Tuesday, November 3, 2026

Local: PART 2: Three Infamous Prisoners of Maine's Historic York Gaol (Jail)

In yesterday's blog, I told you about the historic gaol (jail) in York, Maine that dates back to the 1650s. In today's blog I'll tell you about a THREE infamous prisoners, including one escapee who was never caught! Plus you'll learn the difference between a Pillory and stocks because there was a Pillory outside the gaol! 

WHAT IS A PILLORY AND HOW IS IT DIFFERENT FROM A STOCK? 
WHAT'S A PILLORY?   A pillory is a historic wooden or metal punishment device featuring a frame with holes for a person's head and hands, used to lock offenders in public view for humiliation and abuse, as well as a modern verb meaning to criticize someone harshly in public

(Photo: Rob and Tom standing at the pillory outside of the old gaol).

WHAT ARE THE STOCKS? The stocks are a historical wooden or metal device used for public corporal punishment and humiliation, which lock a person's ankles or feet in place while they are seated.     


(Photo: Sign from the 1700s about the crime of murder. It applied to William Deering, one of the prisoners in the 1700s.)  
PRISONER #1 - William Deering, born Sept 17, 1708 in Kittery, Maine was one of the most horrendous prisoners. According to Werelate.com, William killed his wife Mary with an axe about two months after the birth of their last child, and buried her body, but was caught. Boston Weekly Post Boy in one of its July 1749 issues: 'At the Court of Assize and general Gaol Delivery held at York on the 13th of June past William Deering was tried for the murder of his wife on the 8th of February last, and found guilty, and had Sentence of Death passed on him accordingly. He is to be executed on Thursday the third of August next.'   

(Photo: A poster about what happens to people who commit arson (cited as Afron in the poster). 

However, the execution was delayed in response to a petition filed on behalf of William by his cousin Sir William Pepperell, and in the interim, William Deering escaped from jail. The most plausible version of the story alleges that his escape and probable flight to England was arranged and aided by Sir William. He was never caught.             

(Photo: The stone walled dungeon that Patience Boston was held in)

PRISONER #2 -Patience Boston (also known as Patience Samson)
was a 23-year-old Wampanoag and Nauset Native American woman who became one of the most famous prisoners in colonial Maine history. Born in 1711 on Monomoy Island (Cape Cod, Massachusetts), she was bound into servitude at age three after her mother died. In 1734, while bound to the household of Benjamin Skillins in York, Maine (then part of Massachusetts), she lured Skillins’s 8-year-old grandson, Benjamin Trott, to a well and drowned him. : She was confined in the stone dungeon of the Old York Gaol for about a year while awaiting trial and the convening of the Supreme Court. During her imprisonment, she was pregnant and gave birth to a child. Convicted of murder, Patience Boston was hanged in York, Maine, on July 24, 1735. Her stone cell remains at the historic Old York Gaol museum site today.  

(Other photos: The tour guide speaking in the first floor guard's room. The first and second floor guard's rooms had fireplaces. These rooms were built on after the original stone walled dungeon.) 

PRISONER #3- Nathaniel Cole. 
He was known to have a "flat face" which may have helped with his escape. **Date of incarcerations is unknown, but he was imprisoned three different times! Once for debt, another time for escaping, and then another for lewd behavior. 
HIS ESCAPE WAS CLEVER - Windows in some cells have pointed edging around them. One night he took a bloody steak he received for a meal and spread the blood all over the window. There was a fireplace in his cell (this would have been late 1700s or 1800s) so he hid in the fireplace and climbed up it, then called the guard and screamed his face was torn off (or something). The guard came into the "empty" room, saw the bloody windowsill and Cole slipped out of the fireplace and escaped through the open door. 

HOW THE GAOL BECAME A LANDMARK - In 1820, Maine finally became a state (it used to be part of Massachusetts), and the York Gaol became a local gaol until 1860. In 1899 Joshua and Mary Perkins believed in preserving history and purchased the gaol to make it museum. The museum opened in 1900 and has been one ever since. 
DETAILED HISTORY

• Post-1879: The building ceased operation as a jail and was repurposed for alternative uses, including a schoolhouse, a storage warehouse, and a boarding house, which left the structure increasingly dilapidated. 

• 1899: Local residents and summer visitors—led by Mary Emily Sowles Perkins and her daughter Elizabeth Bishop Perkins—launched an initiative to save the historic, crumbling landmark. 

• July 4, 1900: The building officially opened to the public as a museum displaying colonial relics and curiosities, which laid the groundwork for the modern Old York Historical Society*


(Photo: Old York Gaol at night... very spooky!) 

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I'm a simple guy who enjoys the simple things in life, especially our dogs. I volunteer for dog rescues, enjoy exercising, blogging, politics, helping friends and neighbors, participating in ghost investigations, coffee, weather, superheroes, comic books, mystery novels, traveling, 70s and 80s music, classic country music,writing books on ghosts and spirits, cooking simply and keeping in shape. You'll find tidbits of all of these things on this blog and more. EMAIL me at Rgutro@gmail.com - Rob

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