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.
Explore by Region
126 Main Street / Southampton, NY 11968 / 631 287 1708
75 N Country Rd / Miller Place, 11764 / 631 476 5742
143 Main Street / East Hampton, NY 11937 / 631 324 1770
380 Montauk Highway / Wainscott, NY 11975 / 631 604 5514