Events in Ossining, NY
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Ossining, NY
Aqueduct arches, a working waterfront, and Sing Sing history
Ossining sits on the east bank of the Hudson about 30 miles north of Manhattan, a village best known for Sing Sing Correctional Facility and the engineering marvel of the Old Croton Aqueduct that runs right through downtown. It pairs a genuinely diverse, walkable center with sweeping river views, and it is one of the more affordable places to plant yourself along the lower Hudson.
Landmarks & Highlights
Old Croton Aqueduct & Double Arch
The stone Double Arch downtown is one of the few places you can stand where the 1842 aqueduct crosses a village street. The Aqueduct Trail runs north-south for miles of flat, shaded walking.
Louis Engel Waterfront Park
Riverfront green space with wide Hudson and Tappan Zee views, boat launch, and a popular spot for the weekend farmers market.
Sing Sing Prison Museum
The long-planned museum tells the story of the historic riverside prison and 19th-century Ossining.
Things to Do in Ossining
- Walk the Old Croton Aqueduct Trail and see the Double Arch and Weir Chamber
- Catch sunset over the Hudson from Louis Engel Waterfront Park
- Shop the Down to Earth Farmers Market on the waterfront (seasonal Saturdays)
- Explore the Ossining Historic District and Sparta hamlet
Food & Drink
Downtown Ossining and the Arcadian Shopping Center offer a strong mix of Ecuadorian, Mexican, and Central American kitchens alongside classic pizzerias, delis, and cafes clustered around Main Street and Croton Avenue.
Getting There
Ossining has its own Metro-North Hudson Line station with direct trains to Grand Central in about 45-55 minutes. Metered and permit parking is available near the station and downtown; the waterfront has a free lot.
When to Visit
Spring and fall are prime aqueduct-walking season. Summer brings the waterfront market and river breezes; winter is quiet but the river views are at their clearest.
Frequently Asked Questions
How far is Ossining from New York City?
Ossining is roughly 30 miles north of Midtown Manhattan, about 45-55 minutes by Metro-North Hudson Line train.
What is Ossining best known for?
Sing Sing Correctional Facility, the Old Croton Aqueduct with its downtown Double Arch, and its Hudson River waterfront.
Is there a farmers market in Ossining?
Yes, the Down to Earth Farmers Market runs seasonally on Saturdays at the Ossining waterfront.