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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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Positions Dance Studio

Positions Dance Studio

264 Deer Park Avenue

Babylon

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Usdan

Usdan

185 Colonial Springs Road

Wheatley heights

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G2D Group

G2D Group

36 New York Avenue

Huntington

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One10

One10

569 Broadhollow Road

Melville

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Hamptonsfly

Hamptonsfly

128 Gerard Dr

East Hampton

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Hamptonsfly is bringing the gift of flight to the Hamptonites! Experience...
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Rachel’s of Fire Island

Rachel’s of Fire Island

325 Bay Walk

Ocean Beach

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Rachel's is a Restaurant and Bakery on Bay Walk Ocean...
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Sannino Vineyard and B&B

Sannino Vineyard and B&B

15975 County Road 48

Cutchogue

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The North Fork of Long Island's wine country is where...
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Shelter Island Chamber of Commerce

Shelter Island Chamber of Commerce

PO Box 598

Shelter Island

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Shelter Island is for those who seek respite from the...
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Stony Brook Harbor Kayak & Paddleboard Rentals

Stony Brook Harbor Kayak & Paddleboard Rentals

51 shore rd, Stony Brook NY

Stony Brook

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Stony Brook Harbor Kayak & Paddleboard Rentals is Long Island's...
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Fire Island Boat Charters

Fire Island Boat Charters

18 Oakdale Court

Ridge

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We offer custom day charter trips aboard "Andiamo", our 390...
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North Fork Brewing Company

North Fork Brewing Company

24 East 2nd Street, Suite A

Riverhead

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North Fork Brewing Company is dedicated to creating craft beer...
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Hideaway Bayfront Restaurant

Hideaway Bayfront Restaurant

785 EVERGREEN WALK

Ocean Beach

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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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