The general consensus is that this town is the most unnaturally sheltered environment one could ever reside in. Which is why its NOT smart to raise kids here despite popular belief. An aging and isolated hamlet in Northern Westchester, truly lacking in diversity and overall quality of life. The whole 'town' shuts down by the early evening. Although even before the town closes, there's a pitifully scarce amount of things to do still, and many of the towns inhabitants have attitudes, are rude, obnoxious, and pay unnecessarily high taxes for an overly competitive school system that's been steadily declining in nationwide ratings since 2003. Most young adults leave instinctively upon completing there high school education because the town has very little to offer to say the least. Living here is also very costly and unaffordable, and has a very dreary and depressing feel to it with its limited woodsy surroundings and hills. Neighboring towns like Pleasantville to the South, or Mount Kisco to the North are within 10 minute proximity and also have a thousand times more of a real world feel compared to the undesirable, sheltered, and conservative, town of Chappaqua.
"Johns parents insisted that Chappaqua would be a marvelous place to live and raise a family, until John was immersed into the sheltered and disappointing excuse for a town."
"I can't believe I pay such high taxes, this middle school is decrepit, looks like a castle, and smells like garbage."
"There's really nothing to do here is there, besides walk around, eat pizza, and be given loose change and pennies on Halloween instead of candy by local retailer Squires."