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Rye just might have the richest history of any Westchester County town.
The city, perched right on the coast of the Long Island Sound and named by a group of English settlers in 1660, started as a secluded farming community, then became a center for oystering and grist mills, and—after the railroad came through in the 19th century—evolved into a picturesque resort town. Today Rye still attracts in-the-know New York City residents for summer day trips, but it’s also home to a decent number of daily commuters.