How a colonial nickname for avoiding customs duties became a thriving Long Island village

How a colonial nickname for avoiding customs duties became a thriving Long Island village
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In short: Freeport, New York, evolved from a 1640s settlement into a bustling maritime hub. Once a playground for vaudeville stars and a center for commercial oystering, the village today balances its historic waterfront charm with a diverse suburban identity, all while maintaining its own independent municipal electric utility system.

Originally part of the Meroke Indians' territory, the area was settled by Europeans in the 1640s. By 1659, a herdsman named Edward Raynor had established a cabin, leading to the area being known as Raynortown. The name Freeport was officially adopted in 1853, derived from a colonial-era nickname used by ship captains who were not charged customs duties for landing their cargo in the village's waters.

The late 19th and early 20th centuries transformed Freeport into a premier destination. The arrival of the Southside Railroad in 1868 spurred development, and by the early 1900s, the village became a summer retreat for wealthy politicians and theatrical performers. Stars like W.C. Fields and Buster Keaton frequented the area, and the Long Island Good Hearted Thespian Society even hosted parades featuring borrowed elephants. This era also saw industrial innovation, including the 1910 flight of the first American-made monoplane and the founding of the village's municipal electric utility in 1898, which continues to provide residents with lower rates than neighboring communities.

Today, the village is defined by its Nautical Mile along the Woodcleft Canal, a vibrant strip of seafood restaurants and markets that reflects Freeport's enduring connection to the sea. While the commercial oystering industry declined in the early 20th century due to pollution and salinity changes, the village remains a significant center for fishing activity. The landscape is marked by unique historical remnants, such as the Freeport Spite House—built in a single night to defy grid planners—and the ruins of the 1891 Brooklyn Waterworks, which once processed 54 million gallons of water daily.

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