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Holidays in Ossining

Ossining Tree Lighting Ceremony

The Ossining Tree Lighting Ceremony is one of my favorite Ossining Annual Celebrations. There is music, hot cocoa and cider, treats, and caroling with friends and neighbors. Santa arrives in

Ligghts on jenkins court

Lights on Jenkins Court

Lights on Jenkins Court is the Staples family’s home light show. The show has run each year since 2017 during the holiday season. Jeff started designing and programming holiday light

Ossining Menorah Lighting

Ossining Menorah Lighting

The Chanukah Car Menorah Lighting 2021 will take place on Thursday December 2nd at 5PM. Every year, Chabad Lubavitch of Briarcliff-Ossining organizes a Menorah lighting ceremony to help brighten up

LATEST ARTICLES

The Scariest House in Ossining Just Got Scarier

We discovered the “Scariest House in Ossining” in 2019, but 2021 marks the final year that mastermind Craig Pincus will put his unique hand-made Halloween display for the community. For

Artoberfest 2021 at Bethany Arts Center

Artoberfest at Bethany Arts Center is one of the family events we look forward the most every fall. Last year the event was cancelled but this year they came back

Halloween House on Iroquois

Halloween last year was a bit different  and because so many events were cancelled,. we started a new “Halloween tradition”:  take a Halloween Drive around Ossining. Just like last year, we’re determined

Halloween Lights on Jenkins Court

One of our favorite Ossining Holiday activities is to visit the Staples home for their Annual Holiday Light Show (you can read all about it here). Because last year’s Forest O’Fears event

Event Calendar

Event Calendar

Check out our event calendar for upcoming events and activities in and around Ossining, for families, kids or adults.
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Parks and Playgrounds

Parks and Playgrounds

See the full list of parks and playgrounds in Ossining, including maps, photos, features of each and a few surprises.
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Neighborhoods

Neighborhoods

Explore the different neighborhoods Ossining has to offer, including photos of houses in each neighborhood, homes for sale and more.
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OSSINING VIDEOS

Town of Ossining Video Tour
Ossining Main Street Video Tour
Ossining Old Village Video Tour

what residents love about ossining

“We bought a home and moved to Ossining in 2014, attracted by the riverfront, proximity to NYC, access to Metro North, and the beautiful historical architecture.

And while all of those attributes continue to enhance our life here, it is the community of people that made us fall in love with Ossining. It is a VILLAGE in the best sense of the word. We know how lucky we are to call Ossining home.”

– Catherine W.

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“A string of clouds swirl the oranges and reds into the blanched blue sky that hangs over deep green trees and grey cliffs during sunsets on the Hudson river. This is the view my husband and I fell in love with when we moved to Ossining over three years ago. The views around Ossining continue to pull me in and calm me. Whether it be the sunsets, the historic main street buildings of the village, or foliage that appears everywhere as soon as the frosts of winter are gone— I feel lucky to be treated to gorgeous views daily. The vibrant surroundings match the diverse and loving community. My family is fortunate enough to be a part of the Ossining Union Free School District’s Dual Language program. It’s a unique program that blends English speaking and Spanish speaking homes and aims to help kids graduate from high school “…bilingual, biliterate and multicultural.” Some of the other things that stood out to me in the the Ossining schools are the free full-day Prekindergarten and an award-winning science research program. The Recreation and Parks Department offers as many opportunities as the schools—there is always something to do in Ossining. My kids take swim lessons at the recreation pool, my family gardens with friends at the community garden, and we sled the beautiful snow covered hills in the winter time. As the town changes and grows I continue to love that my family lives here. For the reasons stated above and so many more my husband and I decided to buy our first home in the village of Ossining last year. I’m so happy I get to raise my two children in this town that is ‘Old in History —Young in Spirit.’ – Katie S.
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“We chose to settle down and buy a home in Ossining because of the strong sense of community. People that live here genuinely care about one another and the future of our next generation.

We come together to support local business, help our neighbors and embrace the diversity of our village in all its glory! In addition the ease and beauty of the train commute into Manhattan was a necessity for our family.

We have been here for 6 years and I am grateful we found our home and community in Ossining.”

– Christie

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“Ossining is a true gem; a river town that is at once bucolic and bustling. It’s comprised of wonderful people of substance who value each other and the glorious natural setting which we are blessed to call home. – Mary Y.
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“We didn’t know much about Ossining prior to buying our very first home in a nice condo complex north of the town. After living here for 4 years, we are in love with Ossining and now are looking to buy our forever home here in this lovely town. There are so many things we love here, the community is so warm and welcoming to us as a family with young children. The kids program at Ossining Public Library ranks one of the best in Westchester and we have found friends through their programs. The small cafe, delicious restaurants, beautiful park by the Hudson River, and soon to be opening a local toy store and a brewery, are all perfect for our family. One of the most important parts for our family is to live in a diverse town and Ossining is a very diverse city with their famous bilingual program from preschool up through high school. The education system here is exceptional. – Orm W.
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