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Jennings Trail is named in honor of Bessie Jennings. Her family settled in this area around 1650.

A beloved educator and authority on Westport’s past, she originated and led tours of local historic sites, for decades of elementary school students.

Conceived in 1974 as part of Westport’s plans to celebrate the Bicentennial, the Trail was initiated by the Westport Historical Society in collaboration with the Westport Young Woman’s League.

23 markers were installed throughout Westport. Jennings Trail is now under the stewardship of the Westport Historic District Commission.

Four additional markers are now being added. Historian Morley Boyd explores the story behind the most recent one.

At 1 a.m. on Saturday, April 26, 1777, the Meeker household was wide awake.

Thirty-six-year-old Benjamin Meeker stared out the window at a scene that would have defied description. On the narrow, muddy road beside the Meekers’ 50-year-old Cross Highway residence, a heavily armed force from one of the most powerful nations on the planet came into view.

Suddenly there was shouting. The column of 1,850 soldiers – stretching into the darkness for nearly a mile – halted in front of Benjamin’s house.

The expedition was under the command of British Major General William Tryon. Three regiments had participated in the battles of Lexington and Concord. One had been at the Battle of Bunker Hill. These were seasoned professionals.

The “Meeker house” in the 1930s. After the Revolutionary War, Benjamin Meeker built the barn in back. It, and the house, still stand.

Benjamin probably knew that, around 5 p.m. the previous afternoon, a dozen British transports and 3 warships had arrived at the mouth of the Saugatuck River.

Because it had taken 6 hours to get the men and materiel off the ships and assembled, there was time for word to spread. Although the Americans had previously received intelligence that the British — desperate for food, tents and other supplies — likely intended to capture the Continental supply depot in Danbury, no one in those early hours could be completely sure of the enemy’s true plans.

The British had no idea how to get to Danbury, but they were guided by men who did. They also knew the loyalties of every resident in every house along the way.

Though we don’t know the scope of Benjamin Meeker’s efforts during the Revolutionary War, documents and testimony indicate he was a patriot. He would have particular concern about the force now standing outside his house.

After the order was given to halt, there was likely a knock at the door. When there was no response, someone probably started calling for Benjamin.

When that did not have the intended result, a British Regular was ordered to fire his weapon at the heavy plank door. The musket ball imbedded itself, but did not pierce it.

The door today. The hole left by the missing musket ball can be seen on the left side, underneath the knocker.

Benjamin faced a decision. If he continued to resist, his house would likely be set ablaze. Or perhaps the artillerymen would be ordered to open fire on the residence.

Either way, Benjamin knew that continued resistance could put his wife Abigail and their children – Anna, age 10; Sillivant, 8; Rachel, 3, and Benjamin Jr., less than 1 month – in mortal danger.

He opened the door, and was arrested. His older brother Daniel, a sergeant in the local militia, was arrested too.

Though Tryon had issued explicit, written orders forbidding plundering during the expedition, the house was ransacked. The family’s livestock were slaughtered. This kind of treatment (and worse) by British forces was typical near the coast in what is now Westport.

After Benjamin and Daniel were made prisoners, the column resumed its march. Arriving in Danbury the next day, things did not go as planned.

Although the original objective was to carry off everything possible from the Continental supply depot, Tryon’s men could not secure wagons to do so.

British forces landed at Compo Beach, marched to Danbury, headed back south and — after the Battle of Compo Hill — retreated to Long Island.

Then came word that American forces were rapidly closing in on the British position. Perhaps even worse was news that Benedict Arnold was among the 3 American generals  preparing to challenge the British, as they attempted to return to their ships at the mouth of the Saugatuck River.

Though Arnold was a pharmacist by trade with no formal military training, he was feared by the British for good reason: In the first 2 years of the war, he had proved to be a brilliant tactician, with astonishing endurance.

With time running out, the British decided to destroy the Continental supplies and get out of Danbury.

Presumably, Benjamin and Daniel Meeker — joined by over 50 other American prisoners — not only witnessed what happened at Danbury, but were dragged along on the harrowing retreat back to Compo.

Exhausted, out of ammunition and pinned down at Compo by American forces, only a do-or-die fixed bayonet charge got the British expedition back to the safety of their ships.

Robert Lambdin’s “The British Landing at Cedar Point, April 25, 1777,” 1955 painting is now part of the Westport Permanent Art Collections.

Although it’s impossible to imagine what the previous 48 hours must have been like for Benjamin, Daniel and the other American prisoners captured along the way, their situation soon got  much worse.

As Abigail Meeker watched her arrested husband and brother-in-law disappear into the night, she knew their chances of returning alive were slim.

It has been said that British-occupied New York was more of a gulag than a garrison. After the British filled the debtors’ prison with rebels, they turned the city’s non-Anglican churches into cages. When those exceeded capacity, prisoners were packed into New York’s massive, multi-story sugar warehouses. Finally, 16 decommissioned ships floating off Brooklyn were used to hold American prisoners.

It was a nightmare of brutality, starvation, disease and death. Over half of the estimated 18,000 American prisoners did not make it out alive.

Both Meeker brothers were thrown into a sugar house prison. They managed to survive for 18 months. before being released as part of a prisoner exchange.

The men returned to their families. Life resumed as best it could. When Daniel died 6 years later at age 45, his wife Abby interred him in the Lower Green’s Farms Burying Ground (now the corner of Greens Farms Road and the Sherwood Island Connector).

Daniel Meeker’s headstone.

Benjamin supported the family of his younger brother Stephen, who had just been killed in action in Pennsylvania. He also supported his younger sister Molly, whose husband was badly wounded during the Battle of Stony Point. Benjamin died in 1817, at 75. When the ground thawed that spring, his wife buried him the Green’s Farms Church’s Upper Cemetery.

The Meeker homestead still stands at 188 Cross Highway, bearing silent witness to those who bravely fought for America’s independence.

(Hat tip: Bob Liftig. For a 2015 “06880” story on the musket ball embedded in the Meekers’ door, click here.)

(“06880” regularly covers Westport history. If you enjoy stories like these, please click here to support our work. Thank you!)

The Minute Man Monument commemorates the Battle of Compo Hill. It took place 3 days after the British marched past the Meekers’ Cross Highway home. (Photo/John Maloney)