A Brief History of the Middlesex County Gaol at Haddam

Middlesex County was formed in 1785 from towns that had previously been part of Hartford and New London Counties including Middletown, Haddam, East Haddam, Killingworth, Saybrook, and Chatham (Durham joined in 1799). It is believed that Haddam and Middletown were designated ‘half-shire’ towns to share the county seat because of their central location. Each town was required to erect a courthouse and jail/workhouse in order to carry out their responsibilities as a half-shire town. Middletown erected a series of jail buildings which served as temporary quarters for prisoners convicted of minor crimes, while Haddam was the county’s principal jail.

With the arrival of the County Court House, Jail and the opening of the Middlesex Turnpike in 1802, the village of Haddam experienced unprecedented growth and became a regional commercial and institutional center. Merchants, craftsmen, innkeepers and professionals established themselves along the turnpike near the jail and courthouse and transformed the town from a “closed” tight knit community to a thriving “cosmopolitan” center.

Middlesex County Court System

Superior Court was to be held in Middletown on the last Tuesday of July and in Haddam the last Tuesday of January. The Court of Common Pleas would meet in Middletown on the second Tuesday of December and in Haddam on the fourth Tuesday in April. This arrangement continued until 1855 when the County Court was abolished and two additional terms of Superior Court were established.

The judges of the county courts and the justices of the peace along with the county commissioners created the Civil Authority of the county and were empowered to levy taxes and to otherwise supervise the construction of the courthouses and jails. Maintenance of the buildings was supported by taxes and subscriptions county wide. In 1836 the county authorities decided not to levy a direct tax to support the county buildings but using tax lists apportioned the costs “among the towns of Middlesex County.” This left it up to the town to raise the money and eliminated the county tax. This hidden tax was added to citizen’s local tax bill.

For over a hundred years there were continuous campaigns and discussions about the necessity of have two jails and two courts in Middlesex County. Middletown authorities relentlessly tried to have the jail and court moved solely to their city and other Middlesex County towns such as Saybrook campaigned to have the court moved to their communities. There were a number of times when the County officials determined that only one courthouse and jail were needed but never acted on the conclusion Somehow through political pull Haddam was able to hold on to the prestigious honor of having the courthouse and jail which brought economic benefits to town as well as the distinction of being the county seat.

The County Courthouse in Haddam tried cases that were county-wide and brought many people to town including judges, lawyers, witnesses, jurors, and other parties in the case. Most of the cases revolved around settling property conflicts, defaults on contracts, for damages or to recover bad debits. Occasionally there were more infamous trials like the murder. The Courthouse stood at the intersection of Walkley Hill Road and Saybrook Road and burned in 1929. The site is now know known as “Courthouse Green”.


Prisons were the chief places to house criminals. In the late 18th and 19th centuries, criminals in Middlesex County included not only those who were convicted of serious criminal acts such as murder, burglary, and malicious injury but those who were committed for adultery, keeping a house of ill-fame, trespassing on railroad property and neglect of family. Records show that most prisoners held at Haddam were imprisoned for breach of peace, drunkenness, vagrancy, and larceny. The State of Connecticut had a State Prison for criminals sentenced to hard labor and for very serious crimes. The first was New Gate Prison in Granby which operated from 1773 to 1827 when it was replaced by the Wethersfield State Prison. Wethersfield operated until 1963 when all inmates were transferred to the new prison in Somers. The County Jail was primarily used to house criminals convicted of lesser crimes or those awaiting trial.

In 1837 the state of CT passed an act which permitted counties to require prisoners after conviction to be put to work, according to their strength and ability. The sheriff of the county was designated the keeper of the jail. A deputy jailer was to be in charge of the labor and would provide prisoners with food, clothing, tools, materials and health care when sick. The deputy jailer was also acting as purchasing agent and sales agent for the jail. This allowed prisoners being held for fine and costs only to pay off their debt by labor. In 1845 the State of CT gave the county commissioners the right to hire a chaplain or religious instructor to be paid out of the net profit.

Early prisoners housed in the Haddam Jail worked various jobs including helping out on local farms and industry. It is recorded prisoners were responsible for erecting the additions to the jail itself saving the town a considerable amount of money. By the early 20th century the Haddam Jail had established its own dairy and farm which provided prisoners with full time employment. The farm and dairy provided food for the prison, local Temporary Children’s Home and to sell. The institution was said to be self-sufficient and grew vegetables and raised pigs, cows and chickens. The jail actively farmed until 1964-65. In 1914 feldspar was discovered on the Jail property and prisoners were employed to quarry the stone which was sold to out-of-state firms.

The jail grounds were never enclosed and there were many successful escapes because of the lack of security and small staff. Prisoners frequently just walked away and would jump a train or hitch a ride out of town. Some long time residents recall the Haddam Jail as being called a country club and prisoners described as “guests.” Many criminals were “vagabonds” who needed a warm place to stay during the winter and would find a way to get themselves arrested so they would have a shelter and hot food. Prisoners would play baseball on the grounds, take picnics to the Connecticut River and even visit local restaurants and inmates could bring there own bedding and food was allowed to be delivered from home.

Most of the prisoners held at the Haddam Gaol were incarcerated for lesser crimes such as being drunk and disorderly, petty theft and brawling. There were also men and women held for committing murder including the infamous Emil Schutte of the Cremation Hill fame. In 1911 alone there were nine people at Haddam awaiting trial for murder including four men accused of causing a train wreck in which one person died. There were marriages and births at the jail as well as stories of corruption.

Jail in Haddam

The first Gaol in Haddam was built of wood and was located on a lot on the south of intersection of “the road to the woods” (currently known as Jail Hill Road) and Middlesex Turnpike (now Saybrook Road). Within a year the Civil Authority was calling for an addition to the jail and noted for the first of many times that maybe only one jail was necessary for the county. Not much is known about the early jail building.

In 1812, the first jail building was condemned and a replacement was constructed on the same site. Written histories indicate that the second jail was one story wooden building measuring 24’ x 30’. It featured small window openings with iron bars. After it was no longer used as a jail it served as a storehouse of crops grown by the prisoners including cabbages and turnips.

By 1843 it was determined by county authorities that the Gaols and Workhouses in both towns needed to be replaced. After considerable debate a tax was finally was passed to build a new jail in Haddam, much to the dismay of Middletown residents.

In 1845, a stone cellblock was created on the north side of the intersection to house criminals, the insane and debtors, and the sheriff’s family. Samuel, Isaac and Jonathan Arnold were hired as general contractors for the building. All three were active in civic affairs, operating a shipping company, a quarry and lumber business as well as serving as selectmen, constables, justices of the peace and legislators. The Arnolds provided all the raw material for the jail including stone from their quarry. It is said that labor was done in part by the prisoners.

The Specifications of the Middlesex County Prison, Haddam, Ct., delineate the materials to be used to construct the jail and workhouse, and the “mansion” built to house the sheriff, his family, and women prisoners. The keepers mansion measured 37 x 28 feet and was believed to be larger than any other private home in Haddam. The second floor was to be used to house debtors and the female prisoners. The specifications outline requirements for the Keepers dwelling, plastering, glazing, doors, papering, stair railing, and prison. The prison design called for stone laid in strong mortar with 2 feet thick along the cells and 15 inches thick against the hall. The front of the cells was to be 12 inches thick of stone or strong brick laid solid with strong mortar. The specifications even detail the “orrifice for food”. The roof was to be covered with first quality tin, laid with a so termed standing edge and covered with three good coats of Venetian red oil paint. The “Statement of Expenses of Building the Goal and Workhouse at Haddam” totaled $9,145.83. A wooden workhouse and a barn were built by the Arnold brothers in 1855.

In 1878 a Second Empire style granite addition was added as housing for the women prisoners and the jailer’s family, as well as expanded spaces for his administrative duties. With managerial facilities moved to the new section, more jail cells were added within the older building. Unfortunately, the location of specifications for the mansard roofed addition is not known.

Newspaper articles written between the years 1899 and 1939 attest to the ongoing maintenance of the building. In 1899 bathtubs, plumbing and “a heating apparatus” were scheduled to be installed. Night buckets were still used in the women’ cells in the early 20th century. The plumbing in the rest of the building was described as “good.” The use of kerosene lamps was a cause of concern, as was overall ventilation.

In 1939 there were three toilets, one urinal and one shower in the men’s section. Benches were provided for men who ate in the cell block. The floor was described as loose and unsafe. The four women’s cells were on the second floor behind the sheriffs quarters. The area was described as “poorly ventilated. The windows at the left end of the corridor being small and the door leading to the back being set in such a way that no air can circulate.” The report concludes that the sheriff does not have the staff or money to upgrade facility.


A comparison of the costs of the Haddam jail in 1932 compared to the Tolland and Litchfield prisons, which had similar numbers of internees, shows that the Haddam sheriff was paid less. The Haddam jail had, in addition to the sheriff, a matron, and a deputy jailer who was also the farm superintendent. The Litchfield sheriff had, in addition, a clerk, four guards and a chaplain. Haddam’s Sheriff Thompson complained that the county could spend thousands of dollars on sheets alone because the prisoners “take no care of them, but rip them to shreds, either in anger or because they want a section for a bandage and don’t want to call the doctor available to them. Living conditions at the jail were criticized by a few prisoners who were regularly sentenced there for drunkenness. In a newspaper interview, the jailer stated, “a talk with prisoners who have seen the insides of jails in other sections of the country brings out the fact that the county lockup is a paradise compared to most.”

In the 1890s, Haddam lost its position as county seat, and the court moved permanently to Middletown; however prisoners were still housed in Haddam. By this time the only prisoners held here were those awaiting trial or serving sentences less than one year. Reports state that a major remodeling was done in 1955 for a cost of $250,000. This included new cell blocks, visiting room, guard’s office and kitchen. In 1960 when the county government was abolished the ownership of the property went to the state. In 1964 another smaller remodeling job was completed and consisted of a new dining area to accommodate 64 prisoners. Prior to the expansion prisoners ate in their cells or cell block.

Modern Uses

The jail remained active until 1969 when inmates from all the county jails were moved to the state prison. When the building closed one editorial stated “there was a certain humanity about the Haddam Jail…it may not have been a wholly pleasant for the involuntary inhabitants…there were fringe benefits including working in the dairy barn, the fields or in the gardens. It became known as the “the Country Club.”

The following year the building became the Correctional Academy, and was later renamed the Connecticut Justice Academy. It was used in the 1970s and 80s as a simulated lockup for prison guards who were treated like criminals. They were strip searched, fingerprinted and put in prison clothes before being incarcerated for a weekend. For the following three weeks they lived in the cellblock which became their dormitory. The rooms which had been used by the jailer for his office and his family’s living space became a lounge, classrooms and a library. The barn was transformed into additional classrooms.

In 2007 the Town of Haddam acquired the building and surrounding 51 acres from the State of Connecticut. A jail advisory committee has been set up to work on the stabilization, restoration and adaptive re-use of the property.