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Charleston is renowned for its Southern charm. Its lovely buildings are filled with graceful architectural details that conjure images of sipping sweet tea on a piazza on a sultry summer afternoon.

But there is so much more to these buildings – many from the Antebellum era, many designated as National Historic Landmarks – than what you see on the outside. Each one holds a rich history, filled with human stories that need to be heard in order to understand their significance.

Take a walking tour with experts like Charleston Strolls, Bulldog Tours or Two Sisters, who will give you an overview of the city’s rich history and share anecdotes that make that history come alive. Then go back to tour each site individually, ideally with a docent.

Here are ten historical buildings that are so much more than a pretty facade.

Old Slave Mart Museum

Old Slave Mart Museum — Photo courtesy of Charleston Area CVB,

The Old Slave Mart Museum should be your first stop when visiting Charleston.  

Considered the last existing slave auction gallery in South Carolina, this space is sacred ground. It’s where slaves were actually bought and sold, and spending time there is a profound experience. Listen to a real interview with a former slave, read the in-depth information which is powerful and horrifying, and talk to the staff – many of whose family roots can be traced back to slaves.

Charleston is a beautiful city but much of it was built on the backs of slaves, and the Old Slave Mart Museum’s place on the National Register of Historic Places officially acknowledges that history to make sure it’s never forgotten. 

Charleston City Market

Charleston City Market — Photo courtesy of Charleston Area CVB,

Often mistakenly confused with the Old Slave Mart Museum (which has absolutely nothing to do with it), the Charleston City Market is a must-visit. One of the oldest public markets in the country, it houses dozens of booths and shops featuring the works of local artisans, including 50 sweetgrass basket weavers who keep the 18th century tradition alive.

In 1788, Charles Cotesworth Pinckney ceded the land to the City of Charleston with the stipulation that it had to remain in use as a public market for perpetuity. The original buildings were erected in 1804, and today, Charleston City Market is considered the cultural heart of the city and continues to be Charleston’s most visited attraction.

Wentworth Mansion

Suite at Wentworth Mansion — Photo courtesy of Charming Inns

Consistently named one of the best hotels in the country, Wentworth Mansion remains true to its roots as a private residence, making you feel right at home while treating you to five-star luxury.

Francis Silas Rodgers, a wealthy cotton merchant, completed the elegant 24,000-square-foot, four-story home in 1886, and, upon his death, it was described as the finest in the city. It many ways, it still is.

The building retains some of its original architectural features, including custom-built louvered window treatments with original Victorian hardware installed in 1886 and a rooftop cupola with panoramic views of Charleston.

The carriage house has been converted into the award-winning Circa 1886 restaurant, and the stable is now the Spa at Wentworth Mansion because pampering has never gone out of style.

Boone Hall Plantation

Boone Hall Plantation — Photo courtesy of Charleston Area CVB,

As you approach Boone Hall Plantation, be prepared to take photos of the beautiful tree-lined entrance which makes it instantly recognizable.  Boone Hall was founded in 1681 and was opened to the public in 1956 so people could understand what everyday life was like on a plantation.

Take advantage of all the educational opportunities that are included in the price of admission: a coach tour around the entire 738 acres, a house tour of the Georgian-designed mansion, a slave history presentation that gives you a sobering look at their living quarters through eight original cabins, and the live “Exploring the Gullah Culture” presentation, which introduces visitors to the unique culture formed by African slaves.

One of America’s oldest working farms, Boone Hall has been continuously growing and producing crops for more than three centuries. Today, it sells its produce across the street at its own Boone Hall Farms Market.

Heyward-Washington House

Heyward-Washington House — Photo courtesy of Charleston Area CVB,

Charleston’s first historic house museum, the Heyward-Washington House was built in 1772 for Thomas Heyward, Jr., one of four South Carolina signers of the Declaration of Independence, and was opened to the public in 1930. The City of Charleston rented the Georgian style double house for President George Washington during his week-long visit in 1791; hence, its name.

Recognized as a National Historic Landmark, the property features the only 1740s kitchen building in Charleston open to the public, as well as formal gardens featuring plants commonly seen in the Lowcountry in the late 18th century.

The house also holds a significant collection of historic Charleston-made furniture including the gorgeous Holmes-Edward Bookcase, considered one of the finest examples of American-made colonial furniture.

Dock Street Theatre

Dock Street Theatre — Photo courtesy of Charleston Area CVB,

The first building in the country designed exclusively for theatrical performances, the Dock Street Theatre is considered “America’s first theater.” Although it burned down in 1740 and was turned into a hotel for many years (hosting infamous guests including John Wilkes Booth’s father), it was restored for its original purpose by the City of Charleston as a Works Progress Administration project.

The theater originally opened on 1736, with a performance of The Recruiting Officer by George Farquhar, and it reprised that play when it re-opened in 1937. Today, it’s home to some of the city’s finest cultural institutions including Spoleto Festival USA and Moja Arts Festival. Charleston Stage, the theatre company in residence, presents 120 performances each season.

Located in the French Quarter of Charleston, the theater is a top Instagram spot,  particularly the silhouette of the wrought iron balcony against the spire of St. Philip’s Church.

Kahal Kadosh Beth Elohim (KKBE) Synagogue

Kahal Kadosh Beth Elohim Synagogue — Photo courtesy of Kahal Kadosh Beth Elohim Synagogue

The sanctuary at Kahal Kadosh Beth Elohim (which means Holy Congregation House of God) is the second oldest synagogue building in the United States and the oldest in continuous use.

A National Historic Landmark, KKBE was founded in 1749 as a Sephardic Orthodox congregation. In 1840, when the Temple was rebuilt after the great Charleston fire in 1838, progressive members convinced the congregation to install an organ – the first time a synagogue introduced instrumental music into its worship.

Since then, KKBE has been connected with religious reform. Charleston is acknowledged as the birthplace of Reform Judaism in the United States and KKBE’s colonnaded temple, dedicated in early 1841, is renowned as one of the country’s finest examples of Greek Revival architecture.

John Rutledge House Inn

Piazza at John Rutledge House — Photo courtesy of Charming Inns

Charleston’s longest consecutive AAA Four Diamond recipient since 1990, the gracious John Rutledge House Inn is proof that Southern hospitality actually exists.

A National Historic Landmark, the house was built in 1763 by John Rutledge, a prominent South Carolina politician, for his young bride. After he sold it, the United States Courts sat in the second floor drawing room for a while, and drafts of the Constitution were written within its walls.

Later, after the Mayor of Charleston bought the house, President William Howard Taft was a frequent guest and, during this time, butler William Deas invented she-crab soup, a now-signature Charleston dish. 

Middleton Place

Middleton Place — Photo courtesy of Charleston Area CVB,

A National Historic Landmark, Middleton Place is home to America’s oldest landscaped gardens and four generations of the Middleton family, including Arthur Middleton, a signer of the Declaration of Independence.

You can stay at the intimate and secluded Inn, which blends history with modern luxury, then step back in time at the Plantation Stableyard, where costumed artisans demonstrate weaving, blacksmithing and other activities of a self-sustaining 18th century plantation. 

Powder Magazine

Powder Magazine — Photo courtesy of Charleston Area CVB,

South Carolina’s oldest public building stored loose cannon powder for nearly a century, and today this National Historic Landmark is the only standing component of the original fortification that once surrounded Charleston.

In 1902, almost 200 years after it was built, the National Society of the Colonial Dames of America in the State of South Carolina purchased the building, saving it from destruction. In what is believed to have been the city’s first preservation project, the organization restored it and opened it as a museum dedicated to early Charleston history.

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