The Washington Spy Trail – Spies, Bootleggers & Blue Bloods

Spies, Bootleggers, and Blue Bloods
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Uncover Secrets of Long Island’s Revolutionary Era Spy Ring
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Visit the Mansions and Gardens Where New York’s Blue Bloods Played
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Explore Tales of Bootleggers and Rum Runners on the North Shore
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Attractions

Museums, Arts & Cultural Sites

Historic Sites

Parks, Gardens & Natural Sites

Lodging

Dining, Shopping & Business

Celebrating 250 Years

Join us in commemorating the 250^th anniversary of the signing of the Declaration of Independence with a series of events across Long Island!

Event Date: Oct 15, 2026

LI 250: Colonial Tavern Tasting at the Three Village Inn

Step back in time for the WMHO’s Colonial Tavern Tasting at the Three Village Inn, where guests will enjoy a unique journey through colonial flavors and traditions with tastings curated by Mirabelle Restaurant.

America 250

The Suffolk County 250th Passport Book

The Ward Melville Heritage Organization and the North Shore Promotion Alliance are participating in the Suffolk County 250th “Passport Book,” now available online and as a free download.

Brewster House (c.1665) & Thompson House (c.1709) Group Tours

Step back in time and explore two of Long Island’s most significant historic homes—the Brewster House and the Thompson House, both dating back to the Revolutionary War era. Discover the fascinating stories of the families who lived in these homes and learn how they experienced one of the most pivotal periods in American history.

Private guided tours are available for groups of 10 or more.

To schedule a tour of the Brewster House or Thompson House, please contact the Ward Melville Heritage Organization at 631-751-2244.

North Shore Spy Trail Communities

Port Jefferson, NY

Port Jefferson, NY

Home to America’s earliest shipbuilders, Port Jefferson Village boasts a deep water harbor, historic homes and a vibrant downtown area. The downtown shorefront area features ...

Smithtown / St. James / Kings Park, NY

These three North Shore communities feature historic houses and other structures and large public parks. Smithtown was named after Richard “Bull” Smith, who according to ...

Stony Brook / Setauket NY

Washington’s spy ring operated there, and British soldiers went to the Stony Brook Grist Mill for supplies. In 1941, Ward Melville created the Colonial-style Stony ...

Centerport NY

Centerport is home to the Vanderbilt Museum. There are several restaurants along Route 25A offering visitors a variety of fine dining. Locations of Interest: Centerport ...

Huntington NY

Locations of Interest: Caumsett State Historic ParkHuntington NYNathan Hale MonumentOheka CastleThe Heckscher Museum of Art

OYSTER BAY Bayville Locust Valley

Oyster Bay / Bayville / Locust Valley NY

Oyster Bay Village is known for its many small shops and the wide variety of cooking styles and preparations of the “pearl of the sea” ...

COLD SPRING HARBOR

Cold Spring Harbor, NY

A charming 19th-century whaling port located along Route 25A/Main Street features over 40 merchants offering high quality merchandise. Open 7 days. This small and quaint ...

GLEN COVE SEA CLIFF

Glen Cove / Sea Cliff Ny

From its beginnings in 1668, Glen Cove’s waterfront and varied topography have made it a popular part of the North Shore’s Gold Coast. Prominent American ...

ROSLYN Old Westbury-Brookville o

Roslyn / Old Westbury / Brookville NY

Downtown Roslyn has shops, eateries, the Roslyn Park duck pond and historic homes dating back to the Revolution, are among local sights. Old Westbury has unique boutiques, ...

Great Neck New York

Great Neck NY

A thriving community, Great Neck is the gateway to Long Island’s North Shore. Settled by the Dutch in the 1600s, Great Neck inspired onetime resident ...