The Jeremiah Bennett Clan:
The Days of the Desperados

One morning in 1876, a Ridgefield man was sitting in a dining room of a Philadelphia hotel and was served a cup of coffee. As the man picked up a silver spoon to stir some sugar into his coffee, he did a double take. The spoon bore the man’s own name.

He sought out the hotel manager who explained that he had just recently purchased a group of similar spoons from a Philadelphia man.

That evening the Ridgefielder received a letter from home, saying that his house had been recently burglarized and that suspects in the case had been caught. Found in the possession of the thieves was a letter from their brother in Philadelphia, reporting “Goods received all right and disposed of.”

The Ridgefield visitor was just one of dozens of victims of  “the notorious Bennett family,” a Ridgefield clan that became the center of a sensational 19th Century crime spree that made hundreds of headlines in newspapers throughout the Northeast. 

 Despite their ancient and respectable roots, members of the Jerry Bennett family were accused of breaking into houses, businesses, and even train stations, generating “terror” in the hearts of townspeople while amassing a trove of stolen goods in their house and barn on Silver Spring Road.

It was a tale of bold crimes and strange events like no other in Ridgefield’s three centuries.

Jeremiah and Adeline Bennett and five of their sons lived in a small house a quarter mile south of the West Lane Schoolhouse in the mid-19th Century. By the time the crime spree was over, Jerry, Adeline, and four of their eight children had been arrested and jailed. Three Bennetts wound up spending years in prison.

Born in Ridgefield in 1821, Jerry Bennett was descended from the same family that had come from Fairfield to Ridgefield in 1721 and settled what is now the Bennett’s Farm region of town. His great grandfather, Trowbridge, fought in the Revolution and his father, Daniel, served in the War of 1812. By 1850, he had a small, 25-acre farm adjoining the south side of his father’s spread.

Jerry seemed like just another Ridgefield farmer. Like many other residents of the West Lane district, he made extra money as a shoemaker, a trade his father also engaged in. He seemed a conscientious citizen — in 1855, he found a stray horse, “blind of the left eye, lame on the right fore leg,” and paid for an ad in the Norwalk Gazette to find the owner. 

In July 1869 his wife Adeline, a year older than he, won three prizes in the Ridgefield Floral Society’s exhibit, including $2 first place awards for Best Bouquet of Mixed Flowers and Best Collection of Pot Plants.  Other winners were well-placed women in Ridgefield’s small-town society.

Signs that something was amiss about  Jerry Bennett first appeared, not in the dozens of newspapers that would later cover his exploits, but in the diary of a neighborhood farmer. 

Jared Nash, who lived on Silver Spring Road about a mile south of the Bennetts, kept a record of his daily life and on Feb. 8, 1865, he wrote down that  his constable father, Charles Nash,  had “to go up to court tomorrow to take up J. Bennett for cutting hooppoles.” Bennett had apparently been arrested for sneaking onto someone’s property, cutting down and stealing young trees to turn into  hoop poles. The sticks were sold for a variety of purposes, including making barrels and fashionable women’s skirts. 

Ten years later, all hell broke loose.

On July 21, 1876, Jerry Bennett, then 47, was arrested along with his wife, Adeline, 48, and two sons, James Mortimer, 18, and Francis “Frank” Bennett, 16. They were all charged with being involved in the rash of burglaries and larcenies that had been occurring in recent months.

However,  two other sons — George, 23, and Arthur, 20 — had escaped arrest and were believed hiding somewhere deep in the Silver Spring Swamp.  The Ridgefield Press, founded only a year and a half earlier, covered the arrests in a lengthy story under the biggest headline it had ever printed: 

A CENTENNIAL 

BURGLAR HUNT 

It was, of course, the year of the nation’s 100th birthday, though one would be hard-pressed to explain how that fact related to the Bennett gang.

“Citizens Turn Out in a Body and Search an Extensive Swamp for the Desperadoes,” the headline continued. 

The story explained that “for several years our village has suffered severely from burglars. Houses were entered both day and night, [and] robbed. Every one looked with suspicion toward a certain family but none dared to accuse.” 

However, The Press continued, “during the past year robberies have been almost [a] daily occurrence. People began to talk publicly about certain parties and express their opinions more freely. Several fruitless attempts were made to ferret out the rendezvous of the burglars.”

As “things were coming to a crisis, spies were sent to watch Mr. Jeremiah Bennett’s house and ascertain the hiding place of his sons who lived in the woods. For a while, all efforts were unsuccessful; but finally a cave was discovered. Nothing by way of proof was found.”

A local “Anti-Thieving Association” was formed and offered a $50 reward. That sparked the interest of a detective from New York State, and his investigations led to the arrests of Jerry, Adeline and the two sons. But it was George and Arthur Bennett who, with their father, were suspected of being the main culprits. 

That Sunday, the day after the arrests, “nearly every able-bodied man” in Ridgefield responded to a call from Ridgefield Constable John Gilbert to mount a massive search of Silver Spring Swamp for George and Arthur. 

“Guns were aplenty, pistols numerous,” The Press said. “It was a motley but courageous crowd.”

The search began around 5 o’clock Sunday afternoon. “The ‘chosen brave’ entered, determined to succeed or perish… Now and then a false alarm was given which caused no little excitement. At every sound, each one grasped his firepiece more firmly and peered into the bushes.”

Alas, when the hunters emerged from the swamp near sunset, “no one had discovered the slightest trace of the thieves. Our ‘chosen brave’ were in a pitiful plight. Some of them had been immersed in slough holes, others had been lacerated by briars and thorns.”

Meanwhile, a search of the Bennett house and barn had uncovered “large quantities of stolen goods,” reported the Hartford Courant. They included “accordions, fiddles, watches, finger-rings, bracelets, diamond pins, boxes of perfumery, guns, gold and silver thimbles, watch-chains, clothing, handkerchiefs, and several other things of value. One accordion was found in a stone pot in the milk-room, and the other and the box of perfumery were found in a box of bran up stairs.”

On Monday townspeople showed up to claim many of the recovered goods, including representatives of the Bailey and Gage Store (now the Aldrich Museum’s upstairs offices) who later went so far as to get local legislators to file a bill in the State Legislature, compensating them for their losses.

Jerry and Adeline, with sons Mortimer and Francis, were arraigned in Danbury that day and held in jail under bonds totalling $4,800 — nearly $120,000 today. All pleaded not guilty.

In court Jerry proposed something rather unusual. He would help in the capture of George and Arthur because “he felt sure their appearance would clear him,”  The Press reported. 

The capture would happen in a rather odd way. 

“The constable was to take Mortimer down to the edge of the swamp, where the other sons were supposed to be concealed, and he was to whistle them out,” The Press revealed. 

“The ‘chosen brave’ were again called for, and with alacrity did they respond. Sixty long minutes were spent on the edge of that swamp with nothing to relieve the monotony but Mortimer’s decoying whistle. It was no use; those boys were not to be whistled from their haunts. They knew the ‘chosen brave’ were lying in the bushes.”

Newspapers far and wide reported the goings on in Ridgefield, often rather colorfully. An account in the Washington (D.C.) Evening Star described the “two more sons still at large, but a force of men are looking for them, and have driven them into an almost impenetrable swamp southwest of the village where it is believed the brothers have a burrow.”

By Wednesday that week in August, people who lived along the fringes of Silver Spring Swamp were reporting chickens stolen, potatoes dug up and even cows milked by unknown hands. Then someone said he’d spotted George and Arthur. 

Constable Gilbert organized yet another hunt, this one more massive than the first.

“Every man that could be found was notified and requested to put in an appearance at the West Lane School House on Thursday morning at 8 o’clock to receive orders and information of the plan of operations,” The Press reported.

By 9 a.m. between 300 and 400 men — including contingents from Wilton and South Salem — had gathered at the corner near the schoolhouse. 

“Each man carried at least one fire-piece — and such a variety!” the newspaper exclaimed. “Some were armed with weapons that did service — and from their appearance, plenty of it — during the Revolutionary War!”

Under Constable Gilbert’s leadership, the mob — members spaced four feet apart — entered the north end of the swamp and began to move south.

It was no easy trek. “Before they had advanced one rod, Constable Gilbert sunk into the mud so deep that the top button of his vest only was visible,” The Press said. 

Others had similar problems but the searchers pressed on  through muck and thick underbrush. 

“They had gone but a short distance when a trail was discovered which led to a place where the fugitives had done their cooking. By and by, a valise was found and passed from one to the other until it reached the margin. It contained nothing, but was recognized as being one of the three taken from Wilton station.”

After four hours of searching, “it was evident that they had evacuated that swamp. The woods were then searched, but with the same result. Many of the scouts were getting tired and hungry, and the search was for the time relinquished.”

About 100 searchers remained, however, and after lunch looked for the caves that the boys had occupied. “Three caves were found which showed signs of recent habitation,” The Press said. “They were all small — the largest one being about eight feet long, four feet wide, and five feet high. After this examination, further search was abandoned.” 

“The boys”  remained on the loose and still very active.

On Thursday,  Aug. 10, they were spotted with stolen butter and a kettle along the tracks near the Cannon Station in Wilton. They dropped the goods and fled into the woods.

On Friday,  they broke into Elmer Olmsted’s shirt factory in Wilton and stole all the cash. “Mr. Olmsted pursued them, armed with a seven shooter, and they dropped their plunder,” reported The Courant. “He had a good chance to fire at them, but was afraid to do so.” 

The Courant added with some apparent amazement, “It is reported that on Tuesday night, they visited a hotel in Danbury and called for Schenck beer. They were recognized, but allowed to depart in peace.”

 The following Monday night, they broke into the Bailey and Gage Store once again. First they first stole a ladder from the King estate barn across Main Street. They used the ladder to reach a second-story window at the north end of the store where they removed a pane of glass to gain entry — why they bothered with a difficult, second-story entrance when there were plenty of first-floor windows is unclear. They stole guns, ammunition, knives, and cigars, as well as gold pens, gloves, clothing, pocket-books, and even perfume.

The fledgling Ridgefield Press attempted to express the community’s outrage and frustration. “Is it not in the power of the authorities to discover the guilty parties and bring them to trial and well-deserved punishment, thus putting a stop to such nefarious proceedings, of which there have been too many recently in this vicinity?” the  newspaper asked on Aug. 16.

Apparently to avoid the increasing heat in and about Ridgefield, the Bennett brothers then headed west to the Hudson River Valley. However, they were tracked down and, on Monday, Aug. 21,  Arthur gave up — in a rather bizarre fashion.  Another member of the Bennett family, Henry Bennett, 28, a brother who lived in Peekskill, N.Y.,  and was five years older than Arthur, handed Arthur over to a Peekskill police officer, stating “that he brought him there for the purpose of giving him into custody and claiming the reward of $100,” The Press reported. “Arthur made no objection to the arrest and quietly accompanied the officer.”

It sounded as if Arthur had had enough of being on the run. He knew the rest of the family was in trouble, and may have believed that he would be able to help financially by letting brother Henry collect the reward money for his capture.

Peekskill authorities telegraphed Constable J.H. Barlow in Ridgefield who came and took Arthur to the Bridgeport Jail.

Then, the following day, George Bennett was spotted at Fort Montgomery, a village across the Hudson River  from Poughkeepsie, where he was peddling “small notions and passing by the name of Smith.” He had camped at Cronk’s Cove, along the edge of the river, and was expected there again that night. Constables and local officers set up an ambush and captured him at the cove when he arrived. He was rowed across the Hudson, taken to Peekskill down river, and then to Bridgeport Jail.

All six Bennett suspects were behind bars in Bridgeport. 

Justice was more swift in those days, and the trials took place in early September.

“They are very respectable looking people, and are the last who would be suspected of crime,” said a brief account of the proceedings in the Bridgeport Standard.

A jury found half the clan guilty of burglary and theft. Jerry Bennett got five years in the state prison, and George and Arthur each got 15 years. 

The jury found Adeline not guilty, saying that “she acted jointly with and under the influence of her husband, and that the criminal intent was lacking.” James Mortimer was found guilty on a single count, but since the goods were valued at less than $15, he escaped a prison sentence. Charges against Francis were nolled (not prosecuted), perhaps because he was only 16 years old.

Although free again, Adeline and her two sons were still in trouble. Many claims were being filed against the Bennetts’ property in an attempt to recoup losses suffered by people who were burglarized and whose goods had been fenced. 

Indeed, two weeks after the trial, Henry Bennett appeared before the Ridgefield Board of Selectmen, seeking the $100 reward for turning in his brother. “He satisfied the authorities as to the correctness of his claim, and they paid him the money,”  The Press said. Henry probably used the reward — worth nearly $2,500 today — to help his mother and brothers who were in dire financial straits.

By January, Probate Judge Hiram K. Scott had declared Jeremiah Bennett an “insolvent and assigned debtor” and that anyone with claims against the Bennett estate had three months to file a notice with the court. To pay off at least some of the debts, the property was sold.

The three convicts were all sent to the state prison at Wethersfield, a sprawling complex that held nearly 500 prisoners. The 1880 census reveals a somewhat touching situation, however:  Both Jerry and George, father and son, were working together in the prison’s shoe shop.

By 1886, the New Haven Register was reporting that George had undergone treatment for “very peculiar delusions.” One of them was that “at night he could pass out through the keyhole in his cell and go anywhere in the state, but that the moment anyone to whom he appeared touched his body, he would disappear and instantly be back in his cell at the prison.”

The Register said “he would not, when examined, hear any disbelief of this notion  and offered to prove his story by appearing some night to Dr. Packard or Dr. Root.”

The doctors eventually used “a most plausible reasoning” to finally convince George that what he experienced was a delusion.

Arthur Bennett was apparently a model prisoner and in July 1888, was paroled by the Board of Pardons. “Arthur, in his statement before the board, said he pleaded guilty to save his father,” reported the Waterbury Evening Democrat. The paper added that the prisoner “shows the effects of his long imprisonment.”

Arthur indicated he would probably join his mother, Adeline, who was then living in Philadelphia. After the trial and loss of the family farm, Adeline may have gone to Philadelphia to live with her oldest son, Seth, who was a shoemaker in that city. It may have been Seth who had sold the spoons to the hotel operator, perhaps unaware that they were stolen.

It is not known whether Jerry and Adeline ever saw one another after the trial. Sometime after he was released from prison around 1881, Jerry Bennett went to live with yet another son, John S. Bennett, a shoemaker, and his family, in Syracuse, N.Y. In the 1900 census, Jeremiah Bennett was described as a widower and a shoemaker. 

A year later, Jerry died in Syracuse at the age of 80.

Whatever happened to Adeline and her sons has not been discovered. All quickly left Ridgefield — either as prisoners or as debtors — and probably would have liked to forget their old home town and what happened here in 1876. The townspeople likely felt the same way about them.