A Historic Walking Tour of Charleston

Walking the streets of Charleston, South Carolina, evokes a sense of nostalgia and an urge to simply unwind. Perhaps its the swaying palm trees, charming colonial architecture, or inviting coffee shops and restaurants- or maybe it is something more. Come along with us on a historic walking tour of Charleston and see for yourself!

A Historic Walking Tour of Charleston

We created this walking tour to help visitors explore some of the most popular and unique sites that Charleston has to offer. Of course, this is far from an all-inclusive list and there are many sites not mentioned here. The best part is, as you wander about the city, you are bound to see so many interesting and captivating buildings, monuments, restaurants, and shops. Thus, you can make this walking tour your own!

The 10 sites on this walking tour are listed below, followed by a map of the recommended route. This will take you through some of the most historic and beautiful parts of the city, so have your camera ready!

1 – Historic Charleston City Market

2 – Powder Magazine

3 – St. Philip’s Church

4 – Philadelphia Alley

5 – Old Slave Mart Museum

6 – St. Michael’s Church

7 – Old Exchange and Provost Dungeon

8 – Rainbow Row

9 – Heyward-Washington House

10 – The Battery

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Stop #1 – Historic Charleston City Market (188 Meeting Street)

Welcome to the historic Charleston City Market! This incredible (partially open-air) market was first erected between 1788 – 1804 and today, stretches four city blocks. It was designed as a public market, where people could buy beef, fish, vegetables, fruits, and all sorts of goods and sundries. The large Greek-Revival style building you see (also in the picture below) is known as Market Hall, which was designed by architect Edward B. White and constructed in the 1840s. The building was repainted the original yellow paint and green ironwork after Hurricane Hugo damaged the building in 1989 (many locals did not like this color scheme- yet it remains).

Today, countless stalls house vendors offering everything from handmade goods (hats, baskets, etc.), souvenirs for the tourist, and locally-sourced food and snacks. You could spend hours meandering the long corridor of City Market and exploring each stall- enjoy!

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Stop #2 – Powder Magazine (79 Cumberland Street)

Charleston’s small powder magazine, which is dwarfed by surrounding buildings today, was once one of the most important structures in the city. It completed in 1713 and used to safely store gunpowder for the city (it was also used during the American Revolution). After 1780, it was no longer used as a magazine and was eventually privately owned. Since then, it was used as a stable, wine cellar, print shop, and even a carriage house. In 1902, it was saved from demolish and purchased by the National Society of the Colonial Dames. A unique structural feature of the magazine are the nine square-brick pillars, which create a stunning series of archways in the interior. This, combined with 35-inch thick walls, was likely to better absorb an internal explosion and avoid a larger accident.

Today, the Powder Magazine serves as a museum, which explores colonial Charleston and the role the magazine played in the city’s history (check out their website for additionally information). Although it is a small building, the staff is incredibly friendly and there are some neat exhibits to check out. Oh, and they are dog-friendly!

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Stop #3 – St. Philip’s Church (142 Church Street)

St. Philip’s Church was founded in 1680 and is the oldest congregation in the United States south of Virginia. The current church building was completed in 1836, after the 1723 building burned down. Other than its beautiful steeple and storied congregation, the church is best known for the famous individuals buried within its churchyard. This includes Edward Rutledge (a signer of the Declaration of Independence) and Charles Pinckney (a signer of the United States Constitution), just to name a few.

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Stop #4 – Philadelphia Alley

One of the more interesting spots in Charleston is Philadelphia Alley, which is a beautiful pedestrian walkway that spans one block, between Queen Street and Cumberland Street. While today it is a peaceful walkway sought out by curious visitors, it was once a more secluded passageway used by locals and possibly thieves and men defending their honor through duels (one nickname it has earned is “Dueler’s Alley”). In fact, some say minor damage and chips in the brick wall is from errant bullets!

The alley received its current name after the city of Philadelphia, which sent funds to help rebuild the alleyway and surrounding buildings after a fire destroyed it in 1810. If you want a particularly frightful experience, wander down Philadelphia Alley at night- many say that it is haunted by the many spirits from Charleston’s past.

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Stop #5 – Old Slave Mart Museum (6 Chalmers Street)

One of the most enriching and sobering sites we visited was the Old Slave Mart Museum, which has operated intermittently since 1938 and is the first African-American slave museum. On display are multiple exhibits that tell the sorrowful story of slavery and Charleston- both of which are forever intertwined. Most visitors to Charleston do not realize that Charleston’s financial success was built upon the slave trade and at one point, 35-40% of all slaves coming into the United States came through Charleston. Needless the say, if you want to truly understand the complex history of Charleston, a visit to the Old Slave Mart Museum is a must.

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Stop #6 – St. Michael’s Church (71 Broad Street)

St. Michael’s Church is perhaps the most iconic building in all of Charleston. The cornerstone for St. Michael’s was laid in 1752 and after nearly nine years of construction, the church opened its doors for services in 1761 (interestingly, the architect of the church is unknown). As revolutionary fervor swept over the British colonies throughout the 1760s, St. Michael’s Church served as a steady symbol of the role faith played in many colonist’s lives.

After the Revolutionary War and the establishment of the American Republic under the U.S. Constitution, President George Washington made a southern tour of the states. In May 1791, President Washington visited Charleston to see many of the late war’s battlefields and the city’s landmarks. This included St. Michael’s Church, where Washington worshipped (in pew no. 43) and even climbed up to the top of the steeple, which offered unparalleled views of Charleston and the surrounding landscape.

The church is located at the intersection of Meeting and Broad Streets, known famously as the “Four Corners of Law.” The intersection is so named because each street corner is occupied by a building associated with religion/ecclesiastical law (St. Michael’s Church), local law (Charleston City Hall), state law (Charleston County Courthouse), and federal law (U.S. Post Office and Federal Courthouse). Additionally, buried in its churchyard are Charles Cotesworth Pinckney (a Major General in the Continental Army and signer of the United States Constitution) and John Rutledge (a signer of the United States Constitution). If you wish to visit the church (free of charge), it is open Sunday – Tuesday and Thursday (it is closed Wednesday, Friday, and Saturday).

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Stop #7 – Old Exchange and Provost Dungeon (122 East Bay Street)

The Old Exchange and Provost Dungeon was completed in 1771 as a Custom House for the city of Charleston (then known as Charles Town). The Georgian-Palladian architecture highlighted the wealth and prestige of Charles Town, which proved to be one of the most industrious and diverse cities in the North American Colonies at the time. The palatial building (for 18th-century Charleston, anyways) was used for a variety of functions during its early years: a Custom House, market/exchange, meeting place, and even a gaol (jail). Importantly, the Old Exchange was a primary location for slave auctions throughout the colonial era and 1800s. This horrific enterprise, based on human bondage, was perhaps the most important factor in Charleston’s financial success and growth.

When the British Army occupied Charleston beginning in 1780, the Exchange was used primarily as a prison. In particular, they converted the basement, once used to store merchandise and goods, into a prison or “dungeon.” In this cold, dark space was held American political prisoners, insubordinate British soldiers, citizens, and enslaved African Americans. Some of the most famous prisoners held here were Edward Rutledge & Arthur Middleton (signers of the Declaration of Independence), Christopher Gadsen (Lt. Governor of South Carolina), and Continental officers taken during the Battle of Camden.

The Old Exchange remained, primarily, a British military until 1782. On December 14, 1782, the British Army evacuated Charleston as the war began to wind down and the building was eventually turned over to the people of Charleston. In 1788, the building was used by the South Carolina Constitutional Convention, which debated the groundbreaking document. When President George Washington visited Charleston in 1791 (as part of his southern tour), numerous dinners and events were held in the Exchange. Truly, it was the central gathering place for the city during this time. Unfortunately, the building’s importance waned throughout the 1800s, although it was used as a Federal Post Office for many decades (to include service as a Confederate Post Office during the Civil War).

Thankfully, the building survived the American Civil War and remains to this day as an architectural gem within the city. The Daughters of the American Revolution (DAR) preserve and manage the Old Exchange & Provost Dungeon and it is open to visitors for tours. It is open Monday – Saturday (9AM – 5PM) and Sunday (11AM – 5PM). Pricing and updated details can be found on their website.

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Stop #8 – Rainbow Row (83-107 East Bay Street)

“Rainbow Row” is a series of 13 pastel-colored houses located along scenic East Bay Street. This beautiful backdrop is naturally a favorite spot for tourists, newlyweds, and just about anyone passing by to take pictures. Most of these homes were actually built around the 1740s and were lived in by merchants who capitalized on Charleston’s vibrant maritime commerce and trade (they usually lived on the second floor and ran their business on the ground floor).

“Rainbow Row” as it is known today originated in 1931, when Lionel and Dorothy Porcher Legge purchased the row of houses. Dorothy made the decision to paint the row run-down buildings a shade of pastel pink. Over the years and as each building was purchased by others, the new owners decided to paint their home a different pastel color. Of course, this sparked a unique tradition and created one of the most iconic and beloved spots in all of Charleston! Comically, one legend is that the homes were painted these wild colors to assist drunken sailors find their way home at night; however, there is nothing to corroborate this reasoning.

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Stop #9 – Heyward-Washington House (87 Church Street)

The Heyward-Washington House has been dubbed the city’s “Revolutionary War House.” Built circa 1772, this was once the home of Thomas Heyward Jr., one of South Carolina’s four signers of the Declaration of Independence. It also accommodated President George Washington during his stay in Charleston from May 2-9, 1791 (hence the name).

In 1929, the house was purchased by the Charleston Museum and it opened as the city’s first historic house museum. Today, it remains one of the premier house museums in the city and displays a remarkable collection of elegant 18th-century furnishings. More importantly, they discuss the life and experience of the enslaved people who toiled for the Heyward family and others at this house. Also, be sure to check out the stone “carriage step” out front, which is one of over 100 carriage steps around the city (Cher and Daisy were chilling on it in the picture below).

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Stop #10 – The Battery

“The Battery” refers to the southern tip of the peninsula on which Charleston sits. It is so named because it is historically (specifically, during the American Civil War) a defensive seawall where artillery was placed to defend the city and repel enemy ships. But even by 1838, the eastern side of the battery became a promenade (public walkway), which is still enjoyed by visitors and locals alike.

Today, there are multiple cannon and artillery pieces on display throughout the Battery. This includes four thirteen-inch mortars, which were all used by Union (Federal) troops for the bombardment of Fort Sumter in October 1863. A placard on the ground near these mortars claims that “they may well form the world’s largest collection of this type weapon.” Aside from the amazing weaponry on display, the Battery offers unparalleled views of Charleston Harbor and the surrounding area.