Bootleggers’ Trail

Escape to Bootleggers Lair, Fire Island’s North Shore haven during the prohibition era along Bootleggers Trail. Host unforgettable events or indulge in year-round rentals at this captivating destination.
Visit: Bootleggers Lair

The story of commerce and trade on Long Island includes 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.

From the 1600s, when 13 Native American tribes occupied the territory, to the privateers of the American Revolution, when the region was a hotbed of legitimate and illicit activity, Long Island was itself a prized possession, changing hands multiple times as a nation took shape on her shores.

During the Revolution, the presence of British troops on Long Island was customary after the Continental Army escaped to the west in 1776. Spies for both sides, including members of General Washington’s famous Culper Spy Ring, criss-crossed the island. Trust was at an all-time low among colonists and their British overseers, and traitors on both sides were hanged or shot if their deeds were exposed.

Commerce on Long Island during this period was often dominated by privateers – some sanctioned by the Continental Congress, others loyal to the British Crown. These merchants traded goods that had been pirated at sea. During that time, and continuing after the war, sloops and scows popularized an eight-mile route inland from the Sound along the Nissequogue River. These vessels would often stop to wait out low tides at an unusually deep inlet in Smithtown know as Ships’ Hole, before continuing their journeys.

Meanwhile, other ships sailed up the East Coast, arriving on Long Island through the barrier islands to the south. As America grew during the 1800s, the importance of the Eastern Seaboard to trade and commerce was undeniable.

Fast forward more than a century to the era of Prohibition. A nationwide campaign against the consumption of alcoholic beverages led to the passage of the 18th Amendment in 1929, which made the manufacture, sale and transportation of liquor illegal in the United States. However, neither the possession or consumption of liquor was included in the law, so widespread demand remained – and enterprising business operatives stepped in to fill the void, including gangsters and bootleggers, otherwise known as “rumrunners.”

It’s no secret that Long Island was a bootlegger’s paradise, especially the rugged, undulating terrain of the North Shore, which provided numerous spots for cover. But the South Shore and its barrier islands, including Fire Island, were integral to rumrunning activity, too. The region became a hotbed of hooch, and the opulent wealth of many of its residents did nothing to discourage the clandestine activities of the opportunistic, albeit illegal, entrepreneurs.

No matter what the era, the “Bootleggers Trail” – which folklore suggests led north from Fire Island through towns like Islip and Patchogue, and past such landmarks as the Nissequogue River and Ships’ Hole before reaching the Sound – has played an integral role in the steady hum of commercial activity that churns through Long Island.

It is in that spirit that seeks to celebrate the unique history and charm that are hallmarks of Fire Island. We highlight businesses, events, activities, dining and lodging options, entertainment and so much more. And we promote the unique personality and unmatched vitality that makes Fire Island a one-of-a-kind destination for vacationers from across the country and around the globe.