George Washington Spy Trail

A Historical Getaway

4 Days

The Spy Ring is credited by General George Washington as being a leading factor in turning the tide of the American Revolution. Historic sites on Long Island take you back to the days of 1778 when Long Island was a hotbed of intrigue under British military occupation. A group of local patriots, determined to assist George Washington win the American Revolution, formed the Culper Spy Ring. Take the 4 day trip to uncover the sites of the Washington Spy Trail.

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Day 1

Take a boat excursion to Execution Rocks lighthouse just off Sand’s Point to learn how British colonial authorities are said to have executed ‘Rebels’ by chaining them to the rocks at low tide, allowing the rising water to drown them. As added torture, the bones of those previously executed were…


Take the Long Island Rail Road to the Port Washington Station on the Port Washington Branch.

Located just east of the village of Lloyd Harbor, on the North Shore of Long Island, the 80-acre refuge consists of forest, beach and ponds. Swim, hike or fish at the location which gets its name from a large rock there that the British used for target practice during the Revolutionary War.


Take the Long Island Rail Road to the Cold Spring Harbor Station on the Port Jefferson Branch.

  • 253 Harbor Road
  • (516) 482-2740

Our extraordinary historic home provides guests with eco-friendly Comfortable Elegance & Hospitality in a Conscious Environment. The Harbor Rose is a home where history and modern living peacefully coexist. Enjoy great attention to details including luxury linens and high quality purified alkaline…

Day 2

Long Island was a center for spy activity during the Revolutionary War and many here were credited by General George Washington for the ‘behind the scenes’ help they gave in winning the war. Although Long Island became a captured British stronghold early in the war at the Battle of Long Island, the…

Located in Huntington, the home survived the advance of the British who overtook the town during the American Revolution. See where Sybil Conklin lived with her children while her husband, David, was held prisoner by the British. Uncover the history within the Conklin Home that the family occupied…

Overnight at The Harbor Rose Bed & Breakfast for Night 2.

Day 3

  • 677 West Montauk Hwy
  • (631) 854-0939

Built in 1697, and expanded in 1772 and 1902, the estate served as headquarters for the British Army on Long Island for a brief time during the Revolutionary War. President George Washington stayed there during his tour of Long Island in 1790. The manor house is furnished with original family pieces…


Take the Long Island Rail Road to the Bay Shore Station on the Montauk Branch.

  • 69 Ocean Avenue
  • (631) 968-2316

The Ocean Bay House is a boutique Bed and Breakfast centrally located on the South Shore of Long Island in the historic town of Bay Shore. Situated on Watchogue Creek, this stunning 1800’s colonial was carefully restored in 2017 and features nine guest rooms with ensuite bathrooms, and modern…

Day 4

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…


Take the Long Island Rail Road to the Stony Brook Station on the Port Jefferson Branch.

Built in 1665 and considered the oldest house in the Town of Brookhaven, the Brewster House was home to six generations of Brewsters. During the American Revolution, Joseph Brewster operated the house as a tavern and general store, entertaining British troops inside. American Patriot Caleb Brewster…

  • 150 Main Street
  • (631) 751-0555

Discover a unique country inn overlooking scenic Stony Brook Harbor with the perfect combination of old world charm and contemporary dining.

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