Explore Charleston’s Hidden Passageways and Alleys

By:Kerry Egan

Date:8/17/2017

In many cities—or maybe most—an alley is probably a place to avoid. But Charleston is not most cities.

In fact, some of the most lovely, picturesque, charming and surprising spots in all of the Holy City are the tucked-away alleys, lanes and walkways. These leafy and brick-clad secret passages are often unnoticed, unless you know just where to look. In fact, some of these hidden lanes are so hard to spot that you might even walk right past it while looking for it.

Seeking them out and wandering down them is worth your time. They offer some of the most charming experiences you’ll find in an overwhelmingly charming city. Some are for pedestrians only and offer a peaceful respite from the car-and wagon-driven hubbub of the main streets. An imaginative walker might even convince herself she has stepped back in time. Some are actually public streets, however tiny and narrow, some gardens and churchyards, but they are all open to the public. Here are just a few of our favorites.


Longitude Lane

One of the prettiest passages in the whole city, Longitude Lane is paved with slates and cobblestones, lined with ferns and cast iron plants, and shaded by tall, arching trees. Located off Church Street, Longitude is bordered by ivy-covered garden walls punctuated by deep-set, arched doors leading to centuries-old Charleston-style houses. If there was a street that could be set in a fairy-tale, it’s Longitude Lane.


Philadelphia Alley

Philadelphia Alley is located between Church and State streets, connecting Cumberland and Queen streets. This long, brick-paved alley, located in the French Quarter, shows up on maps of Charleston as far back as the 18th century. It was once known as Duelers Alley. Legend has it that dozens of duels were fought here, and that at least one dueling victim still haunts the alley. Today, you’ll find deep shade, unfurling ferns and mossy brick walls.


Gateway Walk

Walking the entirety of the Gateway Walk is like a secret best-of-Charleston tour. You’ll see many of the most iconic landmarks of Charleston, but in a way most tourists never experience them. Starting in the churchyard of the Unitarian Church and winding its way through the backyards of famous landmarks, the Gateway Walk lets you feel like you’re seeing the secret (and green and leafy) side of Charleston.


Zig Zag Alley

You might think it's hard to believe, but it’s true: Zig Zag Alley is a real place. In fact, it’s a really little place, one of the shortest streets in all of Charleston, or probably South Carolina for that matter. And the name? Well, you can’t miss the meaning: it’s a zigzag. And it’s awfully pretty, too.


Stoll's Alley

Stoll’s Alley connects Church and East Bay streets. Approach it from Church, and it will probably remind you a bit of Longitude Lane. Approach from East Bay, though, and there’s a good chance you’ll walk right by it, even if you’re looking for it. This public street is so narrow that you can stand in the middle of it and touch the buildings on both sides. You really can’t go wrong, no matter which way you decide to walk down it. Start on the Church Street side, and the languid beauty narrows and darkens until you feel like you’re entering a tunnel. Start on the East Bay side, and if you’re like me, you might even laugh at how unexpected and absurd the little alley appears as you hunt for it amid the grand buildings.

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