Starting the Summer in Charleston: Old Buildings, New Sights

Live oaks are everywhere in Charleston.

Summer is my season. I love the heat, the humidity, the long hours of sunlight, the soft evenings. Perhaps being born in July in the Midwest gave me a natural affinity, but I think traveling and summer go together like peanut butter and jelly: all that warmth and sun means you can pack light, walk long distances, and absorb a lot of the place you're seeing.

I chose mid-May for a brief visit to South Carolina and Georgia, and the temperatures, mostly in the mid-80s, were perfect. After an unusually cool D.C. spring, this boosted my spirits into summer mode a little bit early. Driving into Charleston on Saturday afternoon via Ashley River Road, I had my car windows down, and the warm wind was filtered through the live oak trees lining the drive.

My first encounter with the distinctively Southern live oak was in New Orleans a few years ago. These trees speak to my heart—with their gnarled, sprawling branches, they have an air of mystery and protectiveness that lends magic to any park or roadside. Just seeing them makes me feel like I'm home. 

I was only in Charleston for about 40 hours, so I couldn't see everything. But I did experience much of the best of it: colorful shutters on 18th and 19th century buildings, excellent seafood, and plenty of live oaks. Please take my unscientific best-of breakdown with a grain of salt, and visit the city one day yourself to make your own list!

Best historic estate that doesn't gloss over its history

Drayton Hall.

Since I had a few hours to go before I could check into my Airbnb, I stopped along Ashley River Road to visit Drayton Hall. The eighteenth-century mansion and grounds are beautiful, and the tour honestly discusses all who lived and worked on the estate, not just the Drayton family. The house is empty of furniture, allowing guides to showcase its architecture and the changes made over almost 300 years. The African American cemetery on the grounds was the first in the nation. 

Best restaurant housed in a former auto shop

Leon's Oyster Shop.

My Airbnb in West Ashley was perfect in every way, and an excellent home base from which to explore. When I asked for recommendations for the historic downtown, my hosts let me know that the best restaurants are, in fact, outside the most touristy areas.

On their advice, I went to Leon's Oyster Shop, which is "on the peninsula," but north of the most visited part of downtown. Repurposing a midcentury auto shop, the oyster bar and restaurant has a vibe that walks the line between hip and casual. The chargrilled oysters were great, but it was actually the side dish I fell in love with: a spectacular marinated cucumber salad with sesame seeds. You can choose indoor or outdoor dining, but even the indoors feels airy, and the front garage door stays open. Leon's also offers free valet parking.

Before and after dinner, I walked around the neighborhood, taking note of the variety of architectural styles. Everything was a little bit worn, in that attractive way that makes you think "maybe I could actually afford a house here," and often colorfully painted. I saw Victorians, foursquares, Craftsman bungalows, and plenty of original windowpanes.

Best use of vintage metal lamps in an open-air market

City Market.

After sunset, I drove further downtown and parked near the City Market. This historic market has existed since the early years of the 19th century, being replaced after a fire in 1841 and refurbished in 2010. It was fun strolling through the spacious corridors, looking at local vendors' wares, people-watching, and listening to street musicians playing near each entrance. My favorite part was actually taking artsy photos of the vintage lamps and the perfect amalgam of brick, wood, and steel in the ceilings.

I spent a bit more time exploring the market district of downtown, but it seemed to be mostly hotels and tourists. The streets are not well lit, and venturing too far beyond Meeting Street or Market Street quickly takes you into dark, isolated areas, even though the streets are well-traveled in the daylight hours. 

Heading back for the night, I nearly took the fender off my rental car while trying to squeeze out of the tiny public lot. I recommend parking only in large garages or using Uber to get around, as downtown parking is difficult.

Best historic church for modern people

St. Stephens Episcopal.

On Sunday morning, I hit up Kudu Coffee for my caffeine fix, and then explored the Ansonborough neighborhood a bit in the quiet residential vicinity of St. Stephens Episcopal Church.

I passed the small, pretty Theodora Park with its tiled fountain (and while lingering there, learned that mosquitos in Charleston do not wait until evening to attack). Rambling around brought me past many lovely old homes, and up and down narrow streets.

The church itself, built in 1836, was small, light-filled, and welcoming. A visiting minister from Massachusetts who was in town for a "blessing of the bicycles" gave a heartfelt sermon, and part of the reason I selected St. Stephens to visit is its inclusivity—it's a church liberal enough for even a D.C. Episcopalian to feel at home in. 

Charleston is home to many historic houses of worship, earning it the nickname "the Holy City." Most of these are churches and synagogues, though—I had to do a Google search to find whether there were any houses of worship for other faiths (only a few, it turns out).

Best diner to live up to its Fodors Guide blurb

After services, I made my way over to Hominy Grill on Rutledge Avenue. Located in a historic Charleston single house, with beadboard walls and a pressed tin ceiling, it's cozy and classic. There's a small courtyard area where you can order a drink while waiting for a table to open up. This place was recommended in my Fodor's Travel guide to the Carolinas and Georgia, and it did not disappoint. I ordered the shrimp and grits, which came with mushrooms, bacon, scallions, and a tinge of lemon. It was perfect, and the "beermosa" was a good complement, even if I was too full of breakfast to actually finish it.

Houses on Radcliffe Street.

Best Instagram opportunity if you like entropy

Wandering from Hominy Grill toward the King Street shops, via Rutledge and then Radcliffe Streets, I found a cool neighborhood mixing residential with more historic houses of worship, such as the 1854 Brith Sholom Beth Israel Synagogue and the 1893 Central Baptist Church.

This area boasts many of the classic Charleston single houses with piazzas, narrow 19th century buildings with both upper and lower porches. My camera got a good workout with all the attractively disheveled views of clapboard and climbing vines, as well as front doors, mailboxes, and other details that had just the right touch of authentic shabby chic.

Best Instagram opportunity if you like neatness

Rainbow Row.

In the downtown historic district, closer to the Battery, I found photo ops like Rainbow Row, where several residences boast attractive pastel colors. The homeowners really keep up with their external paint jobs, which are pristine and Instagram-ready. The street—which, believe it or not, has its own Yelp review page—was part of a very run-down area in the 1930s and 1940s, and it was restored using the Caribbean-inspired colors for which current homeowners uphold the tradition. 

There are also some impressive mansions lining East Bay Street, as you walk south along the seawall toward the Battery. The park at the tip of the peninsula has old cannons and cannonballs set among the live oaks shading its grassy areas and benches, and locals and tourists alike strolling around.

Walking north up Church Street from the park will bring you down some lovely cobblestone streets past restored 18th and 19th century homes. The elegant air is slightly marred by the many large SUVs parked all along one side of the narrow streets, but one can't have everything. 

Best historic surprise in the suburbs

On my way out of town on Monday morning, I stopped for a terrific pour-over at Classic Coffee Roasters back in West Ashley, then called up Google maps to find a post office. A block from the post office, I passed a cemetery with two plaques, one in English and one in Hebrew letters: "Brith Sholom Beth Israel Congregation, 1886."

Apparently, this is one of two older cemeteries belonging to the synagogue I passed downtown on Rutledge Street. It has beautiful old headstones, stone fences, and those timeless live oaks watching over those resting in its grounds. What I most loved, though, was that each gravestone was inscribed both in Hebrew and English.

I'd never visited an Orthodox cemetery before—and I've always enjoyed seeing anything printed in two or more languages, be it a book of poems or furniture assembly instructions. It vividly illustrates how people from each nation and culture arrive in America with their own languages, customs, and distinctive identities—and hopefully keep them, even as they develop another, indefinably American identity alongside.

Brith Sholom cemetery in West Ashley.

In so few hours in Charleston, even after a lot of walking and wonderful discoveries, it's hard to distill a single impression. It's an old city, and some of the suburbs are as appealing as the downtown. It has dozens of historic sites to visit and Southern restaurants to frequent. I think of Washington, D.C., in its driven impatience and intellect, as a young soul, but I think Charleston is an old soul. I'd like to spend a more leisurely visit getting to know it, and coaxing out more of its secrets. After all, in the South, you can't rush things. Especially in summer.