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There are prestigious yacht clubs in nearly every town on the sound. The sound connects to the ocean. While there are obviously places to dock on the Hudson River, the other side draws more people from Fairfield County due to its proximity. Interstate 95 runs parallel to the New Haven Line. I feel like this side of the county attracts more people because of its location, having a major interstate running through it, and Rye Playland. Playland attracts people from the whole region.
Personally, I like Rye because it has sidewalks, a downtown, a boardwalk, and homes on the water. To answer your question, I think it boils down to preference. I grew up in Northern Westchester where you had no sidewalks where I lived. I always spent time in the lower 914 because I loved the idea of sidewalks and neighborhood where you could meet your friends at on the same street. Larchmont has exactly that, not to mention fantastic views and parks on the water.
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