Second Street Second Chances Triples its Outreach Goal

By Sabrina DammsiBerkshires Staff
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PITTSFIELD, Mass. — Since launching a little over a year ago the nonprofit Second Street Second Chances has tripled its original goal.  
 
When the organization first started out its goal was to help 150 people in its first year but as of date it has seen more than 500 people, Executive Director Jason Cuyler said. 
 
Second Street Second Chances works with current and formerly incarcerated individuals to provide the support that they need for a successful reintegration into the community. 
 
It was established when a community coalition started looking into the challenges people go through when being reintegrated into their communities, board President Mark Gold said.
 
From there, the organization put together key partners from health care, cultural centers, legal aid, and other community organizations to aid in providing formerly incarcerated individuals access to resources, Gold said. 
 
"One of the things that we wanted to do here at Second Street is, we wanted to collaborate as much as possible with all the wonderful local community agencies that we have here in Berkshire County, " Cuyler said. 
 
"And we really wanted to dig down deep and find out how we can successfully help people transition back into the community.” 
 
The organization starts working with the individuals while they are incarcerated to determine what resources they need for a successful reentry and will continue working with them when they are released, Gold said.  
 
The non-profit aims to provide formerly incarcerated individuals with job readiness skills and access to job opportunities while treating them with respect and encouragement with the goal to make them productive and contributing members of their communities.
 
On this journey the nonprofit also works towards educating the community so they can embrace these individuals when they are reintegrated. 
 
Recent community educational programming includes the "Insight Out” exhibit at the Berkshire Museum, and the play "Release” at Berkshire Community College
 
It collaborates with Berkshire County organizations to provide or provide access to resources such as medical, mental health, and substance use disorder services, financial and literacy resources, transportation, employment, legal services, and many more. 
 
The establishment of the organization was also spearheaded by Berkshire Community College in partnership with the Berkshire County House of Correction, and the Berkshire County Sheriff's Office.  
 
Over the last 12 years the city has been trying to establish a program like this but despite getting legislators to advocate for it, the initiative did not pan out, Sheriff Thomas Bowler said. 
 
When Gold approached the sheriff's office showing that he already had a vision and understood what was going on in the community it was clear that the best path would be through the non-profit route, he said. 
 
When a person is incarcerated they are entered into a structured environment that they do not have upon reentering into the community. 
 
"A lot of these individuals lack structure, guidance, direction, resources, access to resources, and they miss out on a large number of opportunities,” Bowler said. 
 
It is vital that the community continues to provide those services and access to resources so they can overcome obstacles such as mental health issues, substance use disorders, or lack of education and job opportunities, he said.
 
According to its website, since launching it has received grants from the state and city amounting to $1,015,300. It also receives support from a variety of community members and organizations. 
 
More information on the nonprofit here
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Pittsfield Health Officials to Present Outreach Program

By Brittany PolitoiBerkshires Staff

PITTSFIELD, Mass. — Wheels are moving on local health officials' plan to implement an outreach program that connects unhoused individuals with resources. 

The controversial camping ordinance was sent to the Board of Health in September 2025, and they have determined it is not the best approach for Pittsfield. It was officially scrapped by the City Council last month. 

After months of consideration and a visit to the Northampton Division of Community Care, the BOH recommends piloting an alternative community response program with two new homeless service coordinators who would begin work in the spring.  

On Wednesday, Cambi presented the board with a draft plan. It aims to strengthen the city's public health response to substance use and related community challenges by implementing a peer outreach program that provides harm reduction support services, navigation, and relationship building with vulnerable residents.  

This includes improving coordination with community partners and enhancing health and environmental conditions in the downtown area. 

The immediate priorities, Cambi said, are to rebuild trust and engagement, promote community understanding, and reduce stigma. 

"The context behind this is that there was a policy put in place that was set as a solution. We heard from community members and service providers about how this wasn't the right approach, and now there's been a shift," he said. 

"The city, including the Health Department, needs to own that change and how we need to rebuild those relationships, because we definitely lost the trust of the public." 

He pointed out that the department has already been doing this work with its public health nurse and community health worker, but this program would expand that outreach. A system will need to be put in place for data and program tracking. 

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