The Untouched History of Old Bridgeport Road in Bolton, Mississippi

Special to The Bolton News

Tucked away in the quiet town of Bolton, Mississippi, lies a modest dirt path with a story far grander than its appearance suggests. Old Bridgeport Road, a narrow stretch of unpaved road less than half a mile long, is one of the state's most significant—and best-preserved—historic thoroughfares. Though it may not receive the same attention as the famed Natchez Trace Parkway, its legacy is no less remarkable.

Designated a Mississippi Landmark, Old Bridgeport Road stands as a physical reminder of the early development of the state’s transportation system. It dates back to 1822, when the Mississippi legislature authorized its construction as the first official route through what was then frontier land—territory acquired in the Choctaw Session. Its primary purpose was to connect the state capital, Jackson, with Vicksburg on the Mississippi River.

By the 1840s, the road had evolved into a vital artery of communication and commerce. It became a designated Post Road, with stagecoaches running regular service between Jackson and Vicksburg, making two trips daily. These wagons carried passengers, mail, and goods, playing a crucial role in the region’s growth and development.

Old Bridgeport Road also bore witness to a darker chapter of American history. During the Civil War, both Union and Confederate troops traversed its rugged path. In 1865, the road saw a surge of movement as Union soldiers made their way to board the Sultana—a steamboat whose tragic explosion would become one of the worst maritime disasters in U.S. history.

Named after the now-extinct community of Bridgeport, the road’s significance extends beyond its own boundaries. It runs adjacent to a recognized Native American site, a former Union Army encampment, and the historic Holly Grove Plantation. This convergence of historical landmarks underscores the area’s cultural and archaeological value.

Despite its importance, Old Bridgeport Road faced an uncertain future in the early 2000s. Proposals to bulldoze and widen the road in 2005 sparked concern among preservationists and local historians. The threat led to the road being listed among Mississippi’s “top 10 most endangered historic properties.” The outcry prompted state and local authorities to reconsider, and eventually, the Mississippi Heritage Trust secured the road’s designation as a protected landmark.

Today, Old Bridgeport Road remains untouched by modern development. It has never been paved, widened, or rerouted—an increasingly rare condition in a world that constantly favors expansion over preservation. As a result, it offers an authentic glimpse into the state’s early infrastructure and stands as a tribute to the people and events that shaped Mississippi's past.

For those interested in experiencing this piece of history firsthand, Old Bridgeport Road can still be explored in its original form. It may not stretch far, but every inch is rich with the echoes of Mississippi’s journey through time.