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George Washington Spy Trail

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Continental Army officer Benjamin Tallmadge, from a pencil sketch by Col. John Trumbull, assistant to Gen. George Washington. From the Three Village Historical Society collection

By Beverly C. Tyler

Benjamin Tallmadge was the organizer and leader of the Revolutionary War Setauket Culper Spy Ring. Tallmadge, the son of a minister of the Setauket Presbyterian Church, was born in Setauket Feb. 25, 1754.

Tallmadge grew up in Setauket, attended school here with his close friend Abraham Woodhull and, like many residents of Suffolk County, he grew to have a healthy distrust for British authorities in New York. Tallmadge, a college classmate of the Hale brothers, Enoch and Nathan, graduated from Yale in 1773 and, like Nathan Hale, taught school for a time in Connecticut.

A statue of Benjamin Tallmadge at Setauket Elementary School. File photo

Following the skirmishes at Concord and Lexington in Massachusetts, on May 9, 1775, Tallmadge wrote to Hale. “Brother Nathan … America, my friend, at the present period sees such times as She never saw before … everything bids fair for a change … How soon a great, flourishing, and powerful state may arise from that now stigmatized by the Name of Rebels, God only knows. The prospect however for the same seems to be great.”

Tallmadge’s commission as a Continental Army lieutenant was dated June 20, 1776, and he was assigned to Col. John Chester’s Connecticut regiment. He became a regimental adjutant July 22, 1776. His regiment was among those transferred to Brooklyn in time to take part in the Battle of Long Island Aug. 27, 1776. It was the first time Tallmadge took part in any engagement.

Tallmadge wrote a graphic account of the retreat after the battle. “On the evening of the 29th, by 10 o’clock the troops began to retire from the line in such a manner that no chasm was made in the lines … General Washington took his station at the ferry, and superintended the embarkation of the troops. It was one of the most anxious, busy nights that I ever recollect, and being the third in which hardly any of us had closed our eyes in sleep, we were all greatly fatigued … When I stepped into one of the last boats … I left my horse tied to a post at the ferry …The troops having now all safely reached New York, and the fog continuing as thick as ever, I began to think of my favorite horse, and requested leave to return and bring him off. Having obtained permission, I called for a crew of volunteers to go with me, and guiding the boat myself, I obtained my horse and got off some distance into the river before the enemy appeared in Brooklyn. As soon as they reached the ferry we were saluted merrily from their musketry, and finally by their field pieces; but we returned in safety.”

By the time Gen. George Washington was driven north from Manhattan Island in 1776, he was already working on creating a spy network that would provide intelligence on British activities in New York City and on Long Island. Deprived of heavily fortified positions to defend, and with depleted numbers of men and supplies, Washington found it necessary to enable his army to become a moving target, to strike his enemy when and where least expected, and to base his decisions on information gathered from reliable undercover sources. One of the first to operate as a spy on Long lsland was Major John Clark.

“How soon a great, flourishing, and powerful state may arise from that now stigmatized by the Name of Rebels, God only knows.”

— Benjamin Tallmadge

As 1776 came to an end and enlistments expired, Tallmadge was offered a captain’s rank in the 2nd Continental Light Dragoon Regiment commanded by Col. Elisha Sheldon. The new captain accepted his appointment with a feeling of pride, for these commands were subject to Washington’s approval.

By February of 1777, Washington’s first strategic spy network was in place with civilian intelligence expert Nathaniel Sackett conducting covert operations. In addition to his duties as a Dragoon officer, Washington had Tallmadge working with Sackett. Tallmadge, from his position near Fairfield, Connecticut, began receiving intelligence from Major John Clark and Selah Strong on Long Island. The intelligence was most likely brought to him across Long Island Sound by Caleb Brewster, a Continental Army officer, expert seaman and boyhood friend from Setauket.

In a letter to Sackett dated Feb. 25, 1777, Tallmadge wrote that he had “received Intelligence from Long Island by one John Clark that there were no troops at Setauket, but part of two Companies at Huntington and one Company at Oyster Bay . . . That the Militia of Suffolk County was ordered to Meet on the 16th Febry. In order to be drafted for the Ministerial Service but that they were determined not to serve . . . That there are but few who are not friendly to the Cause — that they had beat up four deserters in the western part of the County but that only three had enlisted.”

Clark and Strong stopped spying for Washington on Long Island about September or October 1777 when their work was discovered by Loyalist Lt. Col Richard Hewlett. So, by the time Tallmadge was ready to take over as Washington’s intelligence chief in 1778, he already had a part of the Culper Spy route established with Brewster feeding him information he was gathering from his friends, relatives and other contacts on Long Island. All that needed to be added was a connection from Manhattan to Setauket.

Beverly C. Tyler is Three Village Historical Society historian and author of books available from the society at 93 North Country Road, Setauket. For more information, call 631-751-3730 or visit www.tvhs.org.

One of the 26 signs along the Route 25A corridor from Port Jefferson To Great Neck, which now designate Route 25A as the Washington Spy Trail. Photo by Rita J. Egan

By Rita J. Egan

George Washington and the Long Island Culper Spy Ring continue to make history on the North Shore.

A press conference was held May 18 on the lawn of the Brewster House in East Setauket after the installation of 26 signs along the Route 25A corridor from Port Jefferson To Great Neck, which now designate Route 25A as the Washington Spy Trail. One of the signs, unveiled at the end of the event, is located in front of the Brewster property.

A press conference was held May 18 on the lawn of the Brewster House in East Setauket after the installation of 26 signs along the Route 25A corridor from Port Jefferson To Great Neck, which now designate Route 25A as the Washington Spy Trail. Photo by Rita J. Egan

The installation of signage and the designation comes after almost two decades of work on the part of the North Shore Promotional Alliance. The state road was chosen because President George Washington once traveled it to thank the patriots for helping him win the Revolutionary War, and it was also a route that spy Austin Roe used to pick up and deliver secret messages to military officer and spy Benjamin Tallmadge in Connecticut.

Gloria Rocchio, President of The Ward Melville Heritage Organization and North Shore Promotional Alliance, said that during the days of the Culper Spy Ring in the 1700s the Brewster House was one of only a few homes, and at the time of the American Revolution, the area was occupied by 300 British troops.

“Our community was divided between Loyalist and Patriots who supported the revolution in secret,” she said. “This history is the very history of America. Our efforts over the past 17 years have been to shine a light on our American Revolution and to encourage people to visit those important sites on the North Shore where history was made — the George Washington Spy Trail, Route 25A.

In addition to thanking her fellow members of the NSPA and others for their work, Rochhio acknowledged State Sen. John Flanagan (R-East Northport) and State Assemblyman Steve Englebright (D-Setauket) for introducing a legislative resolution in both the New York State Senate and Assembly that recognizes the dedication of the trail as well as the service of the spy ring members. On the same day, U.S. Rep. Lee Zeldin (R-Shirley) and U.S. Rep. Tom Suozzi (D-Glen Cove) were presenting a similar resolution in congress.

Flanagan thanked those who gave up their free time to dedicate themselves to the project. The senator said he and the other local legislatures who were on hand for the event are proud of their towns.

Brookhaven Town Councilwoman Valerie Cartright and Supervisor Ed Romaine present a proclamation to President of The Ward Melville Heritage Organization, Gloria Rocchio, making May 18 North Shore Promotion Alliance Day in Brookhaven. Photo by Rita J. Egan

“We brag about the places that we come from,” he said. “We like telling people about these types of things.”

Flanagan said he hopes that residents, as well as those who travel to the area will take advantage of the educational experiences the signs call out along the way.

When Englebright stepped up to the podium, he asked State Assemblyman Mike Fitzpatrick (R-St. James) to join him and said he appreciated the partnership with his neighboring assemblyman as well as Flanagan when it came to the legislative resolution that recognizes the area’s historical significance.

“This is a special place,” Englebright said. “Patriots lived here. People put their lives on the line as the first espionage ring for service to our nation.”

Englebright echoed Rocchio’s sentiments of the importance of the signs that pay tribute to the area’s history.

“The memorialization of that through this signage that Gloria referred to, is a chance for us to celebrate that reality, that wonderful beginning of our nation, the role that we played in it,” the assemblyman said. “It’s also important to give a sense of place and sense of context for this and future generations.”

Brookhaven Town Supervisor Ed Romaine (R) and Councilwoman Valerie Cartright (D-Port Jefferson Station) presented a proclamation to Rocchio, which made May 18 North Shore Promotion Alliance Day in Brookhaven. Romaine also reflected on the historical importance of the day.

Local politicians following the enveiling of the Washington Spy Trail sign along 25A. Photo by Rita J. Egan

“Today we remember our history,” he said. “Today we remember ordinary people, living ordinary lives, who were called upon to do extraordinary things.”

John Tsunis, Chairman and CEO of Gold Coast Bank and owner of Holiday Inn Express Stony Brook, introduced Harry Janson, Sr., who was wounded in Vietnam and received the Purple Heart, a medal that originated from Washington’s Badge of Military Merit. Janson, who is on the board of the Long Island State Veterans Home at Stony Brook University, said he believed the members of the Culper Spy Ring — Tallmadge, Roe, Robert Townsend, Abraham Woodhull, Caleb Brewster and Anna Smith Strong — were worthy of the award as well.

“The difference is the example of their bravery,” Janson said. “They performed their bravery in covert, and they took their secrets to their graves.”

Before unveiling the Washington Spy Trail sign in front of the Brewster House, Janson had the same wish as others who worked on the installation of the signage.

“We hope that many of you drive the trail and learn about these brave men and women, and what they did for our country,” Janson said.

Additional Washington Spy Trail signs include ones located on the westbound side of Route 25A at West Broadway in Port Jefferson, by the Long Island Museum in Stony Brook, before the Smithtown Bull in Smithtown and at Lawrence Hill Road in Huntington Station.

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