Chester County Prison is located approximately 10 miles south of Chester County's seat, West Chester, Pennsylvania. The current prison was opened in 1959, and operated under the original construction until 1983 when parts of the prison under went renovations and expansion and in 1993 a new Pre-Release / Work Release Center was constructed on prison property. The current structure is one of only four such buildings used as the county jail since Chester County was incorporated by William Penn in 1682, as one of the three original Counties. Chester County's 1st jail cells were built in 1786, and were located in the rear of the Courthouse. Prior to 1786, the County House of Correction and Work-House was located in Chester, Pennsylvania (former County Seat).

In 1839, the County of Chester built it's 1st off site jail at Market and New Street in West Chester, Pennsylvania. This structure subsequently under went alteration and additions up until 1941. This Prison was modeled after the Walnut Street jail in Philadelphia the 1st County institution which was built in 1770. The only differences were the sanitary provisions, beds and heating for each cell. In July 1951, the County of Chester realized that major steps were needed in correcting some of the worn out features in the 1839 jail. After an extensive survey of the building by architects it was established that the building was in poor condition and was declared unsafe by the Department of Labor and Industry.

Architects were then asked to provide alternatives to the County Commissioners to make some kind of future projection for the renewal of the county jail. The County Commissioners explored prisoner population growth, site locations and costs during the years of 1952 through 1954. In 1954, pressure intensified when Grand Juries calling on some kind of action to be taken on the part of Chester County to rectify the unsafe conditions at it's jail. During the studies between 1952 through 1954 it was determined that remodeling or rebuilding in the heart of West Chester was not justifiable due to lack of space. The County Commissioners formed a committee in November of 1954, to make a survey of alternative locations for the new jail.

In May of 1955, the committee recommended that the new prison be constructed on the land owned by the County Institutional District adjacent to the County Home in Pocopson, with the intent of developing a prison farm. In the fall of 1955, extensive studies were conducted to determine if the property would be adequate to support such a facility. The studies also included research on preliminary plans and specifications for a new prison.

In February 1956, the architects reported to the Commissioners on the recommendations for the capacity of the new prison. These recommendations were in accordance with a study projecting the growth of the county up until the year 1965. The recommended prison capacity was a figure of 142 individual cells. These cells were broken down into 72 minimum security cells, 48 medium security cells, 10 maximum security cells, and 12 female cells for a total prisoner capacity of 142. The recommendation made by the Architects to the Commissioners were viewed by the Judges as being ultra conservative. They felt that if proper security facilities were provided in the new prison many of those prisoners previously sentenced to the State Penitentiary would be sentenced to the County Prison. The Commissioners further decided that the assumption of 1965, as the point of saturation population wise was working too close for comfort. They suggested that the population figure be extended to 1970. The Commissioners also took into account the modern train of thought that insisted upon rehabilitation programs for the prisoners that would provide classrooms for academic education, shops for vocational training, and facilities for psychiatric analysis and therapy. The County Commissioners had to determine what would be considered reasonable and reachable for a county jail. They also had to distinguish a clear division that would decide the responsibilities of a county prison versus a state penitentiary. It was determined that the length of sentence would decide what was reasonable for the county jail and its role and responsibility in such programs. The Commissioners therefore decided that the 23 month sentence, which often was commuted to something less, would become the pivotal point short of which an extensive rehabilitative program would not be necessary. Although various aspects of this subject were explored, it was determined that the new County Prison would have shops, facilities for rug weaving, chair caning and similar simple occupations, along with the operation of the kitchen, cannery, laundry, and maintenance services around the prison, for those prisoners not fitted or adjusted to work on the farm or throughout the community. This policy would, with certain exception, prevent the gradual glutting of large segments of cells with a rigid population of long term prisoners for which it is not intended, or equipped.

The concern and reluctance of both the Commissioners and Architects was not to overbuild the prison facilities but were appreciative of the foresight express by the Judges in their insistence upon the general increase in the number of cells needed. It was decided that the boiler room, kitchen, dining room, and etc. were to be built adequately so that they could handle future expansion. It was also decided that the term minimum security was to be dropped because it was equated with dormitory living areas and for the times this was not condoned by the Pennsylvania Penal Code. This all led to the cells being designed for individual confinement with the exception of the infirmary ward. Therefore the term medium and maximum security was adopted for Chester County Farms.

The prison was comprised of two basic cell types. The 1st was the maximum security unit which was built with two rows of cells back to back with a access chase to the plumbing between the two rows. The two rows would have separate corridors so that the prisoners cannot see or communicate with each other. The windows for the wing would be high up in the exterior wall away from the cells and on level of the upper tier. The 2nd type was the medium security wings which was to have a central corridor with the cells on both sides facing each other and with security windows in each cell on the outside walls.

The scheduled construction of the 1959 prison was comprised of 128 medium security cells, 24 maximum security cells, 15 female cells, and 4 juveniles cells for a total population of 171 individual cells. In addition to the general population cells there were 2 restraint cells and 2 treatment cells in the maximum security unit for men. There were also plans for 1 restraint cell and 1 treatment cell for women. The prison also had 4 single cells and a large holding cell in connection with the admissions area as well as plans for a 5 to 6 bed infirmary for men and a 2 to 3 bed infirmary for women. These plans were approved by the Judges as minimum requirements and that only because of the flexibility of the plan to support future expansion. The County Commissioners also approved the program along with the preliminary plans, outlined specifications and the budget for the new prison after the presentation of the Citizens Prison Survey Committee, the Pennsylvania Prison Society, the Prison Board, and the Commissioners of Corrections of the Commonwealth of Pennsylvania. The Architects then were authorized to proceed with the contract drawings and specifications. The Dedication of the 1959 prison was conducted on January 14, 1959, at 2 p.m. and it has subsequently been in operation ever since.