The first public train arrived here on July 18, 1849, and in December, the Rutland & Burlington Railroad opened the first rail line across Vermont linking the Connecticut River valley at Bellows Falls and Lake Champlain at Burlington. The route passed between Chester's older North and South villages, and Chester Depot village emerged. Fire destroyed the first station in 1871, and the lessee Vermont Central RR built this one that year. By the 1890s, several industrial and commercial enterprises made Chester Depot one of the busiest stations on the Rutland RR. The State purchased the line in 1963, leasing it in part to the Green Mountain RR. Exceptional in Vermont, this brick station retains its high-style Italianate design and continues in railroad use.