Home > Famous Long Island > George Washington's Spy Trail Stretching along Long Island’s North Shore is Route 25A, which originated in the early 1700s and is a major part of the history of Long Island, NY. President George Washington traveled this same route in a 1790 horse-drawn carriage tour on a mission to thank his Long Island supporters and spy ring for their help in winning the American Revolution.

Honoring this Presidential journey, Route 25A is called the George Washington Spy Trail in certain parts. You can travel the same Presidential route on a journey that includes Raynam Hall Museum, home to one of Washington's Culper Spy ring in Oyster Bay.

Or 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.

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

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.

If you're planning a trip to these or any other Long Island attractions, request a free Travel Guide or take a look at our Interactive Map page to start planning your trip.