Come along with me on a walk through secret gardens, hidden footpaths, and alleyways laden with ivy, history, and beauty. The walking tour directions below will take you through quiet, tree-lined cobblestone passages off the beaten path and by many of our city’s most iconic and treasured sites. The loveliness of our city never fails to take my breath away. When I did this walk with my husband a couple of weeks ago, I gushed, “Charleston must be the most beautiful city in America.”
Walking Through Charleston’s Hidden Alleys
To start, park by St. Phillips Episcopal Church. The Cumberland Parking Garage is a great option if you struggle with street parking. For some fuel for the walk, stop by Bitty and Beau’s for some of the best coffee in the city served with the sweetest smiles.
Directly past St. Phillips Episcopal Church as you walk toward the Waterfront from Cumberland Street, turn right onto our first alleyway: Philadelphia Alley.
1. Philadelphia Alley
Sitting under the shadow of St. Philip’s Church and running just one block in length between Queen and Cumberland Streets, this storied alley is rich in history and scenery. Formerly known as Cow Alley and as Duelers Alley, this narrow lane was once a path for cattle going to the market. Reportedly, this has been the setting of nearly twenty duels throughout Charleston’s history.
After enjoying the lush scenery and elaborate wrought iron fencing of Philadelphia Alley, turn right onto Queen Street and then left onto Church Street. This walk will give you opportunity to view both the French Huguenot Church (my daughter says it’s pretty in pink) and the historic Dock Street Theatre (with a charming little courtyard and public restrooms). From Church Street, turn right on cobblestoned Chalmers Street, which you will take down to Meeting Street, and then turn left. Once you pass St. Michael’s Church, your next left is St. Michael’s Alley.
2. St. Michael’s Alley
Lined with colonial style homes and stately Italian Cypress trees, this alley is a one-way road that connects Meeting Street to Church Street. Its history includes a duel over the impending Revolutionary War, as well as homes belonging to several individuals important in Charleston’s history, including Clelia Peronneau Matthews McGowan (No. 5 St. Michaels), the first woman to hold public office in the state of South Carolina, and the home of Dubose Heyward (No. 9 St. Michael’s Alley), the author of Porgy and Bess.
Cross over Church Street and you will now be on Elliott Street. Take your first right onto Bedons Alley.
3. Bedons Alley
This charming corridor connects Eliott Street and Tradd Street (arguably one of the loveliest streets on the Charleston peninsula). The buildings on one side of the alley were originally constructed as outbuildings for the large homes on Rainbow Row. Today, you can enjoy meandering by former warehouses and shops that have been beautifully restored as private residences.
From Bedons Alley, turn left onto Tradd Street and then left onto Church Street. Take your first left onto Stolls Alley (or keep venturing down my favorite street on the peninsula to admire the showstopping window boxes and wrought iron work and then loop your way back to Stolls Alley).
4. Stolls Alley
Connecting Church Street to East Bay, right above the Battery, this cobblestone pathway starts wide and narrows to a point where you can extend your arms and touch two walls of history. This is our family’s favorite escape when visiting Rainbow Row or the Battery on hot days. The lush greens provide shade and cool, allowing you to view the beautiful details of the colonial style homes and gardens as you meander down this short jaunt to the Waterfront.
Before moving on to your next hidden alley, take time to admire the homes on Rainbow Row, or watch for dolphins in the harbor. A stop for a climb on the cannons at Waterfront Park may also be in order if you have kiddos with you.
After exiting Stolls Alley on East Bay Street, turn right. Then turn right on Atlantic Street. Your first right off of Atlantic Street is Zig Zag Alley.
5. Zig Zag Alley
As its name suggests, this short, quirky street has a 90-degree turn. I discovered this by car shortly after moving to Charleston and got the fun of trying to extricate myself from this dead-end street in the driveway of a beautiful, historic private residence.
Come back the way you came, departing Zig Zag Alley and continue down Atlantic Street. Turn right onto Meeting Street and walk north and then turn onto Price’s Alley.
6. Price’s Alley
Connecting Meeting Street to King Street, this little cut-through has 300 years of history. Transitioning from marshland to a causeway for a tannery in the mid-1700s, to narrow lots belonging to free people of color, to now boasting intricate gardens and lovely homes . . . at just 350 feet long, this little alley is representative of Charleston’s rich and colorful history.
After reaching King Street, turn right and continue north past Broad Street. If you are hungry for lunch or a snack or just need a coffee, make a stop at Millers All Day, and then continue on to my favorite of the hidden passages on this walk, Unitarian Gateway Walk, which you will find on your left off of King Street.
7. Unitarian Church Gateway Walk
Created and maintained by the Charleston Garden Club, this trail meanders through church yards and ancient graves. You feel like you are in a secret garden, far removed from the hustle and bustle of the downtown peninsula. The footpath will take you by the Unitarian Church, the second oldest congregation in Charleston.
If you turn back around and cross over King Street again, the trail will extend through the Gibbes Museum courtyard and down to Philadelphia Alley. It is called Gateway Walk due to the numerous wrought iron gates you must cross through to enjoy your stroll. It is arguably one of the most beautiful (and coolest!) promenades in Charleston.