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The winding roads, high bluffs and historic villages of Suffolk County’s North Shore meander through a history filled the whispers of spies during the Revolutionary War; the shadowy dealings of rum-runners during Prohibition; and the exuberant parties of New York’s elite in the mansions and castles of Gilded Age Long Island. It’s also a place where visitors will find trendy villages, historic sites and a myriad assortment of parks and beaches.

Also known as the George Washington Spy Trail, the area is rich with history. Travel along Rte 25A, which originated in the early 1700s and was used by President George Washington in a 1790 horse-drawn carriage tour to thank his Long Island supporters and spy ring for their help in winning the American Revolution. Sites and markers along the way. Get a taste of Long Island history at the Huntington Militia Arsenal. The eastern end of the trail winds through Smithtown, Stony Brook Village and Setauket, and is considered the best historically preserved portion of Route 25A. This is where you can see a number of sites that Washington encountered on his own journey more than two centuries ago. Seewww.longislandheritagetrail.com

In the 1920s rum-running (the illegal transport of alcohol) moved from the South Shore up to the North Shore purportedly due to the lack of Coast Guard patrol here. By many estimates New Yorkers allowed themselves to be little affected by Prohibition, but many pubs and restaurants (still standing) along the North Shore required the secret password to enter.
Also called the ‘Gold Coast,’ the North Shore region was immortalized in F. Scott Fitzgerald’s book, “The Great Gatsby.” Many of the Gold Coast mansions that grace this scenic coastal area, so-called due to the huge concentration of fortunes once held here, are open for the public to explore.

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Easy Charter Bus

Easy Charter Bus

740 Broadway

New York

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Make safe group travel a priority with Easy Charter Bus!...
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Del Vino Vineyards

Del Vino Vineyards

29 Norwood Road

Northport

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Located on the rolling hills of Northport, Long Island's Gold...
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Ralph’s of Greenport, Inc.
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Harbor Pet

Harbor Pet

120 main St

greenport

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Preservation Long Island

Preservation Long Island

161 Main Street

Cold Spring Harbor

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Moms Favorite Child Care and Preschool LLC
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The Adventure Park at Long Island

The Adventure Park at Long Island

75 Colonial Springs Rd

Wheatley Heights

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Symmetry Closets

Symmetry Closets

1361 Lincoln Ave, Unit #16

Holbrook

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Simply Thai

Simply Thai

852 Montauk Hwy

Copiague

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Habitat for Humanity of Suffolk County.

Habitat for Humanity of Suffolk County.

643 Middle Country Road

Middle Island

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Hamptons Delivery Service INC

Hamptons Delivery Service INC

23 Windwood Court

Westhampton

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Modern Snack Bar

Modern Snack Bar

628 Main Street

Aquebogue

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Travel Guide

Explore world-renowned beaches, historical lighthouses, culinary delights, premiere golf courses, Gatsby-era Gold Coast mansions, and award-winning vineyards on Long Island – New York City’s Beachfront Backyard. Download a copy of the Travel Guide for inspiration and more information to plan your perfect getaway.

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