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Bootleggers Lair - Morning Glory | Bootleggers Trail




Welcome to Bootleggers Lair Estate, a charming oasis that's been around for 200 years, quietly resting on 23 acres along the scenic shoreline bluffs of the Nissequogue River. It's surrounded by hundreds of acres of protected land and private preserve.


The Lair's story is all about how nature and civilization have blended over time, creating a special connection where folks look out for each other and invite others to join in the fun. Come experience its legendary charm for yourself!

Bootleggers Lair - Eagle Eye View | Bootleggers Trail



On Site:  Nissequogue River Basin

2 Miles:  Historic Smithtown Village, Golf

3 Miles:  Long Island Sound, State Park, Railroad

5 Miles:  Wineries, Breweries, Museums

6 Miles:  Historic Stonybrook Village

9 Miles:  Historic Nothport Village

10 Miles:  Macarthur Airport

11 Miles:  Historic Port Jefferson - Ferry

14 Miles:  Historic Huntington Village

15 Miles:  Ocean Beaches, Fire Island, Casino

35 Miles:  Hamptons

44 Miles:  JFK and LGA Airports

49 Miles:  New York City

90 Miles:  100+ Golf Courses, Mountains

Bootleggers Lair - Historic Manor House | Bootleggers Trail


Built in 1828, the Manor House is a step back into time with the convenience of modern living and entertaining comfort. Perched high above the Nissequogue River, the residence's commanding presence reflects the grace and confidence of its storied past along Bootleggers Trail during the expanding settlement of Long Island.

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Bootleggers Lair - Delectable Delights | Bootleggers Trail


Farm & Agriculture

Food & Hospitality

Nature & Wildlife

River, Sound & Ocean

Equestrian & Sporting

Health & Wellness

Music and the Arts

Outdoor Life

Golf Enthusiasts

Short Game Learning Preserve



Present your Membership Medallion at Check-in. Medallions Provide Access to Special Relationships & Local Hospitality. It's a Passport to Good Things.


Available: Local Chef Will Purchase The Ingredients, Cook Your Meal, Serve Your Group and Clean The Kitchen Afterwards!


Available: Local Grocery Shopper Will Buy Your Groceries and Deliver Them. Email Your Grocery List and The Shopper Will Take of All The Rest for You.


Available: Curated Selection of Unique Programs, Services, Activities and Delights Tailored for Members in a Natural Healthy Environment


Available: Foodgasms - Organic Farm Produce, Culinary Delights, Soothing Beverages, Tasty Snacks, Hearty Morsels, Farm-to- Table


Estate Referrals:  Wine & Craft, Golf, Boating, Restaurants, Reciprocal Venues, Fire Island...and More!


From The Mouth of The Nissequoge River to Fire Island Inlet

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  – has played an integral role in the steady hum of commercial activity that churns through Long Island.

Bootsie Magou Straight Bourbon Whiskey

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Nissequogue River, Smithtown NY

We'll be in touch shortly. Thank you!

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