PLAN WHERE YOU

belong

Favorites

heart icon
X
Close

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.

heart icon white heart icon red heart icon filled
Add to Favorites
The Maidstone Hotel

The Maidstone Hotel

207 Main Street

East Hampton

Visit Website

The Maidstone Hotel & Restaurant is open everyday, all year...

Prices Unavailable for this Property

View More Details
heart icon white heart icon red heart icon filled
Add to Favorites
Heron Suites

Heron Suites

61600 Main Road

Southold

Visit Website

Bayside Hotel in Southold, New York Find wine, water, fine dining...

Prices Unavailable for this Property

View More Details
heart icon white heart icon red heart icon filled
Add to Favorites
Village of Southampton

Village of Southampton

23 Main Street

Southampton

Visit Website

Southampton Village is a historic gem, located in the Town...
heart icon white heart icon red heart icon filled
Add to Favorites
Southampton Cultural Center

Southampton Cultural Center

25 Pond Lane

Southampton

Visit Website

Consistent with the vision of the Village of Southampton where...
heart icon white heart icon red heart icon filled
Add to Favorites
New York Charter Bus Company

New York Charter Bus Company

309 E 14th St #2

New York City

Visit Website

New York Charter Bus Company is one of the leading...
heart icon white heart icon red heart icon filled
Add to Favorites
Home2 Suites by Hilton Long Island Brookhaven

Prices Unavailable for this Property

View More Details
heart icon white heart icon red heart icon filled
Add to Favorites
First Glass Wine Tour

First Glass Wine Tour

Visit Website

Welcome to First Glass Wine Tours of Long Island! “Angelo,...
heart icon white heart icon red heart icon filled
Add to Favorites
Coopers Beach

Coopers Beach

268 Meadow Lane

Southampton
Coopers Beach in Southampton is often rated among the Top...
heart icon white heart icon red heart icon filled
Add to Favorites
Newsday Media Group

Newsday Media Group

235 Pinelawn Road

Melville

Visit Website

The nations 5th largest metropolitan daily newspaper with a circulation...
heart icon white heart icon red heart icon filled
Add to Favorites
Harbor Club at Prime

Harbor Club at Prime

95 New York

Huntington

Visit Website

Situated on the legendary Gold Coast of Long Island, the...
heart icon white heart icon red heart icon filled
Add to Favorites
Tesla Science Center at Wardenclyffe

Tesla Science Center at Wardenclyffe

5 Randall Road

Shoreham

Visit Website

Following the inspiration of Nikola Tesla, we will empower all...
heart icon white heart icon red heart icon filled
Add to Favorites
Long Island Sailing Company

Long Island Sailing Company

Degnon Blvd

Bay Shore

Visit Website

The Long Island Sailing Company provides exceptional sailing charters on...

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.

Get The Guide

This website stores cookies on your computer to improve the website experience and improve our personalized services to you. To find out more about these cookies and our privacy processes please see our privacy policy. By clicking Accept you are granting permission for us to store this cookie. If you do not want us to install this cookie please close your browser window now.