Taken from the Riverwalk looking back towards Route 9.

I’d often wondered what these two interesting structures on top of the cliffs are. A conveniently placed information board explains:

Several outstanding historic structures sit high above you on Fort Hill, overlooking Peekskill Bay. The castle-like structure on the left as the Saint Mary’s School for Girls, a beautiful building of brick and stone designed by Ralph Adams Cram. The open quadrangle in the centre of the structure was built in English Tudor-Gothic style, reminiscent of Cram’s masterpieces on the Princeton University campus.

Saint Mary’s was an all girl’s boarding school that catered to grades 8-12. Classes focused on college preparation in the arts and sciences, with a rigorous physical education curriculum. The school closed in 1977, and much of the land was purchased by the City of Peekskill. The site as used as the setting of the fictional TV series “Facts of Life” from 1979 to 1988 and is now the Chateau Rive Apartment complex.

The teachers at the shool, Episcopal Sisters of Saint Mary, arrived in Peekskill in 1872 and departed in the 1980s. Their chapel still stands nearby, with just the steeple visible behind the trees. This is the oldest building on the hill, designed by Church Architect Henry Congdon and built in 1890.

The large convent building, made of stone that was quarried on the hill, is joined to the chapel by a cloister and was built in 1905. The convent was the center of the Community of St. Mary, where the Sisters cared for their sick and infirm, trained their novices, prepared the Altar Bread, designed the Church vestments, and wrote in the Scriptorium.

The nearby Priest’s House (above, and on the right in the first picture) the most visible building on Mount Saint Gabriel (Fort Hill) was constructed in 1903, and is now a private residence.

An article on the New York History Blog (Peekskill’s Historic Community of St Mary) is also worth a read.