January 15, 2024 
Monica Bliss 
The Berkshire Edge 

2nd Street elects Lindsay Maynard as new Executive Director as outgoing director Jason Cuyler joins Berkshire County Sheriff’s Office

Pittsfield— The 2nd Street Board of Directors has elected Sergeant Lindsay Maynard as its new executive director following the departure of Jason Cuyler, who recently announced he has taken a position as Assistant Deputy Superintendent of Community Engagement at the Berkshire County Sheriff’s Office. Maynard will take the reins at 2nd Street on April 1st.

Lindsay Maynard

2nd Street new Executive Director Lindsay Maynard

Maynard, a native of Lanesborough, is currently a corrections officer and corrections caseworker for the Berkshire County Sheriff’s Office. She holds a bachelor’s degree in rehabilitation and disabilities studies with a minor in psychology, along with a master’s degree in clinical mental health counseling from Springfield College. She is also a graduate of the Western Massachusetts County Correctional Officers Academy.

Maynard has been “an integral part of 2nd Street since its inception,” Gold said, noting that the organization works closely with the Berkshire County Sheriff’s Office to place referrals, facilitate aftercare case management, create workshops and other events, and help maintain a seamless transition between incarceration and reentry into the community.

“Gratitude fuels my excitement as I step into the role of Executive Director of 2nd Street. I’m grateful for the trust of Sheriff Tom Bowler and the advocacy of Mark Gold, and I give special thanks to Jason Cuyler for his leadership and guidance,” Maynard said. “I am ready to carry forward the community 2nd Street has created.”

2nd Street outgoing Executive Director Jason Cuyler.
Jason Cuyler said his experience at 2nd Street will help drive him forward at his new position “Working collaboratively with fellow Berkshire County community agencies and the 2nd Street support staff has been an honor, and I eagerly anticipate the opportunity to sustain these partnerships in my new capacity with the Sheriff’s Office,” Cuyler said. “Providing services and support for formerly incarcerated clients has been a rewarding journey, and I look forward to continuing this vital work for the betterment of our community.”

Sheriff Thomas Bowler praised both Cuyler and Maynard for their accomplishments. “I am extremely proud of the incredible work Jason Cuyler has done as executive director of 2nd Street. What started as a simple vision — to work collaboratively with community agencies to address the needs of the formerly incarcerated — resulted in the creation of something very special,” Bowler said.

“Jason proved to be the right fit at the right moment in time. The time has come, however, for Jason to take on an even bigger role within the Sheriff’s Office, “Bowler continued. “I could not think of a better person to assume his role than Sergeant Lindsay Maynard. Lindsay is extremely qualified and is respected by her clients and her peers. I am confident that she will continue what Jason has started with great success. Our community is blessed to have such talented individuals devote their lives to helping others in need.”