When the vast Philipse family landholdings in today's Westchester and Putnam counties were confiscated by the state of New York they were divided among new owners.
Elijah Hunter, an officer during the war, bought the tract just south of Sing Sing Kill.
He also started holding prayer meetings at his and other settlers' houses; the group formally became the First Baptist Church in 1790.

The river shoreline became the hub of early development.
Produce from farms inland was brought there to be shipped to New York City via what is now Main Street, which connected to the Albany Post Road, now US 9.
To open the port to even more farmers, the Croton Turnpike (now NY 133) was built early in the 19th century.

Settlement and development began to concentrate around the crossroads.
The Union Hotel, just north of the Croton Turnpike, became the travelers' stop identified with Ossining.
The local Presbyterian congregation built its first meetinghouse at the present site of Trinity Episcopal Church in 1803.
By 1813 it became Sing Sing, Westchester's first incorporated village.
The First Baptist Church built its first building at its current site in 1815.
In 1820, a relocation of the Post Road a thousand feet (305 m) to the east benefited the new village at the expense of Sparta, the unincorporated hamlet a mile (1.6 km) to the south, since Sparta was no longer on the road while Sing Sing and the Union Hotel still were.
Five years later, the local economy was further bolstered when the state built Sing Sing, one of its first prisons, on the river just to the southwest of the village.
Marble quarried by convicts was used to build not only the prison but several other buildings in the area, including Ossining's oldest church, St. Paul's, now Calvary Episcopal Church, downtown outside the historic district, and elsewhere, such as the steps of the state capitol and New York City Hall.

The churches grew with the village.
In 1834, the Baptist church was renovated, and the Presbyterians built a new Greek Revival church.
Many of the commercial buildings in that style along Main Street west of the crossroads were demolished when the Croton Aqueduct, a masonry tunnel, was built in 1839 to connect Croton Dam with the reservoirs in Central Park.
The buildings in that style at 151–155 Main Street, built afterwards further east, survived and were the oldest buildings in the district when it was established, but are no longer extant.
Only the clapboard Italianate house at 23 South Highland, one of the few residences in the district and now its oldest building, survives from the pre-Civil War period.
When the vast Philipse family landholdings in today's Westchester and Putnam counties were confiscated by the state of New York they were divided among new owners. Elijah Hunter, an officer during the war, bought the tract just south of Sing Sing Kill. He also started holding prayer meetings at his and other settlers' houses; the group formally became the First Baptist Church in 1790.
The river shoreline became the hub of early development. Produce from farms inland was brought there to be shipped to New York City via what is now Main Street, which connected to the Albany Post Road, now US 9. To open the port to even more farmers, the Croton Turnpike (now NY 133) was built early in the 19th century.
Settlement and development began to concentrate around the crossroads. The Union Hotel, just north of the Croton Turnpike, became the travelers' stop identified with Ossining. The local Presbyterian congregation built its first meetinghouse at the present site of Trinity Episcopal Church in 1803. By 1813 it became Sing Sing, Westchester's first incorporated village. The First Baptist Church built its first building at its current site in 1815. In 1820, a relocation of the Post Road a thousand feet (305 m) to the east benefited the new village at the expense of Sparta, the unincorporated hamlet a mile (1.6 km) to the south, since Sparta was no longer on the road while Sing Sing and the Union Hotel still were. Five years later, the local economy was further bolstered when the state built Sing Sing, one of its first prisons, on the river just to the southwest of the village. Marble quarried by convicts was used to build not only the prison but several other buildings in the area, including Ossining's oldest church, St. Paul's, now Calvary Episcopal Church, downtown outside the historic district, and elsewhere, such as the steps of the state capitol and New York City Hall.
The churches grew with the village. In 1834, the Baptist church was renovated, and the Presbyterians built a new Greek Revival church. Many of the commercial buildings in that style along Main Street west of the crossroads were demolished when the Croton Aqueduct, a masonry tunnel, was built in 1839 to connect Croton Dam with the reservoirs in Central Park. The buildings in that style at 151–155 Main Street, built afterwards further east, survived and were the oldest buildings in the district when it was established, but are no longer extant. Only the clapboard Italianate house at 23 South Highland, one of the few residences in the district and now its oldest building, survives from the pre-Civil War period.
Downtown Ossining Historic District