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How a Charleston Guide Reckons with the City’s Past—and Celebrates Its Present

Toby Smith, who leads tours at the McLeod Plantation, shares the neighborhood she frequents and the sites of reflection she visits.
The Angel Oak South Carolina
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Since 2015, historian Toby Smith has led tours that focus on educating visitors to Charleston’s McLeod Plantation about the enslaved girls and women who once worked on the historic site. “Theirs are the stories of survival and strength,” she says. These women gave many of us the foundation for who we have become today.” Within her own family, Smith is only three generations removed from slavery; her great-great-grandmother Idella was taken from Ghana at the age of three and brought into the markets in Charleston. “I came out of that family and I am grateful. That’s one reason why being at McLeod is so meaningful to me,” she says. Smith sees Charleston as the essence of her family’s heritage, a city filled with reminders of her past and of how far her family has come. Below, the places around town where she goes to reflect, connect, and relax when she’s not giving tours.

Charleston native Toby Smith, who leads tours of the McLeod Plantation

Courtesy Toby Smith

The first stop of the day

“I would start with a drive to the Angel Oak Tree on Johns Island. It represents a connectivity to nature that is still so strong in the Gullah community, including the connection to the water. It takes me back to Africa where it all began. Then, it’s off to the city market to visit Edna’s Lowcountry. Edna is my aunt on my grandmother’s side. Her shop has been in the market since the 1900s. I buy the Bone Sucking sauce and the Sexy and Sassy Garlic seasoning.”

Finding a moment of reflection

“Lunch will be at Bertha’s Kitchen in North Charleston. The family there has supported the Union Heights community so much. But the tip is to time your visit properly so you don’t have to wait an hour: be in line by 11 a.m. or after 1 p.m. My order is the bread pudding, baked chicken, and macaroni. After, I’ll drive to Sullivan’s Island and read the plaque dedicated to the first slaves who came here and made the first journey. It was put up in the mid-'90s. Sullivan’s Island was the Ellis Island for the enslaved. Sometimes I’ll walk to the water and think about how those first few folks who got off the ship continue to impact my life today.”

The Sullivan’s Island Lighthouse, also known as Charleston Light

Henryk Sadura/Alamy

The neighborhood worth exploring

“So much of Charleston is gentrified but the East Side retains the Black culture. There’s the old Cigar Factory where many Black women stood up demanding fair pay in the 1940s. The labor strike inspired the song “We Shall Overcome,” which an African American picketer named Lucille Simmons adapted. Down the street is a statue of a man named Mr. [Philip] Simmons, the most celebrated of Charleston’s 20th-century ironworkers. He embodied a lot of the East Side, and he left a mark on the city in terms of the talents—and values—that sustained him, and in the more than 500 decorative pieces, including gates, fences, balconies, and window grills that he created. The East Side still tugs at hearts. The walk is interesting because it shows the transition from downtown, classic Charleston to urban city. It is a stark shift.”

The McLeod Plantation on James Island, South Carolina

David Stuckel/Alamy

Where to grab a bite to eat

Hannibal’s Kitchen is a place to sit and reflect on what the Black folk of Charleston have given this town and what their legacy is. I eat the scored flounder and their incredible macaroni, with collard greens and an iced tea-lemonade mix. This is the type of place where they always remember your name. It’s a mandatory stop if you’re in Charleston.”

To read more stories and interviews featuring travel industry workers, visit the 1 in 10 Project.