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Take a Stroll on the Sing Sing Kill Greenway Trail

Sing Sing Kill Greenway Trail

Location – 95 Broadway, Ossining, New York, 10562

Trail – Sing Sing Kill Greenway Trail

Trail Length – about .45 miles (one way) 

Duration – 20 minutes

The Sing Sing Greenway trail spans almost half a mile one way (At the end of my walk, my Strava app recorded I had gone .87 miles round trip). The walkway follows the Sing Sing Kill or Kill Brook. The trail, which is ADA compliant, is within a gorge that showcases its rocky wall. Traveling downstream creates a sense of peace and meditation and is a great way to end your day.

The Tale of the Sing Sing Kill Greenway Trail

The trail was opened in 2016, but its history is much older. Named after the tribe of Native Americans that lived in the area, the Sint Sincks, the kill or creek is a tributary which runs to the Hudson River. 

The Sint Sinck People:


The words sint sink have been attributed to the meaning of place of stones, place of rocks, or as referenced in a Hudson Valley Magazine article, “stone upon stone.”  The Sint Sincks were part of the Algonquin people and lived within the area of Ossining. In the late 1600s, the Sint Sincks sold their land to Frederick Philipse. Philipse incorporated his new holdings into the Philipsburg Manor.

The Sing Sing Kill:

The creek, which bears the name of the tribe that originally inhabited the land, is an abundant ecosystem. A study conducted in 2016, found that about 14 confirmed aquatic species call the kill their home. Among the inhabitants are two types of frogs, two types of turtles, and seven species of fish. There are also eels and clams and reported but unconfirmed trout. 

The kill has evidence of anthropogenic disturbance, such as a brick floor which shows under the two bridges.  The kill was also used as a water source for drinking, ice, and power. 

The Trail

Beginning of the Sing Sing Kill Greenway:

Sing Sing Kill Greenway trailhead sign.

The Sing Sing Kill Greenway trail has two trailheads, but the easiest place to begin is near the parking lot of the Joseph G. Caputo Community Center. After parking in the lot, there is a large green sign which shows the entrance ramp for the trail, this is the part which is also the ADA accessible entrance as the other end only has a staircase. 

Ossining Visitor Center

The ramp zig zags down to the gorge and passes the tops of trees that grow from its bottom. It levels out under the arches of the bridges overhead where you now walk beneath and overhang of leaves and sides of dirt and rock.

View from the ramp to the Sing Sing Greenway
View from the ramp to the Sing Sing Greenway

After the ramp, a sign showcases a brief history and description of the ecosystem of the kill. 

Middle of the Sing Sing Kill Greenway:

Sing Sing Greenway

Traveling further there is a viewpoint where you can see a mini drop from the uplifted riverbed.

Mini drop from the brick raised riverbed
Mini drop from the brick raised riverbed

The sides of the walkway reveal the rocky foundations of the gorge. And at the top of the hill on the left side is an old rock wall, perhaps it is even a marker erected during Philipse’s acquisition of the land?

Exposed rock on Sing Sing Greenway trail
Exposed rock on Sing Sing Greenway trail

Midway down stream, there is a  rocky mound that juts out like a mini mountain standing next to the trail. 

Rock Mound jutting out
Rock Mound jutting out

End of the Sing Sing Kill Greenway:

Dam and grated section
Dam and grated section

You then continue over a grated surface and the dam beneath. There was plenty of vegetation along the sides of the trail, some of which I recognized as Japanese Knotweed, an invasive species in the area.  

Trail ends
Trail ends

The trail culminates from this path with an entrance of a tunnel that teases the furtherance of the stream which will end at the Hudson River. You could continue up the steps to the road where another green trail marker sign stands, or you can return back to the community center.

Sing Sing Kill continues to the Hudson River
The Sing Sing Kill continues to the Hudson River

After walking the path, why not explore the historic town of Ossining and the riverfront views of the Hudson.

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