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Charleston Streets: Prettiest Streets in Charleston

Charleston is home to some of the prettiest spots in the country. We’re one of the oldest cities in the U.S., so it makes sense that we’d also have some of the most beautiful streets, too. 

But what is it exactly about Charleston streets that make them so… beautiful? We’re setting out to count the ways that this city happens to be one of the prettiest in the South. 

Discover some of the prettiest streets in Charleston — and find out what makes the Holy City so special. 


What makes Charleston’s streets so pretty?

What makes Charleston’s streets so pretty? That’s like asking why the birds sing. 

It’s hard to boil down just what it is that makes the Holy City so stunning. But we thought we could give it a shot. On pretty much all of our tours, you’ll find the following features that help make the prettiest streets in Charleston even prettier.


Cobblestone Pavers

a close up of a street in front of a house

Who doesn’t love cobblestone streets? 

Like most Historic cities in the U.S. and Europe, cobblestone streets are preserved to maintain historical integrity. Of course, it wouldn’t be practical to keep cobblestone streets in every area of a city (and many are already filled in with pavement), but these pavers certainly do add some historic (and dare we say romantic?) charm to a city.

On many of the prettiest streets in Charleston, you’ll find cobblestone pavers. If you’re wandering throughout the Downtown Historic District, there’s a good chance you’ll find these pavers throughout this area.  

This one small architectural feature is part of what makes Charleston’s ambiance so special. 


Iron Gates

a clock on the side of a building

One feature that dominates Charleston’s city landscape is iron gates. While most visitors aren’t familiar with these gates on their first trip to the Holy City, they become enchanted by them by the end of their stay. 

Most of these gates were created after the Civil War (during the war, iron from gates and other non-essential items was melted down to use as bullets!). 

One man, Philip Simmons, was the ironworker to craft over 500 of these beautiful architectural elements. Born on Daniel Island in 1912, Simmons had landed an apprenticeship with an ironworker by the time he was 13. 

In the 1930s, a historical preservation ordinance was established, and there was a growing need for ironworkers to repair old gates. By 1947, Simmons had started creating his own gates as well.

You can see Simmons’s work all over Charleston, including some of the city’s most prominent historic structures, such as the First Baptist Church and the Rhett House. 


Colorful Architecture

a close up of a busy city street

Charleston is quite well-known for its impressive architecture. And candy-colored homes are just some of the features that make Charleston streets so beautiful too.

Some of the prettiest streets in Charleston also feature some of the most eye-catching architecture. Rainbow Row, King Street, and Church Street wouldn’t be quite as handsome if they weren’t home to the Dock Street Theatre, the Riviera Theater, or the French Huguenot Church. 


Beautiful Botanicals

Charleston is home to more than 3,000 species of wild plants! No wonder this city is considered a gardener’s paradise!

Charleston streets truly would be a little less beautiful, if not for the live oaks, Spanish moss, azaleas, and gardenias that grow throughout our fair city. 

Want to see Charleston’s prettiest streets at the prettiest time of year? Visit us during spring in Charleston!


Charleston Streets Vs Alleys: What’s the difference?

a plant in a garden

We don’t often think about the difference between streets, roads, alleys, and other avenues of travel (pun intended!). But there’s a pretty big difference between Charleston’s streets and alleyways.

When Charleston was built (starting back in the 1600s), homes were built on the main streets. But a network of alleyways and passages was also built behind some of the city’s most famous homes. 

While in most cities, the back alleyways were where the housekeeping staff traveled, Charleston’s passages are used by everyone — both us “everyday people” and high society alike. 


Prettiest Streets in Charleston

There are so many pretty streets in Charleston, that this list simply does not do it justice. If you want to see some of Charleston’s prettiest streets (and hear some of the stories behind them), sign up for our Charleston History Tour or Alleyways and Passages Tour.

Check out our Charleston self-guided history tour for some ideas of sites to see.


Rainbow Row

Possibly one of the most photographed Charleston streets, Rainbow Row is actually located on East Bay Street.

This strip of architectural delight stretches from no. 79 to no. 107 East Bay Street. These are the pastel homes that you’ve probably seen in TV shows and movies shot in Charleston. We would say these structures are the Lowcountry’s response to the Painted Ladies in San Francisco — but the homes on our Rainbow Row were painted around the same time as the Painted Ladies!


Broad Street

Broad Street is one of the main streets that cuts east to west in Downtown Charleston. 

Located in the South of Broad neighborhood (or rather, the northern boundary of this neighborhood), it’s home to the Cathedral of St. John the Baptist, Washington Park, St. Michael’s Church, and the Old Exchange.

Thanks to its location on the tip of the peninsula, it also gets some pretty good water views, too.  


King Street

King Street is one of Charleston’s busiest thoroughfares

Running north to south, it’s the main shopping district in the city as well as one of the prettiest streets in Charleston. If you walk down King Street (starting at Line Street) to the tip of the peninsula in the Battery, you’ll see a good chunk of Downtown — as well as many famous landmarks along the way. 


Church Street

a sign on the side of a building

Another one of Charleston’s prettiest streets, Church Street, also runs north/south down the peninsula. 

Located in the heart of the Historic District, you’ll see some of the city’s most famous historic landmarks, including the Dock Street Theatre, St. Philip’s Church, and the Heyward-Washington House. Just to the east of the southern end of Church Street is Cobblestone Alleyway, one of the city’s most charming passages. 


Legare Street

Another one of Charleston’s prettiest streets in the South of Broad neighborhood is Legare Street. It’s known for its stately private homes, beautiful gardens, and glorious water views. 

Along Legare, you’ll find the Swordgate House and the Simmon’s Edward House. 

southern mansion

Want to take a break from Charleston and see some of the prettiest streets in our sister city? Check out our Savannah day trip for some ideas.

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