Ossining borders the eastern shores of the widest part of the Hudson River, the Tappan Zee.

Frederick Philipse bought the area that presently constitutes the Town of Ossining from the Sint Sinck Indians in 1685.

The Sint Sinck are members of the Wappinger Confederacy, who inhabited the land east of Hudson River between what is now Tarrytown and Croton.

[4] His manor extended from Spuyten Duyvil Creek on the border between present-day Manhattan and the Bronx to the Croton River.

In 1838 Benjamin Brandreth built a manufacturing facility for his Vegetable Universal Pills, which became one of the most successful patent medicines in the United States.

Ossining's role in New York's heritage has been recognized by its inclusion, as one of only 14 areas, in an Urban Cultural Park System designed to attract visitors to the state.

[9][10] The Ossining train station provides commuter rail service to Grand Central Terminal in New York City or Croton-Harmon and Poughkeepsie via the Metro-North Railroad's Hudson Line.

NY Waterway also operates a ferry between Ossining and Haverstraw in Rockland County during the rush hours.

The closest example of a federal highway that runs through the village is US 9, along Highland Avenue and Albany Post Road.

The current library collections include 110,000 books, 25,000 non-print items, and 300 newspaper and magazine titles.

[13] Ossining is also the home of the worldwide Maryknoll Catholic missions, as well as the site of the Crotonville Institute, the famous General Electric leadership training facility, founded in 1956.

In seasons 1–3 of AMC's TV series Mad Men, Ossining is home to lead character Don Draper and his family.