This question has arisen many times and I will endeavor to answer with the information I have gleaned from my research of the archives and conversations with others who have a recollection of Pittsford's Past.
The first site of a jail was at the house that is located at the corner of South and State Streets - Number 35 State Street. The original home, built about 1850, was the small brick square home; the additions in the rear, located on South Street were added at a much later time.
John and Esther Brown lived in the home and were the "jailers", if you will. John was born in 1809 and came to Pittsford sometime around 1840. He and Esther were married about 1838 and we don't know if that was in Pittsford or in the town from which they came to this community and the census records in the historian's office do not indicate that place.
John and Esther ran a store from that small home. It was just one of the "businesses" which occurred in that home. The Browns became the "Poor Masters" of Pittsford and in this position; they were obliged to feed any person who might come to their door asking for a meal for which they paid twenty-five cents.
Any miscreant, who had been arrested by the constable and had been sentenced to spend some time in jail, was led to the basement of the home and incarcerated there. I understand that a fireplace and iron rings were still visible in the bricks of the foundation walls. (I have not seen them; I only report what has been told to me.)
John Brown, a merchant by trade, was also familiar with the craft of making barrels and so he ran a cooperage from that house, as well as the store, the poorhouse, and the jail.
He and Esther had at least one son, David, and they all lived in the rooms on the upper floor. So, at one time the house was a store, a cooperage, a poorhouse, a jail, and a private home. And you think you have too little space!!
In 1872, we learn that the jail was located in the home of Mrs. Patterson, who lived with her son, Charles and his wife Sabra. I do not know why it was moved there; perhaps the Browns sold their home and the new owners did not wish to continue in that line of "work". The Pattersons home was the one that was purchased and razed in 1890 to make room for the Town Hall, so the next jail was housed in the basement of the Town Hall. It could be entered from a back entrance and stairway that led to an area under the stage of the original building. That stage and all remnants were removed when the Town Hall was remodeled in 1987.
Often the only people who were incarcerated in that place were inebriants who were not able to manipulate their way home. Such people were escorted to jail by the constable. In 1847 that person was Ira Buck; in 1850 the position was held by Caleb Nye.
During the memory of Isabella Hicks Hart, the former historian, Mr. John Dill served that position. Mr. Dill had a daughter, with whom Isabella was a close friend. According to her memoirs, she and her friend would occasionally be commissioned to carry a basket, covered by a white napkin, which contained the "prisoner's" dinner. Timidly, those two little girls would walk together from Mrs. Dill's kitchen, carefully transporting this steaming repast to the "bad man" in the jail. Isabella told of being afraid to say a word while they waited for him to finish the meal so that they might take the dishes, napkin, and utensils home to be scoured!
I have no record of when the jail was removed from the town. Perhaps I will locate that tidbit of information as I read further on the subject. Perhaps it was moved when the Monroe County Sheriff's Department was established .I know that the jail had to have been here until at least 1908 or 1910 because Isabella was born in 1900. Perhaps I will discover that information with more research.