Ossining is a perfect example of a 19th century Hudson Valley waterfront community.
Main Street leads up the hill from the river and train station to Ossining’s bustling downtown area, which has a mix of street-level shops and restaurants with apartments, offices and artists’ lofts on the upper floors. The surrounding residential neighborhoods provide homes ranging from modest multifamily homes, rentals and townhouses to grand Victorian homes and mansions overlooking the river.
Ossining, which refers to the town and the village it surrounds, dates back to the Dutch colonial era and now is primarily a bedroom community. Shops, restaurants and services are clustered downtown and along Route 9, and there still are some light-industrial employers scattered around town, particularly along the waterfront.
Ossining was ranked the second-best community to live in Westchester by Westchester Magazine, based on criteria such as diversity, housing costs, parks, recreation, property taxes, proximity to the city, safety, schools, proximity to water, nightlife, shopping and downtown amenities.
Ossining is perfect for people who love the outdoors and hiking. The waterfront offers stunning views of the river and surrounding hills, while the Old Croton Aqueduct Trail, a state-operated linear park, provides hiking and biking paths stretching for miles. The Teatown Lake Reservation, a private nature preserve, provides hiking and activities, many of which are intended for children. The county-owned Croton Point Park, just minutes away, has a beach, large fields, overnight camping, numerous festivals and events. Birdwatchers will be stunned by the bald eagles that now visit the Hudson Valley every winter.
In addition to Ossining’s public schools, there are three parochial schools in the area that teach kindergarten through eighth grade. Ossining High School was included on a list of the country’s top 250 best schools in 2000.
Ossining probably is most famous – or infamous – for being the location of the dreaded “Big House up the River” – Sing Sing Prison. (Ossining’s original name, “Sing Sing,” came from the Native American Sinck Sinck tribe from whom the land was purchased in 1685.) More recently, though, Ossining garnered a bit of pop-culture fame by being one of the primary settings for the television show Mad Men, as the home of Don and Betty Draper.