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Toomsboro's origins date back to the 19th century, when the expanding railroad system created new communities across central Georgia. Named after Colonel Robert Toombs, a prominent political figure in Georgia history, Toomsboro became a stop on the Central of Georgia Railway. Its establishment as a rail town made it a natural center for commerce and travel in Wilkinson County. Before this, the area was part of lands inhabited by Creek peoples, who lived in the Oconee River region before their displacement.

The economic backbone of Toomsboro in its early years was agriculture. Cotton plantations and smaller farms dominated the landscape, with the railroad providing an outlet for transporting crops to larger markets. The town became a vital stop for shipping agricultural goods, lumber, and other resources. Mills, shops, and small businesses emerged to serve the needs of local farmers and rail travelers. While small, Toomsboro thrived during the height of the cotton era, benefiting from Georgia's larger agricultural economy.

Infrastructure shaped Toomsboro's development, with the railroad at its heart. The depot served as the hub of the town, where goods and passengers flowed daily. Roads connected the community to nearby Irwinton and McIntyre, while regional highways later expanded access. However, the decline of rail traffic in the mid-20th century, combined with agricultural shifts, led to economic challenges. Many residents moved toward larger towns or cities, leaving Toomsboro as a quieter, more rural community.

Despite its small size, Toomsboro has always valued its sense of community. Local churches, schools, and civic groups served as gathering places, fostering relationships among neighbors. The town developed a reputation for resilience, preserving traditions and heritage while adapting to modern realities. Historic buildings, though fewer in number, stand as reminders of the town's earlier vitality and railroad-centered history.

In recent decades, Toomsboro has drawn interest for its unique charm and history. Known as a quintessential small Southern town, it has attracted attention from preservationists and those interested in rural living. While modest, it offers a close-knit environment, affordable housing, and access to the scenic countryside of central Georgia. Today, Toomsboro remains a symbol of small-town resilience, where history and simplicity converge in a peaceful setting.