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Shadow soldiers: Lt. Henry Simmons: Lt. Henry Simmons was one of thousands of British soldiers and Loyalists displaced by the American Revolutionary War. His journal of 1777 and 1778 tells how he and his 45 men overcame the elements and established a new homeland along the north shore of the St. Lawrence River.


The Hudson River valley twists a 300-mile path south from Lake Champlain down to the metropolis of New York City and into the Atlantic Ocean. Henry Hudson lent his name to the river after he sailed into its mouth onboard the Half Moon with a crew of British and Dutch seamen in 1609. That same year, Samuel de Champlain followed the Richelieu River south from the St. Lawrence River to the lake to which he too gave his name.

In the 400 years since, the two river valleys and their adjoining lake (the Champlain Canal linking the Hudson to the lake was opened in 1823) have helped shape the military and cultural history of North America. For the United States, the waterways helped trap and defeat the British during their War of Independence; for Canada, they provided royalists with an escape route from American retribution and a pathway to a new home.


The New England rebels of the late 1770s banished Loyalists from towns and homes their families had either owned or leased for generations. One such town was Claverack, on the east bank of the lower Hudson Valley, where Lt. Henry Simmons lived and prospered. He left in August of 1777 to defend the Crown from rebel insurrection and never returned. Eight years passed before he finally received his land grants and led 400 British veterans and families along the Canadian bank of the St. Lawrence River from Quebec to just west of Kingston.

His handwritten journal for the two years between his departure from Claverack and his arrival in Quebec reveal the fortunes--both good and bad--encountered by Loyalist soldiers on their way to building new lives in Canada.

The Simmons' saga began when his parents arrived from Prussia and settled in Theerbos, near the settlement of Claverack, New York, early in the 18th century. The colony was named Claverack Landing and was surrounded by lands purchased by the Dutch from the Mohican Indians in 1662. To the Dutch who worked the fields and farms of Claverack, the village provided sustenance for themselves and the nearby city of Hudson; to New England mariners, Claverack became an inland seaport for shipping and processing whale oil. The town was located on the reach between Storm King Mountain and Hudson, 150 miles upriver from New York City. The whalers and merchants who had come down from Cape Cod, Martha's Vineyard and Nantucket helped Claverack grow into a substantial port town by the early 1700s.

'Henrick Simon' (as he was christened) was born there in 1740. Anglicizing his name to Henry Simmons, he lived peaceably in the lower Hudson Valley well into his fourth decade.

However, by the mid-1770s American patriots were in open rebellion and family patriarchs were pressured to declare themselves either as Tories loyal to the Crown or as American 'patriots' willing to raise arms against the British. Americans attempted to capture Quebec City and managed to hold it under siege during the winter of 1775. They were forced to retreat the following spring when the British fleet arrived and General Guy Carleton began a counterattack a few months later. By the end of the year he had driven the rebels south and gained control of Lake Champlain at Crown Point, the largest military fort in North America at the time. In the spring of 1777, he was replaced by General John Burgoyne, who marched the British army down along the shores of the lake towards Albany, the northernmost city in the Hudson Valley.

American Tories--known as Loyalists to the British--had suffered greatly during this time. Their homes were confiscated, their properties appropriated, and their lives threatened. Henry Simmons was among them and in August 1777 he began to keep a journal in which he wrote of his hasty departure from Claverack. His harried prose and colonial vernacular reflected the spirit of the times.

"The Sixteeth Day of August, 1777, I left my house at Claverack and Sat out with a Compiny of Seven and twenty Men and officers to go to General Burguins armey Which was at the time at Fort Miller."

According to the transcription and interpretation of Simmons' long hand journal by Dr. H. C. Burleigh, the men had travelled "75 miles in 11 days ... through enemy country, likely at night along untrodden paths, fording streams, and hiding in thickets by day. Their food was what they could carry on their backs."

Simmons described his arrival at the Battenkill River and his enlistment in the British army:

"Arifet at the Butten Kill in the flyeing arme the 27th of augt and Was musterct that Same Day and Joint Lt. Co. Je Saups till further ourder aid there we Lay till the 1st of Septr."

Henry Simmons had signed on with the King's Loyal American Regiment commanded by Lt.-Col. Edward Jessup. Jessup was born in the Hudson Valley and became familiar with the lands around Lake Champlain while serving with the British during the French and Indian Wars under General Jeffrey Amherst in 1759.

Jessup had been awarded half a million acres in the Adirondack Mountains for his military service and he and his brother established a community near Albany which they named Jessup's Landing. By 1776, they had joined the regiment of Sir John Johnson, one of the largest landowners in New York and shortly thereafter created their own regiment, the Loyal Rangers.

At the time of Simmons' enlistment, Jessup's regiment was among those pursuing about 2,500 American soldiers who were in retreat from Fort Ticonderoga. The Americans pulled back across Lake Champlain and headed into Vermont just as the British took the fort. Burgoyne ordered the pursuit but his men were surprised by a rear guard action by the local rebel militia, the Green Mountain Boys, who engaged and defeated his men at Hubbardton.


By then Henry Simmons was a lieutenant in the Loyal Rangers commanded by a Hessian officer, Captain Christian Wehr. Simmons described his ordering of two men back to Claverack to get more men and arms, and the false alarm they experienced soon afterwards:

"Chrichtyan havver ... Went home to gitt more men ... the 8th Sept we get arms for 12 men and thath nigh we was Alarrmet as if the enemy were coming But it Wa a fals Larm."

The British army, including Jessup's regiment, continued their pursuit of the Americans who had arrived at Fort Miller. The tattered Continental Army had been regrouped and reorganized by General Phillip Schuyler, and under the command of Horatio Gates had left for Saratoga, New York before the British arrived. According to Simmons' journal, his detachment arrived at Schuyler's estate on "the 10th we gat armes for 9 men more [and by the 13th of September] we ... as fare as Shullers upper Sawmill."

The British army had started their march from Canada with 3,000 British regulars, 4,000 German Hessians, 650 Canadians and Indians, and along the way added Loyalists of the likes of Simmons and Jessup from Vermont and New York. After their defeat at Hubbardton, the British suffered a more significant loss at Bennington, Vermont, when a large force of Hessians--who had been ordered by Burgoyne to attack the town and raid its storage depot--were repulsed and took heavy casualties.

By the time the British army arrived at Saratoga, their ranks had been significantly reduced. The arduous land push from the east bank of the Hudson had left the men fatigued and depleted of supplies. On the other hand, General George Washington ordered reinforcements for the Americans. His most aggressive general, Benedict Arnold, arrived from the south, General Israel Putman came from the north along with reinforcements from Massachusetts, riflemen from Virginia, and militia from all over New England.

The first battle of Saratoga was on Freeman's Farm on September 19, and Henry Simmons described its outcome in his journal:

"... and their We lay until the 19th' till some time in the night and ... that Day our Flying Arme and the Rebels had a Battle at free mans farme But our men Boit the Rebels to Reterin and Kilt betwin 3 and 4 hundaert of the Enmy and we had about two hundred Deat and Wountet."

Three days later and less than two weeks before the second and final battle of Saratoga, Simmons' two men returned from Claverack with reinforcements for Simmons' detachment and a prisoner they had taken on route: "... Haver and Hess Came in agin and Brought 18 men with them and A Commetee man PreSsoner."

Simmons' detachment now consisted of 45 men, all of whom were engaged in the Second Battle of Saratoga, known as the Battle of Bemis Heights, in which the rebels held firm and forced the British into retreat:

" ... and other Batle West of fremens ... on the hill and that Day Engaget with Canons But how many was killet at eithere Sit I can not say ... "

Afterwards the British attempted to retreat across the west bank of the Hudson but were blocked by General Gates and forced to march back towards the east and encamp on a hill north of the 'FishKill' and Saratoga. Burgoyne's army was weakened, wounded and surrounded. On October 17, 1777, he and his troops met General Horatio Gates at Saratoga and surrendered. Of the 5,800 men of the British army who lay down their arms that day, Lt. Henry Simmons and his men were among them.

" ... the Sam Day we wend as fare as arche menelas to cover the Artificers for to mack Briges and there we law two Days the 12th we wend Back agin to flying arme which lay on the hill north of the fish Kill and there we lay until the 17th and that Day we layt town our arms by Capitulation ..."


Obliged by the terms of surrender to return to Canada, many of the British and the American Tories who fought alongside them embarked on their long journey north, some by land, others by water. Simmons undertook his trip with 28 of his men"

" ... in the Convenon It was agreet that the Volunteer Saillors artyficirs batone men must go to Canada and so we Croset the Rever that Day and wend as far as Bathen Kill and the 18th to fort Johnson and the 20th to for Gorge."

From the Battenkill River to Fort George is 27 miles; according to Simmons' journal, the trip took three days. They continued their journey on board the sloop Demon Three and by a "butiaker" (thought by Dr. Burleigh to be a type of boat) further up the lake; they eventually made the rest of the journey to Fort Ticonderoga by foot:

"We Came on Dimon III and took a Butiacker and Came that Day to the nine Mile Iland ... and the 25th to Diante rogo."

The journal's transcriber, Dr. Burleigh, described the journey as "a most dispiriting time ... and a most distressing situation." Simmons and his men were travelling by bateau the last week of October in the face of a north wind blowing snow and rain. A typical bateau would have comfortably transported a crew and onboard party of 20 at one time, but Simmons was transporting half again as many. Forced by weather and changing winds to come ashore on more than one occasion, they eventually arrived at Split Rock, about three miles north of Ticonderoga:

"... there we gat a batone and wend that Day a boud 8 mile the Wind in the North and there we lay still in the woods and a Storm from the north With Snow and a little Rain ... and there we came about noon the wind Stle in the north it Rainth that afternoon and the next night the next Day the Wind came to the south and wend from thence the 29th as fare as Split Rock and there we lay wind bound."


Simmons and his men reached Point au Fer, New York, at the northern end of Lake Champlain a little more than a week after having left Ticonderoga by boat. They entered the Richelieu River, which drains Lake Champlain into the St. Lawrence, and eventually arrived at Fort St. Johns. They found no shelter at the former French fort and were forced to sleep in the woods during their first night in Canada. They were left with no choice but to continue travelling and headed west along the south shore of the St. Lawrence to Longueuil, across the river from the Island of Montreal:

" ... from thence five mile to the north of point to faire ... the 3th about noon we arift as Saint Johns and there we lay that night in the woods and we wend about nine miles there we layer with Some french men ... then the 6th we wend to Langgale."

After experiencing some difficulty at first, they managed to get across the river and found lodging for several nights on the island:

" ... the west Supbub of Montreal the 8th we wend up to Lachenne there we stayt that night the 9th we was billetet in the St. Suse."

At this point Simmons and his men had been gone from Claverack for almost four months, and from Saratoga for three weeks; they now found themselves in a foreign land almost 400 miles north of their homes. To pursue their Loyalist grants they were obligated to travel east to Quebec City, a journey of another 180 miles, which they completed in two weeks. There, Simmons' journal fell silent.

Of the 28 men who made the trek, one third were teenagers, 10 were in their twenties, four in their thirties; Simmons himself was 37 years old. In December 1783, the Loyalist corps was reduced and the land along the St. Lawrence and Cataraqui Rivers ordered surveyed in anticipation of their resettlement.

It took several years before the men received land grants and for their families to join them. In 1784 Lt. Simmons led more than 400 men, women and children to settle in Ernesttown County on the St. Lawrence River past Kingston and more than 150 miles west of Montreal. Of the 27 men who made the original trip from Claverack and later Saratoga, 11 chose to settle in the area. The men were granted land according to their rank and land administrators made efforts to provide each of the families with food, clothing, arms, tools and seed.

Simmons took 1,300 acres of land slightly north of the St. Lawrence and began improvements that included an inn and saw, flour, and feed mills. He harnessed the "Big Creek" and gave the nearby road its name: Simmons Mills. The community became known as Wilton--Henry Simmons' middle name--and Austin Simmons, his grandson, kept his mills in operation until the end of the 19th century.

As for his hometown on the Hudson River, Claverack was incorporated into the rapidly growing port city of Hudson, which came within one vote of becoming the state capital. In 1790, Hudson was the eighth largest city in the United States.

Simmons' commanding officer, Captain Christian Wehr, settled in the village of Philipsburg, Quebec, near the Vermont border, where he died in 1824 at the age of 92. Colonel Edward Jessup was awarded a land claim east of Kingston. There he founded the town of Prescott, Ontario, and "died of a palsy" in 1816 at the age of 80.

The final resting place and year of death of Lt. Henry Simmons are unknown. There is however conjecture that he is buried along the Big Creek in an unspecified location in the backyard of a property owned by a sixth generation descendant.

In commemoration of two significant Canadian anniversaries--Quebec City's 400th and the St. Lawrence Seaway's 50th this is the sixth in a series detailing the rich military history of those "shadow soldiers" who played a part in the development of Canada along the St. Lawrence corridor. Mark Jodoin credits the work of Dr. H.C. Burleigh and other UELAC archival material among his sources for this article.
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Author:Jodoin, Mark
Publication:Esprit de Corps
Geographic Code:1CANA
Date:Aug 1, 2008
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