Ossining, NY

Ossining Visual Letter


Ossining is a village situated on the eastern bank of the Hudson River approximately 25 miles north of New York City. It is situated on the northern end of the Tappan Zee at the river’s widest point (approximately 3 miles). Ossining has a population of 25,060 residents (2010 census not including the Town of Ossining) and occupies 6.3 square miles (of which nearly half is water). Ossining’s topography consists of several hills and its elevation ranges from nearly sea level along the river to over 160 feet. 

Community History 

Ossining was founded in 1812 as the Village of Sing Sing. It was renowned for its local deposits of granite, which were used in the construction of the infamous Sing Sing Prison. Ossining also became well-known as a riverport, fishing village, site of the Brandreth Pill Factory, and the Croton Aqueduct which bisected the village and provided water from the reservoir to the north to New York City. The village name was changed to Ossining in 1901. Ossining has experienced a resurgence in recent years after a period of urban decay during which shoppers gravitated from downtown to suburban shopping malls and a substantial portion of Main Street was torn down in the 1970s in a controversial move to provide parking. 

The Village of Ossining is a diverse, well-educated community, which is expected to grow with new single and young families. In the 2020 census, approximately 50% reported Black/African American, Asian, Indigenous, Other, and Mixed Ancestry. In recent years Ossining has seen an influx of new residents from Central and South American countries. People of Latinx descent now comprise over 40% of the village’s population. Ossining has become known as a regional center of diversity and redevelopment. 

Most recently Ossining has won one of New York’s coveted downtown revitalization grants and will receive $10 million to develop a downtown strategic investment plan and implement key projects that advance the community’s vision for revitalization. Many of its buildings are now on the National Register of Historic Buildings, including the entire downtown Main St. crescent and the Sparta neighborhood in the south. Its natural beauty and classic charm have served as the shooting locations for film (Analyze This, Black KkKlansman, In and Out) and television (“Mad Men”, “Jessica Jones”). Proposals have been considered and traffic studies conducted for the revamping of Route 9 to improve traffic flow and provide fixed bike lanes. 


Grace Episcopal Church has formed close relationships with many of the institutions in Ossining. Ossining Children’s Center, located on State Street and founded over 100 years ago by congregants of Grace’s St. Paul’s campus, is a non-profit child care center providing invaluable service to the community. Grace’s Trinity campus is home to the Ossining Food Pantry and the Loaves and Fish dinner program. We also work closely with IFCA (Inter-Faith Council for Action) and served as the founding location for the Ossining Emergency Shelter Partnership, which now operates in conjunction with several other churches and houses of worship in the community. 


Ossining is situated on the Hudson Line of the Metro North Railroad. It is a 45-minute commute from Ossining to Grand Central Station in midtown Manhattan. Ossining is bisected by US Route 9, a major artery that runs north-south through western Westchester County. The village is located within 15 minutes of the New York State Thruway and scenic Taconic Parkway. Westchester County Airport is approximately 35 minutes by car and is a designated reliever airport for the tri-state area, having scheduled service to cities across the eastern United States. 


The Ossining School District serves thousands of children within the village. The district follows the Modified Princeton Plan of grouping children at our 5 Elementary schools together by grade as opposed to geographic location. Ossining High School is nationally recognized for its science research program which has produced nearly 90 semi-finalists and finalists in the Intel/Regeneron Science Talent Search. OHS also offers 41 SUNY-recognized college-level courses. Ossining’s athletics are well known, particularly in basketball. Ossining’s Varsity Girls Basketball Team has won 5 AA State Finals and former OHS student Obi Toppin (Class of 2017) is currently a Forward for the New York Knicks. 

Ossining is also home to a Health Sciences satellite campus of Westchester Community College. Pace University and Mercy College are located close by as well. 

Local Economy 

Ossining is often primarily thought of as a suburb of New York City. And while its location is ideal for commuting (as depicted in Mad Men) it is more than just a bedroom community. Ossining’s largest employer is Sing Sing Correctional Facility. There are also over 60 businesses in village limits. General Electric’s Management Development Institute is located north of downtown in the Crotonville neighborhood. 


Ossining is home to the Open-Door Clinic as well as a wide variety of local practitioners. The nearest general hospital is Northwell Phelps Hospital, a 200-bed facility located 10 minutes south in Sleepy Hollow. Westchester Medical Center is an 800-bed Level-I Trauma Center located 25 minutes away in Valhalla. The only regional Children’s hospital, Maria Fareri, is situated nearby. 

Ossining’s emergency needs are met by the Ossining Volunteer Fire Department (OFD) and the Ossining Volunteer Ambulance Corps (OVAC). OFD has been in operation for over 200 years. It has roughly 450 active members (making it possibly the largest volunteer department in the state) in nine companies located in seven firehouses throughout the Village. OVAC responded to over 3,000 calls in 2020 and is located on Clinton Avenue in the Eastern part of the Village. Ossining (both Town & Village) is served by the Ossining Police Department located on Spring Street. In recent years, the department has made strides in community engagement. 

Local Attractions 

Ossining is most widely known as the home of the Sing Sing Correctional Facility. It is one of the largest employers in the area and feasibility studies are currently being done about developing a large-scale museum, similar to Alcatraz in California. A small museum display is currently housed in the Joseph G. Caputo Community Center. There are plenty of hiking and biking trails in the area, most notably the Croton Aqueduct, which allows access to over 26 miles of trail from Yonkers all the way up to the Croton Reservoir. Ossining is also located in close proximity to the Appalachian Trail, North County Trailway, Crawbuckie Preserve, Teatown Lake Preserve, and Rockefeller Preserve. The nearby village of Sleepy Hollow has several tourist attractions such as Sleepy Hollow Cemetery and the Lyndhurst Mansion, and sees over 100,000 visitors annually each October. Ossining has a wide variety of restaurants, including cuisines such as Italian, Thai, Chinese, Japanese, Ecuadorian, and Peruvian. Community Events are held continuously throughout the year in locations such as the Waterfront, Market Square, and Nelson Park.

Ossining in Pictures