The terms "federal penitentiary" and "family friendly neighbourhood" aren't usually used in conjunction with one another.

But this is exactly what happened in Dorchester when a 19th century prison brought with it several houses meant for the guards and their family.

One man who has a special connection with the homes is historical educator James Upham, a regular contributor to Information Morning Moncton's roadside history series.

"Two of my grandparents grew up in this row and two of my great-grandfathers were guards in the pen," said Upham.

'Noble stone structure'

According to Correctional Services Canada, Dorchester Penitentiary was opened in 1880 on land that was bought from Edward Barron Chandler, a former lieutenant-governor and one of the Fathers of Confederation.

"When the property was first acquired on June 8, 1865 for the sum of £60 it included 600 acres, much of the same being marshland," said a CSC report from 1982.

It is the second-longest serving jail in Canada.

Dorchester Penitentiary as it looked in 1899. (Provincial Archives of New Brunswick/Smith Studios fonds (P12\136))

The prison was once a maximum-security facility, but now houses medium- and minimum-security inmates.

At the time it was built, it was seen as a formidable structure for the largely agricultural region.

"The penitentiary is a noble stone structure, substantially built, costing some $140,000, and nearly ready for the accommodation of 120 prisoners," wrote the Christian Visitor on Jan. 28, 1880.

"The cells are roomy and whilst there is the grimness and terror of broken law about the establishment, yet it is as cheerful as a prison can well be made."

Constructing Guard Row

Of course, it's not just enough to have a facility to place inmates, you need guards and other support staff to operate the prison.

And while it's called the Dorchester Penitentiary, it's a bit of a hike from Dorchester proper.

So to house the guards, prisoners were made to build several homes for the guards and their families.

     A modern view of Guard Row. (Village of Dorchester)

According to D.P. Duffy, who wrote a history of the prison for CSC in 1961, inmates built 30 wooden tenements for guards between 1883 and 1900. 

But these wooden structures were all demolished by 1969.

Nine double and single brick tenements were built between 1920 and 1930 and four brick houses were built in the 1950s. These are the structures that remain.

"This area is commonly referred to as Guard Row," said Duffy.

Unique neighbourhood

This made for a picturesque, but unconventional neighborhood.

"My mom's ironing board was made at the Dorchester penitentiary and the kitchen table that we used when I was a kid was made here as well," said Upham. 

"There was a farm … this is where they also got their milk and their bread. Their ice came from the prison reservoir." 

'Two of my grandparents grew up in this row and two of my great-grandfathers were guards in the pen,' said Upham. (Vanessa Blanch/CBC)

In many ways, existence for the guard families was a contradiction.

They lived in beautiful homes, in a picturesque valley — all the while living next door to convicted murderers, rapists and thieves.

"They had a fairly comfortable living in many respects," said Upham. 

"On the other hand, they're also living right down the hill from a massive federal institution."

Of course, having a prison nearby means escapes can, and do happen. The latest one was just last year when convicted murderer Robert Hilroy Legge "walked away" from the prison, only to be apprehended shortly afterward.

 One of the guard homes built in the 1930s. (Village of Dorchester)

The unique living situation led to some interesting routines for the kids of Guard Row.

"Kids playing in their backyards would see somebody's dad come along with a big flashlight," said Upham.

"That person's job was just to make sure everything was OK … Those kids would go to bed knowing that there was going to be another person going through the backyard just to make sure everything was OK twice more that night."