Brian Granoff
Ossining: historic charm with Metro-North ease — less than an hour from Grand Central.
Enjoy sweeping Hudson River views and explore Westchester County’s only nationally registered historic downtown, cherished for its stunning Italianate architecture. As the oldest New York State–chartered incorporated village in Westchester County, Ossining is rich with history — from the legendary Sing Sing Prison to its beautiful, storied churches. It is also recognized as one of only 14 designated heritage areas in New York State, reflecting its statewide significance in history and culture.
Ossining is Old in History, Young in Spirit — a place shaped by a vibrant, welcoming, and deeply diverse community whose cultures, traditions, and voices bring every block to life. Here, you’ll find neighbors and newcomers, stories from generations past, and new chapters in the making.
As we Celebrate Ossining 250, we invite neighbors, visitors, and explorers of all ages to walk, listen, and connect.
Explore Our Stories, On Every Street.
Jane’s Walk Ossining, NY is organized by Brian Granoff.
To learn more about local Jane’s Walks or get involved, get in touch using the contact information below:
Did you participate in a Jane’s Walk in this city?