Then Again: An early Vermont settler, a Green Mountain Boy, was also a spy | #childabductors

British Gen. Frederick Haldimand, shown here, assigned former Green Mountain Boy Justus Sherwood to operate a spy base on North Hero island on Lake Champlain and to recruit Vermonters to provide information about American troop movements. Image from Wikimedia Commons

Justus Sherwood was many things: early settler in Vermont, land speculator, and member of the Green Mountain Boys. 

He was also a British spy. 

In fact, during the American Revolution, Sherwood was one of the British government’s most trusted agents in North America, admired for his bravery, intelligence and loyalty. Sherwood was eventually appointed chief of the northern division of the British Secret Service, acting as spymaster from a fort on North Hero Island. 

That Sherwood would rub elbows with the likes of Ethan and Ira Allen and other members of the Green Mountain Boys, then swear allegiance to the king, might strike some as the height of treachery. But you have to see things from Sherwood’s perspective. The Green Mountain Boys weren’t created as an anti-British group; they were anti-Yorker. In the years before the Revolution, they had purchased land through the auspices of New Hampshire and therefore fiercely rejected efforts by New York’s colonial government to issue grants to the same land. 

When the war started, Vermonters had to choose a side. Many, including Sherwood, remained loyal to the Crown, while others backed the Revolution. And some, including the Allens, fought for the Colonial cause but perhaps reserved the option of returning to the British side until the outcome of the war became clear. 

Sherwood was born in Connecticut in 1747 and lived there until moving in the early 1770s to the town of Sunderland, in what would become Vermont. The area was then widely known as the New Hampshire Grants, though New York officials begged to differ. 

In 1774, Sherwood married Sarah Bothum (or Bottum) and together they settled in New Haven, where he worked as a surveyor. The trade was much needed in a region just being settled and helped him amass large land holdings. 

In 1776, after the Revolution erupted, Justus was arrested as a Loyalist and was ordered sent to the notorious New-Gate Prison in Connecticut. But his stay was short. In fact, some accounts say he escaped even before reaching New-Gate. Together with Sarah and their two children, Sherwood fled north to British-controlled Canada.

When he returned to America the following year, it was as a scout for the army of British Gen. John Burgoyne, which was invading south along Lake Champlain. He fought at the Battle of Bennington, and was one of the few survivors in his unit. Burgoyne’s invasion ended with a devastating defeat at the Battle of Saratoga in New York. The British lost more than 7,300 men in the battle, most of whom were captured, but Sherwood was not among them. His war would continue.

Sherwood was entrusted by British Gen. Frederick Haldimand, governor of Canada, to create and run a critical intelligence post on Lake Champlain. With 25 men under his command, Sherwood constructed a wooden fort at Dutchman’s Point on North Hero. The fort, named the Loyal Block House, was situated at the north end of Lake Champlain, which was the main thoroughfare in the region and therefore the most likely route Colonial forces would take if they were to invade Canada. 

The Americans had invaded Canada in 1775, but that assault ended in failure. Rumors of a second invasion swirled through the region in 1778. One report had Gen. Washington amassing an army of 25,000 men in preparation for an invasion that was intended to smash any British hopes of winning the war.  

Part of Sherwin’s mission was to recruit new agents. We don’t know how many he managed to enlist, but we do know that some of them lived behind enemy lines — that is, in Vermont and upstate New York. Their job was simply to report any troop movements they heard about or saw. Agents also passed along copies of newspapers, which sometimes contained information that hadn’t yet reached British authorities in Canada. 

The agents available to Sherwood differed in talent. The British Secret Service trusted one Vermonter named Elnathan Merwin, who seemingly earned the pen name with which he signed his dispatches, Plain Truth. Sherwood praised another agent, Joseph Wright, whose “stability, secrecy and knowledge of the ruling men of Vermont” made him indispensable. 

Another Vermont agent proved less adept. Sgt. Moses Hurlbut showed up drunk at a dance being held at the Arlington neighbor of Gov. Thomas Chittenden, and began openly trying to recruit Vermonters as British spies. 

Sherwood was assigned with trying to lure Vermont back to the British side. As such, he held important meetings — first with Ethan Allen in Castleton and later with Ira Allen at Ile aux Noix in Quebec — to get the influential Vermonters to deliver the region to the British. 

When Sherwood entered Castleton under a flag of peace, Ethan Allen greeted his old comrade, who stood before him in the captain’s uniform of the Queen’s Loyal Rangers. The two took a walk together, during which Allen confessed that he was tired of the war. If that was the case, Sherwood asked him, why didn’t Allen end hostilities with Britain by reuniting with the mother country? 

Sherwood assured Allen that Vermont would be treated as an independent province within Canada and Allen would receive an officer’s commission. Allen responded hotly, saying he wanted no part of any “damned Arnold plan to sell his country and his honor.” Sherwood said he wasn’t being asked to become the next Benedict Arnold. No, Britain was offering Allen a chance to ensure the independent future of Vermont, whose pleas to enter the Union were being ignored by Congress. Allen asked for time to think it over and for Sherwood to arrange a truce between British and Vermont forces. 

When Haldimand heard of the discussions, he put little faith in Ethan Allen’s word. “I am assured by all, that no dependence can be had in him,” he wrote. “(H)is character is well known, and his Followers … are a collection of the most abandoned wretches that ever lived.” 

British spy Justus Sherwood didn’t trust Ira Allen, shown here, because his “studied style…does not appear to us like the undisguised sentiments of an honest heart.” Image courtesy of Vermont Historical Society

Ira Allen apparently shared his brother’s ambivalence about the idea. Historians have long debated how serious the Allens were during the so-called Haldimand Negotiations. Some believe they were keeping their options open, looking out for the best interests of Vermont and, as major landowners here, for their own economic well-being. 

Others think the Allens were craftier still, brilliantly balancing the interests of Britain and the Colonies to protect Vermont’s own interests. Word of the negotiations eventually leaked, which may have been no mistake. News that Vermont leaders were considering joining British Canada may have buffered the territory against territorial claims by New York. If pushed too hard, Congress feared, Vermont might align with Britain. At the same time, the possibility of a deal also kept the British from attacking Vermont. 

Sherwood seemed to understand that the Allens were buying time from both sides, arguing that they “wish to have two strings in their bow, that they may choose the strongest.” Given their reputations, Sherwood was wary of trusting the Allen brothers. Analyzing a letter by Ira to Haldimand, Sherwood and a colleague wrote that “the studied style of form of Allen’s long letter does not appear to us like the undisguised sentiments of an honest heart.” Which was a polite way of saying they thought Ira was lying.

The British placed the Allens on a list of Vermonters they were considering abducting and turning into agents in exchange for their freedom. But the Allens dragged out the talks until the outcome of the war was clear and the British were no longer planning such raids. In practice, the tactic hadn’t been widely successful anway. We know of only one Vermonter who was recruited as a spy this way. Attempts to capture high-profile targets failed. In the end, so did the Haldimand Negotiations. Sherwood couldn’t bring wayward Vermonters back into the British fold. 

After the war, Sherwood lived out his days in Canada. If he thought of Vermont, it might have been with regret that it hadn’t become part of British Canada. During the negotiations, he had explained his feelings about his mission and Vermonters in a letter to one of Haldimand’s aides: “I freely confess (that) I have nothing so much at heart as reclaiming that people, many of whom were once dear to me.”