Historic Charleston : Make it a long weekend

Last Updated on September 12, 2023 by

The Charleston Historic District is a National Historic Landmark District home to over 1,400 historic structures. It is made up of five distinct neighborhoods: the Boroughs, Harleston Village, the Shopping District, the French Quarter and South of Broad. 

Other than the 9% sales tax, Historic Charleston is great. There is tons to do and see and learn. So much history including the Revolutionary and Civil Wars, Religious institutions, the slave trade and resulting Gulah/Geechee cultures, two forts, three lighthouses, bird watching, kayaking and quaint little shops and restaurants. There are also several horse drawn carriage tours if that’s your ticket. They add wonderful ambiance to the photos, not to mention the general ambiance of the town.

Every small town in America angling for tourist dollars has basically the same formula – recreate the nostalgia of an earlier era, add in some antique, art and tchotchke shops, sprinkle in some eateries and voila – tourism.

Charleston, by contrast, doesn’t need to contrive any of it. It IS the formula. The streets are lined with hundred year old oak and elm (and palm trees – that was a bit of a surprise), the 200 year old historic homes (each and every one with a historic placard), eateries galore that have been around (or at least recycled) since the Civil War and Charleston is what every small town is trying to be.

Add in the fact the city sits on the sea, and you have a city that has captured my imagination in every way. The tree lined streets and flowering vines everywhere make the historic walks invigorating and lovely to experience. The homes have great outdoor spaces and the wide verandas that you expect in the South, not to mention amazing architecture, facades and elevations. While I will always compare all cities to Boston, Charleston may have to be my measuring stick for the South.

Day One

Despite it being a major southern city, the Historic Charleston area is eminently walkable. You could take a carriage ride for about 50 dollars and spend an hour hitting the city highlights, but we feel walking is the only way to get the true feel of a city. Maybe save those tourist dollars for an evening carriage ride after you’ve taken your time exploring on your own.

In less than five miles, it is possible to see many of the city highlights. Here is our recommended route. It will take you past minimally 20 historic sites and through at least some portion of each of the five neighborhoods. Enlarging the map will show the pins for each of the historic sites we identified on the route. Although you can start anywhere, we recommend starting at the historic city market. It is an easily identifiable landmark, parking is close by, and there are plenty of opportunities for treats when you finish the loop.

Here’s a sample of some of the highlights:

Churches

On to some religious history: Charleston, SC is also known as ‘The Holy City’. “Why?”, you ask. Because of the city’s history of religious tolerance and abundant places of worship. Today, the skyline is defined by over 400 church steeples and many different religions are practiced around town. St. Michael’s Church is absolutely gorgeous inside and out and has one of the most unique sarcophagi I have ever seen in the adjacent cemetery. It is for an ordained Reverend, but also has the Star of David engraved on it. Made me go, ‘Hmmm”. Within this cemetery are two of the signers of the U.S. Constitution – Major General Charles Cotesworth Pinkney and Edward Rutledge. Edward Rutledge was also a signer of the Declaration of Independence. Surprisingly, finding the actual markers proved to be some sort of macabre ‘Where’s Waldo?’. You would think the graves would be clearly marked, but then again, it is a cemetery and not an amusement park.

St. Philip’s Church is the second most prominent church in the city due to its age, design, and all the history surrounding it. Yes, it is on the National Register of Historic Places.

Charles Pinkney, the cousin of Charles Cotesworth Pinkney, who, at 29 years of age was a principle writer of the Constitution is buried here.

Founding Father of the U.S., Christopher Gadsen, is also buried here. Additionally, he was a delegate to the Continental Congress, a brigadier general in the Continental Army during the Revolutionary War, a Lieutenant Governor of SC and the designer of the Gadsden flag. The Gadsden flag was the first to be hung over Ft. Sumter after the Confederacy took it in the Civil War. I guess I see now why it’s so closely tied to claims of racism.

We learned this several days later on our Ft. Sumter Tour where we found out about the rear light range housed in St. Philip’s steeple. This light works is associated with the front range tower light originally located on Fort Sumter Island, but now in the water in front of the island. These two range lights work together to help guide ships through Charleston harbor.

There was also the French Huguenot Church – one of the oldest congregations in Charleston and the only remaining independent Huguenot Church in the country (middle picture); the Circular Congregational Church – designed by Charleston’s leading architect, Robert Mills, who also designed the Washington Monument (first pic); and the First (Scots) Presbyterian Church, founded by a dozen Scottish residents who left the Circular Congregational Church in 1731 and is the 5th oldest church in Charleston.

Historic Buildings and Architecture

As the saying goes, “You can’t swing a dead cat without hitting a historic marker”. Although we have only identified 20 sites, placards, national register of historic places and plaques abound. Historic homes run through the gamut of periods pre- and post-Civil War.

And the window boxes… (Because who doesn’t love a well done window box?!)

And all the landscaped yards with quirky accents, vine/moss covered steps, and iron work make everything look so charming.

I forgot to put the Pink House Gallery with the architectural pictures above and thought it deserved notice because it is one of the oldest buildings in SC and the second oldest residence in Charleston. Plus, it’s just adorable!

Photo Opportunities

And, of course, the route takes you past some can’t miss photo ops like Philadelphia Alley and Rainbow Row. Philadelphia Alley has undergone several name changes over the years but 1811 saw the Charleston City Council settle on Philadelphia Alley. Legend has it the alley was popular for duels including one General Moultrie engaged in by sword. Rainbow Row is also steeped in speculation over the true reason for the pastel colors. One theory is to make it easier for drunk sailors to find their way home. Another insists it was the merchants’ way of indicating what types of items they sold there. Either way, both locations are iconic Charleston photos.

King Street

When we eventually found ourselves on King Street, the wheels completely came off. Maybe for him, but most assuredly not for me. King Street is very similar to Rodeo Drive or the High Street in London. Unlike the quaint antique shops and eateries I talked about earlier, King Street is a high end collection of all things ladies like, and some things they don’t know they like until they walk past it. What more can a girl ask for?! While there are certainly a fair number of DKNY/Steve Madden type shops, there are predominantly (at least to my Neanderthal eye) small businesses with reasonably unique offerings. “We” spent the afternoon shopping, window shopping, and thinking about shopping. Woohoo! I would just like to add that he is an horrible enabler constantly asking, “You want to go into that one?” at each store we passed. And there were a lot of stores. What’s a girl to do? While we did stop in quite a few cute little shops, of note, is that King Street is actually part of this historical walk because it is the second most historically and architecturally significant street in the city. We passed by the lovely brick buildings of the college campus, the beautiful old Kress Building where Civil Rights Sit Ins occurred and an art deco theater.

After working up a solid appetite from the effort of repeatedly (twice) reaching into my back pocket for the credit card, we found ourselves at a Greek café called Saffron. My dogs were barking and I needed some energy so we could get back to the shopping part of our day. It was nearly empty except for a truckload of junior high kids dominating the outdoor seating. The host (college kid) asked us if we wanted inside or outside as he was walking directly toward the inside seating. After seeing the kids, he gave me a bit of a shrug and I said “OK. Inside.” “Thought you might,” he replied. I was okay with this though. We just happened to be having higher than average temps and even higher humidity. Welcome back to the east coast. And, yes, we have turned into old people. We were both channeling our inner “Mr. Wilson.
The restaurant was nearly empty setting my expectations low, but I was starving and the dessert counter was huge, so… Decision made. It is all about the dessert after all. I have to say the gyro was absolutely exceptional. While most gyro is shaved off the spit, this was more like lamb slabs, incredibly moist and tender. And too bad for using trigger words, millennials, moist is exactly the word to describe the lamb. The dolmas were the best we have ever had. Hands down. They came out warm and loaded with a rice/meat mixture that was reminiscent of what I expect Moroccan food to taste like. No vinegar anywhere. Just spicy yumminess. Soo good! A great little unexpected culinary surprise off the tourist path. Of note was the parking lot all their own. Not a small feat where most of the parking for downtown includes a parking garage and then hoofing it to your destination. Still, one of my favorite new cities, too.

Once we were done eating, we did not go back to shopping, as was implied above. We instead went back to our regularly scheduled walk and learned more stuff. We passed by the John Rutledge House Inn on North Broad Street. Remember him from the previous post? He was a signer of the US Constitution. He was also the first governor of SC, the President of SC, Chief Justice of SC and Chief Justice of the US. Busy man. I don’t know where these guys found the time. Especially in the age of candlesticks and coal. I guess it doesn’t hurt that the state only had like a hundred old white dudes at the time, so the really cool jobs just got passed around.

John Rutledge House, aka “America’s most historic inn,” is only one of fifteen homes belonging to the original signers of the Constitution to survive. George Washington breakfasted here with Mrs. Rutledge in 1791. I just love the iron work on this building. Right down the street is the Governor’s Inn originally owned by John’s younger brother, Edward Rutledge, a lawyer who was a signer of the Declaration of Independence, served in the First and Second Continental Congresses, was a prisoner of war during the Revolutionary war, and a governor of South Carolina. So much history in these beautiful old buildings. It’s true. I think I’ve learned more US history history in the past year than at any point in the last 50. Bumps, warts and all, this is still an incredible country with literally thousands of stories of perseverance and success despite great adversity.

Day Two

Spend a day visiting Fort Sumter and Fort Moultrie. These forts, and Fort Sumter in particular, have played critical roles in the history of the US and South Carolina, particularly during the Civil War. Fort Sumter can only be reached by ferry, and reservations are recommended. Fort Moultrie allows for a more leisurely exploration of the site.

When you are done, a trip to Sullivan’s Island Lighthouse is only a hop, skip, and jump away. Round out your day with a stroll down Middle Street on Sullivan’s Island and perhaps dinner at Poe’s. A simple menu of salads, burgers, and the odd seafood taco done exceptionally well. If you’re thinking “Why Poe’s?” – the answer is quite simple really – Edgar Allen Poe, then known as Edgar Perry enlisted in the Navy and spent thirteen months stationed at Fort Moultrie from November 1827.

Day Three

Visit a Plantation

Your last day in Charleston leaves you with a few options. A trip to Charleston would be incomplete without a visit to any one of several plantations. Our choice was to visit Boone Hall Plantation and Gardens. We had two reasons for this. First, the plantation has preserved slave cabins on property, providing a more complete picture of life pre-Civil War. The second was due to its proximity to the Charles Pinckney National Historic Site. We thought it would be an interesting contrast to see the difference between a for-profit site and a National Park Service site. Magnolia Plantation and Gardens is also a very popular choice.

Explore the Water

You may also want to get out on the water. Word of caution – the current can be VERY strong in some places. Even at Shem Creek, the tide has a significant impact on how enjoyable your day is going to be. Take a moment to consult a tide chart before starting your day. We went out two or three times and paddled upstream both ways before we figured out that little tidbit.
Shem Creek is a definite fan favorite, but we also really enjoyed Rantowles Creek. If you can arrange the logistics, put in at Limehouse Bridge Landing and leave a car at the take out location at Bulow Landing. Now you’re off to a great half day of downstream paddling.
Finally, if you want to insure flat water paddling, a trip up north to visit Lake Marion might be your ticket. The powerboat traffic is much heavier here though, so be sure to stay closer to the shore. Ideally, you could paddle into the Santee Nature Preserve or out to the Bluff Unit National Wildlife Refuge. Either is a fairly short paddle from Polly’s Landing.

Visit the CSS Hunley and Magnolia Cemetery

If you are a Civil War buff, a trip to the CSS Hunley Museum is an excellent option. It is responsible for the sinking of the USS Housatonic and the first successful submarine operation in history. It is only only 9-5 on Saturday and 9-3 on Sunday, so plan accordingly. A short drive away is the Magnolia Cemetery which has the remains of all three Hunley crews. It is also a Confederate cemetery with large tracts laid out for specific Civil War military units among the thousands of other gravesites.

Visit Angel Oak

Although it is located on John’s Island, Angel Oak is a Charleston treasure. It is quite probably the oldest living thing in the US. A massive Live Oak with branches well over 100 feet is a sight to behold. It is about a 30 minute drive to the site and your time there completely depends on how much time you want to devote to looking at a tree. I would suggest making it a lunch stop and having a picnic. The park is perfectly suited to this purpose.