiences, such as the Ocean City Boardwalk. Eat some seafood by the water and head across town to enjoy museums that are some of the oldest historical locations in all of the United States. 

Charleston, South Carolina

Charleston, South Carolina, USA cityscape in the historic French Quarter at twilight.
Charleston, South Carolina, USA cityscape in the historic French Quarter at twilight. 

Charleston, South Carolina, was founded in 1670 and is home to some of America’s most important histories as the place where the first ‘official’ gunshot of the Civil War was fired. Visit the maritime environment of Charleston and check out the location of the first-ever submarine attack or take an afternoon enjoying the historical sites that have been kept in the same condition since the times of the Civil War. The oldest-founded town in South Carolina, Charlestown is one of the most important places to visit in the Mid-Southern United States. Visit Joe Riley Waterfront Park, Fort Sumter, or Rainbow Row. Check out the history by stepping on the land where it all began and visit the charming city of Charleston, South Carolina.

Philadelphia, Pennsylvania

Independence Hall in Philadelphia, Pennsylvania.
Independence Hall in Philadelphia, Pennsylvania.

Philadelphia was founded in 1681 and still holds a special value for its historical, cultural, and geographical diversity. Given its location on the Delaware River, Philadelphia became an epicenter for trade and transportation. The terminal of Reading R.R.Co, which may be remembered from the game Monopoly, was popular for moving coal by the sea. In 1809, the first railroad track was laid down in a yard in Philadelphia, and the history of railroads and steamboat travel has been maintained in this oldest-founded town in Pennsylvania. The city has maintained its love of transportation and provides a number of districts for visitors to explore. Visit Reading Terminal Market, the Freedom Bell, and the American Revolution Museum and get moving into Pennsylvania to visit the busiest, oldest-founded town in Pennsylvania.

Bath, North Carolina

Bath, North Carolina - April 25, 2016: Burial ground and c. 1774 Palmer-Marsh House, one of the oldest dwelling residences in the State, with its unique double chimneys on the south front.
Bath, North Carolina - April 25, 2016: Burial ground and c. 1774 Palmer-Marsh House, one of the oldest dwelling residences in the State, with its unique double chimneys on the south front. Editorial Credit: Lee Snider Photo Images via Shutterstock.

The city of Bath was founded in North Carolina by French Protestants in 1705 under great controversy from the Tuscarora Indians who suffered under their reign. Bath is located 50 miles from the Atlantic Ocean, and the French believed the location to be an opportunity for abundance but did not anticipate the arrival of pirates or the four-year war with the Tuscarora Indians, which brought terrible bloodshed to the town. A historical location and charming town in North Carolina, Bath has charming boutiques, exciting outdoor adventures, and captivating history, arts, and entertainment such as the Palmer Marsh House, Historic Bath, and Goose Creek State Park. Bath, North Carolina a prime location for anyone looking to step into one of the oldest-founded towns in the Mid-South.

Natchez, Mississippi

Natchez, USA – December 2, 2022 - View of the historic Natchez Main Street with Convention Center, 19th century buildings, parked cars and Christmas decorations, Adams County, Mississippi.
Natchez, USA – December 2, 2022 - View of the historic Natchez Main Street with Convention Center, 19th-century buildings, parked cars, and Christmas decorations, Adams County, Mississippi. Editorial Credit: Nina Alizada via Shutterstock

Natchez, founded in 1916, is the oldest city on the Mississippi River and became known as a significant slave-trading hub in the Mid-South during that era. Explore the complex history of the Natchez region by visiting nearby cotton and sugarcane plantations, which reveal the difficult legacy of slave labor. The preserved architecture at Stanton Hall, Rosalie Mansion and Gardens, and Choctaw Hall paints a vivid picture of the diverse and divided society of the time. As you walk through these sites, gain insight into the hard work that shaped the surrounding lands and reflect on the impact of the Civil War. A visit to Natchez provides an opportunity to commemorate the lives and experiences of the people who lived and worked along the Mississippi, offering a deeper understanding of this essential part of American history.

Savannah, Georgia

Savannah, Georgia, USA historic downtown sidewalks and rowhouses.
Savannah, Georgia, USA, historic downtown sidewalks and rowhouses.

Savannah, Georgia, founded in 1733, represents a significant development in American urban planning. Before Savannah's establishment, the area was mainly dotted with small forts or settlements. The city's creation was a deliberate effort by the people of Georgia, and it has become known as America's first planned city. This design reflects a collective vision that brought together various elements to create the beautiful and cohesive Savannah we know today, with its grid of charming shops along the streets, vibrant entertainment in buildings, peaceful recreation in parks, and lively dancing at meeting places. Visitors can explore iconic sites such as Forsyth Park, the historic quarter of Savannah, and the Wormsloe Historic Site. Capturing the essence of the American South, Savannah is one of the oldest-founded towns in the United States and is certainly a destination worth visiting.

Shepherdstown, West Virginia

Shepherdstown, West Virginia, USA - September, 15, 2019: German musical band wearing traditional bavarian costumes preparing to Oktoberfest performance.
Shepherdstown, West Virginia, USA - September 15, 2019: German musical band wearing traditional Bavarian costumes preparing for Oktoberfest performance. Editorial Credit: Evgenia Parajanian via Shutterstock.

Dating back to 1734, Shepherdstown is the oldest town in West Virginia. Historically, it is famous for James Rumsey’s invention of the steamboat, but the first settlers who were of German descent highly influenced the culture of the area. The main street, appropriately named German Street, is a great place to grab a drink and enjoy the historical architecture that has been restored to its natural aesthetic over time. Step into history at the home of Antietam Battlefield, one of the worst bloodsheds experienced during the Civil War, or head over to Harpers Ferry, a location made famous for the natural seashore experience and epic views of cliffs hanging over crashing waves. Shepherdstown is one of the oldest-founded towns in the Mid-South and offers visitors plenty of history steeped in culture, modernized into a vibrant and charming area for visitors.

Final Thoughts: A Journey Through America's Historic Heartland

The oldest-founded towns in the Mid-South serve as living testaments to the evolution of the American dream. Rich with history and culture, these towns offer more than just picturesque landscapes; they provide an engaging journey through the critical stages of America's development. Visitors to the Mid-South can walk in the footsteps of their ancestors, discovering the layered histories and cultural landmarks that have shaped the nation. From exploring ancient trails to absorbing the stories embedded in the soil, a trip to these historic towns offers a unique and enlightening experience.

A Journey Through the Mid-SouthDiscover eleven charming cities in the Mid-South
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Brenna Tomas August 2 2023 in Places

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