In the middle of the century, the Hudson River Railroad was built along the shoreline.
With the village now within an hour's ride of New York City, its population grew over 50 percent between 1845 and 1855.
The railroad's effects on the economy were both beneficial and detrimental.
It enhanced the agricultural business through the crossroads, and spurred development of industry at the waterfront such as Benjamin Brandreth's pill factory.
Industries that had been a source of Ossining's early growth, such as boat-building on the riverside and transportation-related businesses like hotels along Albany Post Road, suffered.
In 1850, the First National Bank built its first building at the site occupied by its successor at South Highland and Croton.

Little new construction took place during the 1860s, due to the war and its aftermath.
The Second Empire Olive Opera House at 63-67 Central Avenue, built around 1865, remains the district's oldest non-residential property.
Croton Avenue saw some development at that time, particularly the rowhouses at 4 and the commercial building at 12.
On Main Street the buildings between 157 and 161 also date from this time, but those that remain have been altered enough to no longer be contributing.
The building at 121 Main Street, built around 1865, retains enough integrity to contribute.
After the war, the village built a monument at South Highland and Croton to the 42 men who had been killed in action with the Union Army.
In the middle of the century, the Hudson River Railroad was built along the shoreline. With the village now within an hour's ride of New York City, its population grew over 50 percent between 1845 and 1855. The railroad's effects on the economy were both beneficial and detrimental. It enhanced the agricultural business through the crossroads, and spurred development of industry at the waterfront such as Benjamin Brandreth's pill factory. Industries that had been a source of Ossining's early growth, such as boat-building on the riverside and transportation-related businesses like hotels along Albany Post Road, suffered. In 1850, the First National Bank built its first building at the site occupied by its successor at South Highland and Croton.
Little new construction took place during the 1860s, due to the war and its aftermath. The Second Empire Olive Opera House at 63-67 Central Avenue, built around 1865, remains the district's oldest non-residential property. Croton Avenue saw some development at that time, particularly the rowhouses at 4 and the commercial building at 12. On Main Street the buildings between 157 and 161 also date from this time, but those that remain have been altered enough to no longer be contributing. The building at 121 Main Street, built around 1865, retains enough integrity to contribute. After the war, the village built a monument at South Highland and Croton to the 42 men who had been killed in action with the Union Army.
Downtown Ossining Historic District