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I just moved to Ossining this year too! I saw the last two posts, and just had to add my thoughts as another happy recent arrival. As mentioned, Ossining has some really nice neighborhoods. Our house has all the land we could need in an area that is quite rustic and peaceful. Neighbors have been great and I get a community feeling that - while it may very well exist - I didn't pick up elsewhere in Westchester. There is a great combination of natural beauty and friendly/interesting people. I honestly smile at the thought of my daughter growing up here.
So one negative..I do find the "downtown" shopping area a little disappointing. No, it is not run down, just sort of an odd mix of stores that, despite some true highlights, is not terribly conducive to foot traffic overall. It's kind of a shame because Main St has river views and cool historic buildings so you can see there is potential there. Not a problem really, as there is other shopping around, but a missed opportunity for sure. It is nice on weekends when the farmers' market is held downtown.
A couple of details for the OP: there is a really unique breakfast spot, the Wobble Cafe, that somehow balances roles as a go-to place for a quiet morning coffee up by the window and a busy neighborhood meetup spot for parents whose kids use the play area in the back. That's quite a trick to pull, but the place has such good vibes that it all works. This is a weekend tradition for us already. Also, just across Route 9A on Ryder Road, where the town really thins out there is the Maryknoll mission. This is a STUNNING stone building, constructed in I think a Korean style, with a spectacular view of river/mountains behind. I always think it gives that corner of Ossining a slightly mystical feel.
Thanks for the posts! This sounds really great. I'm surprised actually that people find Ossinnig so diverse in comparison to other towns around NYC. More since it was a sort of coinsidence I choose to work with Ossining.
But in al the stories above and other stories and pictures I've seen...it seems like a great place to live indeed. Also great to hear a few places and bars and stores local people like to go.
And still, if anyone has anything to add...please share!
Oh! Is there a lot of work in Ossining itself? Or do most people work in NYC or New Jersey? And what kind of work can one do there?
Like the rest of Westchester, most people work in NYC, other Westchester towns (esp., White Plains), and Connecticut. A much smaller percentage work in NJ and Rockland county.
I see some of these posts are a couple of years old, so I was wondering what people thought about living in Ossining now.
I"m wondering about the schools - elementary and HS, since I have an 8 and 14 year old. Also, what's town life like? We've been looking in Croton which has a nice vibe and the schools are ok., but not much of a town life and not very diverse. Still, we are looking for a small town feel.
Been about 20 years since I lived in Ossining.....not sure if it's improved any, but I do remember at night you did not want to walk Spring St. from Broad Ave. to Madison Ave......and I believe they are looking to turn the prison into a Museum of some sort.....and the football team is no longer the Ossining Indians (long standing), now something like the "O's"
Ossining has been a great choice for our family. We have been very happy with the schools. (2nd grade and pre-k). Our test scores are not as great as many Westchester towns, but we have many students who speak English as a second language so they generally have a tougher time with the testing. But I'm very happy with the teachers, administration, curiculum, etc. The high school has an amazing nationally ranked science program. They also have great arts, sports, etc.
The town definitely has a bigger feel than Croton, but I don't think it feels 'big'. The people here really love the community and are proud of the town. We have a great farmer's market, lots of activities via the rec center, and lots of events down at the water.
If you have any other specific questions, I'll be happy to try to help!
I don't think you're going to get the small town feel in Ossining. And contrary to what some other people said, I do find Ossining's downtown run down. I have only been here a year and can't wait to move.
I love Ossining! I've lived here my whole life and it is a very good place. I would recommend this city to anyone moving to Westchester, NY.
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Ossining 2015
