BOOTLEGGERS TRAIL

The story of commerce and trade on Long Island is shaped by a cast of historic and colorful characters who, for centuries, traversed the island from Manhattan to Montauk, and from Fire Island to the Long Island Sound.

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From the 1600s—when thirteen Native American tribes occupied the territory—through the age of privateers during the American Revolution, Long Island was a crossroads of activity, both sanctioned and unsanctioned. As the nation took form along its shores, the island itself became a prized possession, changing hands multiple times amid shifting allegiances and emerging powers.

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During the Revolutionary era, British troops maintained a steady presence on Long Island after the Continental Army withdrew westward in 1776. Intelligence networks operated quietly across the region, including members of General Washington’s famed Culper Spy Ring. Loyalties were uncertain, trust was scarce, and those whose actions were uncovered faced swift and severe consequences from both sides.

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Trade during this period was often driven by privateers—some operating under Congressional authority, others aligned with the Crown—who moved goods captured at sea into regional markets. Sloops and scows became common sights along an inland route extending roughly eight miles from the Sound via the Nissequogue River. These vessels frequently paused at a naturally deep inlet in Smithtown, known as Ships’ Hole, waiting for favorable tides before continuing inland.

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At the same time, coastal traffic arrived from the south, navigating through the barrier islands that line Long Island’s shoreline. As the United States expanded through the 19th century, the Eastern Seaboard grew ever more critical to the movement of goods, materials, and opportunity.

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More than a century later, during the Prohibition era, a nationwide campaign sought to restrict the production and distribution of alcoholic beverages. While formal supply channels were curtailed, public demand endured. In response, a parallel trade emerged, carried out by enterprising operators commonly known as rumrunners and bootleggers.

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Long Island—particularly the rugged, winding terrain of the North Shore—proved uniquely suited to this activity, offering natural concealment and access points. The South Shore and its barrier islands, including Fire Island, also played an essential role. Despite the region’s growing prosperity, discreet commerce continued to flourish beneath the surface of everyday life.

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Across generations, folklore has traced what became known as the “Bootleggers Trail”—a network of routes said to run north from Fire Island through towns such as Islip and Patchogue, past landmarks like the Nissequogue River and Ships’ Hole. Whether by necessity or opportunity, this trail reflects a persistent undercurrent of trade and movement that has long shaped Long Island’s economic and cultural character.