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I know Chappaqua has this reputation on these boards and I'm sure it has its fair share of these types, but I have honestly found most moms to be down to earth professionals/previous professionals who value family, community and education over flash and materialism. My kids so far are having more of the childhood you describe you had growing up as opposed to what the OP posted about Armonk. Yes there are nice houses and sleep away camps and beach vacations, and the overall cost of living requires a hefty income, but I have been pleasantly surprised at the general lack of pretentiousness and lululemon around the elementary school.