The Charleston Inn
A living piece of Hendersonville’s past
If walls could talk, The Charleston Inn would have more than a few secrets to share. Built in the late 19th century and standing strong through more than a century of change, this historic retreat has played host to weary travelers, town legends, and perhaps even an outlaw or two.
From whispered tales of Civil War soldiers to the curious presence of a certain Wild West gunslinger, the Inn’s past is anything but ordinary. Step inside, and you’re not just booking a stay—you’re stepping into a story still waiting to be told.
A Soldier, A Gunslinger, and the Secrets That Linger
L.R. Chewning wasn’t just any innkeeper—he was a former Confederate soldier with a past full of intrigue. Enlisting in the 4th South Carolina Regiment, he found himself crossing paths with infamous figures, including Jesse James of Missouri.
By 1916, Chewning and his wife, Mattie, took over what was then called the Charleston Boarding House, renaming it the Chewning House. But his story doesn’t end there. Legend suggests that Chewning had ties to the Jesse James gang, a claim still whispered within the walls of the Inn today. The most curious piece of evidence? A framed photograph hanging in the parlor, featuring Chewning himself alongside a figure believed to be Frank James.
Although the full truth remains a mystery, one thing is certain—The Charleston Inn has seen its share of fascinating guests.
The Birth of a Landmark
Imagine stepping off a train in Hendersonville in the late 1800s. The scent of fresh sawdust lingers in the air from new buildings rising along Main Street. Horse-drawn carriages rattle over the dirt roads, ferrying visitors eager to escape the summer heat of the lowlands.
Among them, weary travelers find their way to The Charleston Inn, drawn in by its welcoming front porch and glowing oil lanterns. Resting along the historic Buncombe Turnpike, this place isn’t just a stop for the night—it’s a window into the town’s rapid transformation. With the railroad bringing in new faces and fortunes, Hendersonville was no longer just a waypoint—it was becoming a destination.
A Road That Changed Everything
The Buncombe Turnpike, which ran directly in front of the Inn and is now known as U.S. 25, played a pivotal role in shaping the town. Originally built to connect Greenville, South Carolina, to Greenville, Tennessee, it became a lifeline for commerce and migration. The turnpike linked the “low country” of South Carolina to the mountains of Western North Carolina, leading to the rise of summer retreats for wealthy Charlestonians in the nearby Flat Rock community.
During the Civil War, Flat Rock served as a point of refuge for lowland inhabitants. Today, St. John’s Episcopal Church (built in 1849) still cradles the final resting places of Confederate soldiers and officers who once sought solace in this serene mountain retreat.
The House of Many Names
Time has a way of reshaping places, but some buildings never lose their soul. Over the decades, The Charleston Inn has worn many names—the Harrell House, Bonner House, McCurry Hotel, and even the Claddagh Inn—each reflecting a different chapter in its long history.
Originally dubbed the Smith-Green House, its first owner, W.A. Smith, was a successful attorney who later became mayor of Hendersonville.
He capitalized on the newly built railroad, ushering in an era of prosperity for the town. By 1906, the property took on the name “The Charleston Boarding House,” marking its identity as a welcoming retreat for travelers. In 1929, a week’s stay at the Chewning House cost $15.00. Over the years, the inn changed hands many times, yet it remained a beacon of hospitality.
Architecture and Preservation
Despite the passage of time, the architectural integrity of The Charleston Inn has remained remarkably intact. The original wood floors still guide guests through the halls, the front porch exudes the same charm it did more than a century ago, and some of the original light fixtures continue to illuminate the warm interiors.
In recognition of its historical significance, The Charleston Inn was officially listed on the National Register of Historic Places in 1989. This designation not only preserves its legacy but also ensures that future generations can experience its rich past firsthand.
Timeless: An Old Soul with Fresh Energy
Take a walk through Hendersonville today, and you’ll feel it—a town that wears its history proudly but never lets it slow things down. The same streets that once welcomed train travelers now welcome festivalgoers, food lovers, and those looking for a little escape from the rush of everyday life.
Mom-and-pop shops line the sidewalks, blending with cozy coffeehouses and lively restaurants where locals gather. And at the center of it all, The Charleston Inn still stands, its doors open to travelers just as they were a century ago—offering a place to pause, unwind, and soak in the town’s undeniable charm.
Your Turn to Be a Part of It
For over a century, The Charleston Inn has been more than just a place to stay—it’s been a backdrop for stories big and small. Travelers, dreamers, and even a few legends have passed through its doors, leaving behind whispers of their time here. Now, it’s your turn.
Whether you’re visiting for a weekend escape, a step back in time, or simply a quiet place to unwind, this Inn is waiting to add your story to its walls. Walk the same halls as generations before you, sip coffee in the courtyard where history lingers, and let Hendersonville’s charm work its magic.
Book your stay today, and become part of the legacy.