Growing up in rural Maryland, the idea of a city alley conjured up visions of dark places where only bad things occurred. The reality is that my only alley experiences came from TV and movies. These were the places where Crocodile Dundee was attacked and where Batman’s parents were murdered. You would never catch me in an alley!

That would change when I moved to Charleston. I remember stumbling upon Philadelphia Alley for the first time. I wasn’t sure if it was a public way but I took the plunge anyway. Philadelphia Alley, like many of the Holy City’s alleys, is an incredibly unique and beautiful place. These alleys provide a romantic glimpse into what life was like pre-automobile. I have also found these narrow shaded walkways to provide a welcome respite from a hot summer day.

When people visit, one of my favorite things to do is take them on a tour of Charleston’s alleyways. Since you guys are my peeps, I will extend my alley tour invite.

See how many of the photos you can match to the descriptions below. No cheating!

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1. Surfaced in Belgian block, this alley leads from East Bay Street and frames the most perfect view of St. Philip’s Church.


2. Don’t try to ride your bike down this alley — even walking it may lead to a rolled ankle. This meandering cobblestone alley runs one block South of Broad.


3. This little way, technically a “court,” is home to a combination of old and new houses that connects two Cannonborough-Elliotborough streets.


4. The longest and straightest of Charleston’s alleys, it was once known as “Dueler’s Alley.” (I told you these places are dangerous.)


5. You have probably never heard of or seen this skinny secret alley that starts on Broad Street and runs south. But it’s there, I promise!


6. This South of Broad alley is lined with beautiful homes and connects Church and …


7. Two streets are brought together on the lower east side of the peninsula here, framing a unique river view near an historic watering hole.


8. This little path is a must-see, with a picturesque King Street entry into a lush graveyard walk.


9. This is my favorite alley, but it is easy to miss. This alley from East Bay Street measures a whopping 51 inches across. A truly unique experience!


ANSWERS: 1. Lodge Alley. 2. Longitude Lane. 3. Porters Court. 4. Philadelphia Alley. 5. Four Post Alley. 6. St. Michaels Alley. 7. Unity Alley. 8. Gateway Walk. 9. Stoll’s Alley