When I was a kid I had a Murray 5-speed bike with a banana seat and high handlebars, and I would ride between my neighborhood, Ossining's Indian Village, and Chilmark, across Pleasantville Road on the other side of Ossining Resevoir. Homes in Chilmark were bigger and nicer than my own. While I rode through those streets I dreamed that someday I'd live there. When I was in high school and ran after wrestling practice at night, I'd run through Chilmark because the hills weren't too rough and there were never any cars to avoid. It's funny how a place can be good for you for different reasons at different ages.
Chilmark was built in the early 60's, and is now a very mature community of tree lined streets with beautiful colonials, capes and ranches on spacious lots. It is the sort of place you'd want to trick or treat on Halloween. While it is in the village of Briarcliff Manor and benefits from village services, the close proximity to Ossining puts it in the Ossining School District. On the west Side of the neighborhood is Chilmark Park, an 8.3 acre facility on the grounds of a former country club. The park has a huge jungle gym, fields, tennis and basketball courts, and lots of open space.
Given the bucolic character of the community, the street names have a similar theme: Orchard, Apple, Farm, Magnolia and Meadow, for example. One notable exception is the "main" street through Chilmark, Macy Road, because the it is a homage to the Macy Estate that used to be here. Macy Mansion is still up the hill, although not technically in the neighborhood.
Compared to other baby boom housing, Chilmark is relatively upscale for the era. The homes and yards are spacious, and pride of ownership is evident wherever you look.
As of July, 2007, there is one addition to Chilmark: me. My family moved into a home I used to jog past in high school and ride by on my bike in the 70's. We love it here, and yes, our children do trick or treat here every Halloween.