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- 1837 – The B&O Railroad completes the Potomac Viaduct, an 830-foot-long covered wooden railroad and wagon bridge that connects with the Winchester & Potomac Railroad at The Point.
- 1842 – A curved Y span is added to the Potomac Viaduct to carry the B&O mainline westward along the Potomac River.
- 1861 – Confederate troops blow up the Potomac Viaduct. Subsequent bridges are destroyed and replaced nine times during the Civil War.
- 1870 – The B&O Railroad completes the last iron span of the new Bollman Bridge.
- 1894 – The B&O tunnels through Maryland Heights and completes a new steel Pratt truss and plate girder bridge built by the Pencoyd Bridge & Construction Co. of Pencoyd, PA. The Bollman Bridge is now used exclusively for horse and wagon traffic.
- 1931 – The B&O enlarges the tunnel and completes a new deck plate girder bridge to straighten its mainline through Harpers Ferry.
- 1936 – The Bollman Bridge is swept away by the record Flood of 1936. The 1894 Pratt truss is surfaced and converted for use by both trains and automobiles. This arrangement continues until 1949, when two new U.S. Route 340 highway bridges are completed across the Potomac and Shenandoah rivers.