Long Island Heritage Trail

Discover the ‘Secrets of the North Shore.’

The Long Island Heritage Trail along the North Shore holds fascinating tales history and intrigue. Discover the destination’s colonial spy heritage during the American Revolution, and secrets of the Gold Coast, Prohibition and other fascinating legacies that can be found today.

The main route is today’s 25A rimming picturesque Long Island Sound, harbors and inlets from where the patriots operated whaleboats to row intelligence to Connecticut and to General Washington that helped him win the American Revolution.

President Washington traveled to the North Shore on April 21 to 23, 1790, to thank the patriots and his spies. The Trail traverses Great Neck to Port Jefferson back roads and byways extend the regional route to over 100 miles.

Also, explore sites where bootlegging and rumrunning took place and visit former speakeasies! Using itineraries from Great Neck to Port Jefferson, the visitor will be transported to the era of prohibition and the jazz age!

The mission of the Long Island Heritage Trail is to raise awareness, highlight the history, culture, and attractions of Long Island’s North Shore, and encourage visitors and residents to experience history and culture in a new and exciting way.