For one of the best walking tours you will ever take, check out Tommy Dew’s Walking History Tour. This is the most comprehensive tour you’ll take in Charleston; it encompasses 10 blocks for about 90-minutes; providing you with the caloric deficit you need in anticipation of future culinary indulgences. Be sure to carry a bottle of water and slather up with sunblock and wear a wide brimmed hat to avoid Southern sunburn.
The tour starts at the Daughters of the Confederacy Museum. If you’re early, check out Marketplace for the best place to find local artisan handiwork for souvenirs. You could spend all day here.
When the British occupied Charleston, they made it a walled city. They enclosed it to protect it from further invasion and try as they might, the Spaniards were unable to break the British stronghold. The marketplace was called Slave market not because slaves were bought and sold there, but because slaves, who then were used as household servants came here to shop for domestic things for their master’s household. It also turns out that a lot of Charleston as it is today is reclaimed from the ocean. This spot on the tour, nearly 2 miles inland, was originally all creek. It was such a wide creek that ocean-liners could ply right through and go further inland as a result of the waterways.
Charleston is now 5 miles across at its widest, but back then was just two miles wide. It is a peninsula much like Manhattan; with the Ashley River on the west and the Cooper River to the east…they both meet at the tip of Charleston, which is called Battery, not unlike Manhattan’s very own Battery Park, at its peninsula tip. The city is set up as a grid, so streets run east to west or north and south and are easy to find and follow.
Charleston was an eight-block rectangular city; it was two blocks wide and four blocks long. It was founded 1680 and is the oldest English city south of Virginia.
Spain had claimed the Deep South in 1565 calling them the St. Augustine Colonies.
The English were about 100 years late, but since they were dominant, they didn’t care, they captured this piece of land and called it their own. This started a turf war with the Spanish for about 35 years.
They were constantly threatened by the Spanish militia, which lead them to build a wall around the city for defense. 14ft high, canons lined it, corner forts, drawbridge complex and a moat down Meeting Street. This allowed the English to come in, gain a foothold, which helped them to go on to dominate the South.
This is why Charleston is called the Mother of the Deep South.
This was the beginning of the English culture south of Virginia. 50 years older than Savannah, 75 years older than Wilmington and 48 years older than New Orleans. It had a big head start. Charleston was the Gateway of the Deep South and grew at a phenomenal rate. It went from non-existent to the 4th largest city in Colonial America right until the late 1700s right up there with NY, Boston and Philadelphia.
It was the largest Southern city until 1820 and was overtaken by New Orleans at that point.
All this was forgotten however because of the war. On December 20, 1860 South Carolina seceded from the Union. The Northern Engineering Troops were working on Fort Sumter at the time of the secession. They took it without a fight. The Southerners dug in; 12,000 South Carolina militiamen got ready for war to blast the Northerners out of the fort and take it back. They didn’t start for nearly four months after secession. The North surrendered it within a day and a half of bombing. The first day of bombing was phenomenal, people hosted parties and politicians gave rousing speeches.
By 1865 Charleston fell from grace and progress passed Charleston by for the next 100 years. Charleston didn’t start to turn the tide until after World War II but nothing really happened until 1974 with the completion of the highway.
Walk for two blocks along Market Street, and you enter the oldest part of town. “The great silver lining of the defeat for the region, but especially Charleston was the lack of pressure for renewal. There was no pressure for development and its old buildings were not torn down in the name of progress.”
The preservation laws were crafted in the 1920s and 30s. and because they were not being challenged by the development sector, they stake the most forward claims for the preservation in the nation and then once there was pressure after World War II in the 50s, 60s, it was too late to do anything because you couldn’t tear down an old building in the name of progress.
“Charleston is the most preserved city and it’s not just the architecture that’s preserved but also the culture because of stagnation and lack of economic draw due to lack of urban renewal. It is ironic since it is because of the Civil war that there are more old structures in accurate state than anywhere else in the country.”
At the intersection of Market and Chamberland Street, you’ll come across an orange building with black iron crosses. This is the Powder Magazine built in 1713 and is the oldest public building in the Carolinas and Georgia. It was part of the defensive scheme of the city, it was just inside the walls of the city and it provided gunpowder for the city’s defenses. The black crosses provide earthquake defense. This building withstood the 7.3 Richter scale earthquake of 1886 which was the largest earthquake to rock the east coast.
Moving toward St. Philips Church and you are about 13ft above sea level. “The British had selected a plateau to build a wall around and had a deep creek to the north and south and a river to the east, on the west side the one side that was inland, (along Meeting Street) was all swamp and marsh. Try as they could the Spanish could not penetrate the British stronghold of Charleston.”
In 1780 the city was attacked by Cornwallis and was bombarded for nearly 6 weeks at which point over 5500 American soldiers surrendered. This was the largest casualty of war for America. Charleston was occupied for 33 months. While they were there, they took whatever they wanted, they broke commodities. Every stick of iron-ore was stolen from the city except for two fences; the ones that surrounded their headquarters and the fence around the Church of England.
Because they were so obnoxious even though the elite of the city were anglophiles, the occupation turns the tide. Everyone went against the English after the occupation. There was more bloodshed in South Carolina than any other colony of America.
This was the bloodiest location of the revolution; South Carolina was called England’s Vietnam.
St. Philips Episcopal Church is the oldest congregation south of Virginia, founded in 1680. It was called the Church of England; since it was an English city the first people to arrive were Anglicans. The name was changed after the American Revolution; since the Americans had just defeated the English and didn’t want to be known as members of the Church of England.
Edward Rutledge signed the Declaration of Independence.
Charles Pinkney is the third framer of the Constitution and is considered one of the fathers of the Constitution.
William Moultrie was a revolutionary general that wreaked havoc for the English and is responsible for sinking the Caribbean fleet.
John C. Calhoun was the father of States Rights; he was a six-time senator, a two-time Vice President. However, States Rights were partially a euphemism to own slaves. He was considered one of the greatest orators in the history of the nation. Abraham Lincoln was his arch enemy and once said of him, that he had “a mind like a file cabinet and voice like a bell” he could recall facts and statistics upon command and had a very melodious voice, as a result southern politicians stuck him on the opposition for 40 years.
He was vilified by the Northerners to such an extent that during the northern occupation, Southern forces exhumed and hid his corpse for 15 years in fear that federal soldiers would “do bad things if they found him.”
As a result of the wall around the city, the houses built were small; the British wanted as many dwellings within the wall as possible to protect the inhabitants. Row houses were common however the problem was that they didn’t ventilate well at all.
The first generation came in and built a huge collection of row houses, and then realized that it was the wrong idea, so the second time around they built freestanding structures separated by small alleys. They also wrapped the structure in windows on all sides so that it allowed for better ventilation.
So anytime you see row houses it is safe to say you are looking at houses inside the wall. They were smaller, much more humble dwellings, the lots outside the wall were much larger and the developers started to build bigger homes, but at that time it was a matter of survival.
It was an English city in survival mode, at the edge of wilderness in conflict with a lot of other powers and it was trying to establish itself.
The wealth came later; the Golden Age was from 1720-1776 when there were no military threats. Be sure to look for an old gray house with red window shutters called Pirates Courtyard built in 1694 making it probably one of the oldest dwellings in the city.
This is right across the street from the French Huguenot Church. The Huguenots were Calvinists from France. They were driven from France by Louis XIV who wanted the country to be Catholic so, in 1685 he revoked the Edict of Nantes. At this same time the Carolinas were just forming, and the first order was Freedom of Religion. So, it was a blessing for them to be able to settle here and establish their church.
Across the street from the Church and a little further south was Dock Street Theatre, one of the first theatres in America. When the British landed there, they were delighted to find cultural development. In 1773 in just one theatrical season, this theatre produced over 180 plays. There was no theatre in the North. The Puritans in Boston labeled entertainment as the portal to your soul where the devil could wreak havoc. Charleston was the first place where one could dance publicly, it hosted the earliest Racetrack, its city lottery is over 200 years ago and it also boasts one of the very first golf courses. Prostitution was legal from the beginning. It was only outlawed after a syphilis epidemic brought back by the soldiers coming home from WWII.
And now this area is considered the Bible belt, a highly conservative area.
At the intersection of Church and Chalmers street a street made completely of cobblestone is Mulatto Alley. This was an area of ill-repute where slave girls came to make more money, to possibly save up to buy their eventual freedom. The slaves worked on the task system. If they finished their assigned tasks, they had the free time to go do other ‘activities’ if they wished.
Continue along Church Street until you get to Broad Street, which is also where you can find the French Quarter Art Walk. You are now in the financial district of Charleston.
During the golden age of skyscrapers, Charleston was a war-torn city, they were in survival mode, and there were no funds for skyscrapers. Skyscrapers just missed them completely. By the time they had the means, the preservation laws made them impossible to build.
This makes Charleston less dense. There are less people living in the same square blocks as say a city like Manhattan. The result of this is civility, ownership of the area, because the residents live, work and play within the same few square blocks there is more civic pride than in a city where say one lives an hour away. Also, as a result of this lack of density, people know each other; this creates accountability and requires civility. It’s no wonder that Charleston is named the ‘the most mannered city in America’.
Look across the west side of Broad, and you’ll notice St. Michael’s Episcopal Church. One of the finest Colonial American churches in the country and the oldest church in Charleston, it was built between 1752 and 1761 and has a 186ft high massively proportioned steeple. It was the focal point of Colonial resistance to the British.
During the Revolutionary period, the church tower was a target for British ship gunners. In order to reduce its visibility, the tower was painted black, which made it even more visible against the blue sky. The steeple continued to function as a navigational landmark and observation post during all major American military conflicts, as well as a fire lookout until the late 19th century.
Move along Church Street and you’ll come upon what’s known as Cabbage Row. This was the inspiration for America’s first Opera, Porgy and Bess by George Gershwin.
Right next door to this is the Heyward-Washington House. Daniel Hayward built this house in 1772. As an English aristocrat, he didn’t want revolution in the colony where he made money. His son Thomas Hayward signed the Declaration of Independence. There was a huge generation gap; father was a Loyalist; the son a Patriot. George Washington stayed in this house for a week in 1779 after which it was called the Heyward-Washington House.
Almost all the houses that you will pass are well over 200 and closer to 300 years old. Some of the larger homes had ‘smaller structures’ attached to them; these were the slave quarters and then the kitchens. It turns out the kitchens were furthest form the house for fear of fire. The temperatures of these kitchens would get into the 130s Fahrenheit in the heat of summer.
Now you’ve come to the courtyard of the first Baptist Church established in 1682 first in Kittery, Maine and moved to Charleston in 1696. Be sure to cut through an alley called Stoll’s Alley, an alley that’s been there forever. You’ll be passing through this alley alongside a HUGE house. This house encompasses the entire length of the alleyway; 14,000 square feet with 16 major rooms.
By now you are outside of the original city wall limits. This alley cuts you through the walled city and brings you out to East Bay Street along the waterfront, where you’ll notice that the homes are a much larger size.
You are likely now at the sea wall built in 1820 with the rock brought in from New England. You can see Fort Sumter at the entrance of the Charleston harbor – Spanish, French, and British have all attacked this channel.
Charleston harbor is one of the most fought after harbors in America. Charleston port is considered the fourth busiest Container port in America and the second most efficient Container Port in the world second only to Rotterdam.
At this point you’re at the end of the tour. If hunger pangs are making it difficult to focus, find your way back to Market street and eat at one of the many restaurants at Charleston City Market. Or then head to Magnolia’s for some mighty fine upscale Low Country cuisine. Check out Culinary Adventures in Charleston for some excellent restaurant recommendations.
Author’s note: I took this tour with Tommy Dew in 2005. This entire article is curated from what I learned during that walking tour with Tommy. Direct quotes are all attributed to him. Accuracies are all courtesy Tommy Dew’s Walking Tour. Inaccuracies are entirely of my doing.
