Heritage Trail

North Shore
North Shore

The Gold Coast area that stretches along Long Island’s North Shore region from Nassau County into Suffolk County, is interwoven with the history of Long Island and was once home to some of the wealthiest families in America. Just a short ride from New York City, F. Scott Fitzgerald immortalized this region in his book, “The Great Gatsby.” Many of the Long Island “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’s perusal and enjoyment. Over a half-dozen former estates have been converted to public use, many offering art galleries and tours, and others open to allow visitors to stroll the grounds and spectacular gardens to get a feel for what life was like for the privileged few.

The entire Rte. 25A corridor is also known as the Long Island Heritage Trail, and includes not just the Long Island Gold Coast region, but also the Washington Spy Trail.

North Shore

The North Shore region also includes many other historic sites and stories of interest. For example on Long Island, rum-running (the illegal transport of alcohol) moved from the South Shore of Long Island to the North Shore after 1923 because of the lack of Coast Guard patrol.

Names for Prohibition activities such as rum-running, bootlegging and speakeasies came into being. The North Shore Promotion Alliance launched an enhanced website at www.longislandheritagetrail.com focused on “Long Island’s Prohibition Secrets Revealed and Joe Sent Me” promotion. The promotion includes fascinating self-drive itineraries. While in the area, shop in seaport villages; tour the homes of President Theodore Roosevelt or Walt Whitman; visit Revolutionary War sites; or catch a star show at the Vanderbilt Museum and Planetarium. 

North Shore
LONG ISLAND SAMPLE ITINERARY Following is an area tour “snapshot itinerary.” Use it alone as a day tour, or combine it with other attractions or regions for longer stays. Ask Discover Long Island how to make these itineraries a reality for your group. GATSBY’S GOLD COAST Just a short ride from New York City on Long Island’s north shore is a place of uninhibited wealth and opulence immortalized in in the setting of “The Great Gatsby.” Many of the Long Island “Gold Coast” mansions that grace this scenic coastal area are open for the public’s perusal and enjoyment.

HIGH FLYING FUN Long Island is rich in aviation history, from the site of Charles Lindberg’s flight to Paris to the construction of the first lunar module.

  • Falaise Mansion, where Charles Lindberg often summered
  • Cradle of Aviation museum
  • Lunch at an aviation themed restaurant
  • American Airpower Museum

MANSIONS AND MUSEUMS Spend a day exploring Long Island’s rich culture. Explore beautiful estates and museums and the summer Whitehouse of President Theodore Roosevelt.