There is not too much to say about the city of Ossining, New York – unless you want to talk about its almost namesake, the Sing Sing prison, built in 1825 by convicts brought in from Auburn Prison. Actually, it was an exact namesake – the town used to be called Sing Sing until the early 20th century (1901), when the local city fathers decided that they don’t want ‘that’ kind of publicity, and changed the name of the town ever so slightly.
The prison’s location – up the Hudson River from New York City – is the source of the idiom, “sent up the river.”
Anyhow, the Sing Sing prison is the main thing about the town. The prison occupies prime real estate on the shore of the Hudson river, and it is located just south of the city train station. They say that the Sing Sing prison is accessible by all means of transportation. And much to the surprise of out-of-towners, the trains that run through Ossining pass right through the prison – or more accurately, when you are riding on the Metro North train from New York to Ossining, you will actually pass through a corridor that has prison walls on both sides of the tracks, for the distance of a few hundred meters.
The prison also has its own river dock and a helipad.
On a street corner in Ossining you can sometimes have a strange experience of a car driver asking for directions to Sing Sing… and you’re wondering if he is just going to visit a friend who’s still in jail, or maybe he was out on bail until his sentence was appealed, but now it’s time for him to be in jail himself. Who knows – you probably would not to ask…
As to the town itself and its “free” residents, it sometimes seems as if the prison is the main employer for the majority of them. Not that you’d necessarily know where your neighbor works, unless you ask – but for a special event, such as the funeral of one of the guards who’s left this world for the great prison in the sky, one can enjoy the sight of a solemn parade of his colleagues, in their black uniform, outside of one of the city’s churches.
As to the rest of the city’s free and gainfully employed residents, most seem to commute to regular jobs in New York City – about an hour’s travel by car or train – or to White Plains, which is even closer than the Big Apple.
The lay of the land of Ossining is actually quite impressive: the center of the town is formed by Highland Avenue, which runs along the Hudson over much higher ground, and Broadway (yup, they have one, as many cities from New York to Vancouver do) runs down to the water, where the train station is located. In historical times, Broadway also carried workers to the boat wharf, down at the river.
The view down to the very wide Hudson river can be seen from many locations downtown, and the view is really quite impressive – this city may actually compare to many of the world’s best riverside cities.
While the local architecture does not offer anything particularly remarkable, the grandeur of the natural environment far surpasses what one might expect from a city that is most well known for its prison.
As far as tourist attractions, historical sites, or even interesting (“recreational”) shopping go, Ossining isn’t exactly a major center for any of them. Although, adventurers may enjoy the Teatown Lake Reservation or the Briarcliff-Peekskill Trailway.
Teatown is an 834-acre lake that provide 14 trails that provide nearly 15 miles of walking paths, through diverse terrain and habitats that ranges from easy/novice to moderately difficult trails. The local habitat provides hikers trails that run through abundant fields, mixed hardwood forests, laurel groves, lakes, streams, swamps and farm land. The Teatown Lake area provides access to the rich biological diversity, of the entire Hudson Hills and Highlands region, which is used annually by over 15,000 hikers for nature study and other outdoor recreational activities including jogging, cross country skiing, and snowshoeing.
Also located inside the Teatown Lake Reservation, the two-acre Wildflower Island is surrounded on all sides by Teatown Lake. Accessible only by walking bridge, Wildflower Island was formed when the Bailey Brook was dammed to create Teatown Lake. It is home to over 230 native and endangered species of wildflowers, which are protected by the island’s remote location and the sanctuary managers – who simply remove invasive alien plants and discourage certain local plants from taking root. The flora of Wildflower Island is unusually diverse and interesting for the observer. Experienced guides lead visitors along the paths on the island, describing the unique features of the present wildflowers, most of which are native to the local New York area. Learn more about the Teatown Lake Reservation attractions at: http://www.teatown.org/
If you enjoy hiking and cross-country skiing, you will be able to connect to the Briarcliff Peekskill Trailway and the Croton Aqueduct Trail by way of the trails at the Teatown Lake Reservation.
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the Town of Ossining north to the Westchester County’s Blue Mountain Reservation in Peekskill. The Briarcliff-Peekskill Trail system is just one element of the county’s extensive trail system that also includes the North County Trailway, South County Trailway, the Bronx River Pathway, and the aforementioned Teatown Lake Reservation trails. From the Briarcliff-Peekskill, hikers can take in many beautiful vistas along the length of the trail system. Highlights of the journey will include the water cascading over the beautiful stone spillway at the Croton Gorge Park, and an incredible view of the Hudson River from the 560-foot high Spitzenberg Mountain at the Blue Mountain Reservation. You can learn more about the Briarcliff-Peekskill Trailway at: http://www.westchestergov.com/parks/
Throughout Westchester County’s 18,000 acres of parks and trails, one can also enjoy swimming, bicycling, fishing, skating, and perhaps even a picnic in the great outdoors. Each weekend, county officials make available a wide range of educational, recreational, entertainment and sporting events for people of all ages and interests.
While Ossining may seem a bit ordinary and boring – next to the Big Apple, it is actually a gateway to a day trip or family vacation that you and your kids will remember forever. Welcome to Ossining!
Author’s Note: Also published here.
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Chuck Saddler writes for the American Travel Ideas blog. If you are looking for a family vacation rental in New York or elsewhere, you owe it to yourself to explore the http://www.findvacationrentals.com/ website, where you can literally find thousands of vacation rentals, available in the United States and around the globe.
Read more articles written by Chuck Saddler
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