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Westport is one of the most attractive areas on Connecticut's Gold Coast. Agriculture was the first major industry. In the 19th century, Westport had become a shipping center with transport of onions to market being at the hub of this trend. Then in the 20th Century came industrialization and increased popularity of New Yorkers attracted to fashionable Westport. Many artists and writers came resulting in farmers selling off land. Westport then changed from a rural farming community to a suburban development. It became popular because of the proximity to New York. The school system had a superior reputation. Also upscale New York fashion influences continued to grow and attract to this beautiful town. Starting around 1910 the town experienced a cultural expansion. During this period artists, musicians, and authors such as F. Scott Fitzgerald moved to Westport to be free from the commuting demands experienced by business people. The roots of Westport’s reputation as an arts center can be traced back to this period during which it was known as a “creative heaven.”
In the 1950s through to the 1970s baby boomers relocating from New York to the suburbs discovered Westport's culture of artists, musicians and authors. Westport is bordered by Fairfield, Weston, Wilton, Norwalk and Long Island Sound.