Jason Cuyler is a lifelong resident of Berkshire County and was raised on the westside of Pittsfield. He attended both public and private schools before graduating from St. Joseph Central High School and going on to attend the University of Massachusetts where he earned his bachelor's degree in Sociology, along with a certificate in Criminology.
Following graduation, Jason began his professional career at Hillcrest Educational Center, later working for the Department of Social Services, before joining the Berkshire County Sheriff's Office in 2000 as an entry-level Case Manager. Over the past 25 years, he has worked his way through the organization and currently serves as the Assistant Deputy Superintendent of Community Engagement.
Jason strongly believes in the importance of community and collaboration. He previously served on the Berkshire United Way Board and currently serves on the Christian Center Board of Directors, Hillcrest Educational Centers Board of Directors, Berkshire Community College Board of Trustees, Mill Town Capital Advisory Board, Berkshire Health Systems Community Benefits Advisory Committee, the Berkshire County Sheriff's Charitable Foundation, and the Second Street Second Chances Board of Directors.
Jason is married to Brianna Cuyler and has three daughters, Nyla, Brooklynn, and Emerson.
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If you have not already received your supply of printed tickets, they will be available at our luncheons going forward. You can contact me to arrange a pickup or delivery at anytime. My cell is 814.932.3168 or email to Pittsfieldrotaryauction@gmail.com.
As a reminder, you can instantly get tickets by going to the website - easiest way to get people excited for the event and getting it on their calendar.
Please be pushing hard on getting your expected auction items, searching for new ones, selling program ads and promoting the event.
Jim Bronson provided an update on auction planning and reminded members that, with just three weeks remaining, a significant amount of work takes place after donated items are submitted. This includes Ron Latham manually entering items into the database, developing item packages, coordinating ad entries and logo submissions, and overseeing catalog design and production. A video presentation is also being developed for this year’s auction.
As of February 16, there are 39 items entered into the auction database. To ensure a successful auction, we need more than 400 items. Please continue making your asks and submit donated items as soon as possible.
Saturday March 28th is the big day, Berkshire Hills Country Club, Pittsfield
A volunteer sign-up sheet is being passed at meetings. Be sure to grab your spot
We heard from John McLaughlin, President of the Rotary Club of Pittsfield Foundation (RCPF), who shared an overview of the Foundation’s accounts and current activities. The Foundation’s investments are managed by October Mountain Financial Advisors, with a balance of $722,217.24 as of December 31, 2025.
Members can be proud of the significant impact the RCPF continues to make in our community. The Foundation supports major capital projects, the annual Kagan Award, and scholarships including Nash, Lyon, Paul Harris, and Gene Case. In addition, sustaining funds support ongoing initiatives such as Literacy, Boundless Playground, and Advanced Placement programs.
This year, the Foundation has funded several important projects, including:
Roots Rising Farm Project – $10,000 (Includes naming recognition for Rotary Club of Pittsfield)
South Congregational Church – $3,150 Emergency stove replacement for the community food pantry
Annual Dictionary Project – $6,200 Dictionaries distributed to Pittsfield/Richmond third-grade students
Capeless Elementary School – $6,600 Video and projection equipment
The Rotary Club of Pittsfield Foundation is a 501(c)(3) organization and is grateful for the continued annual support of its members. The wine pairing event remains the Foundation’s primary annual fundraiser, with the possibility of an additional fundraiser currently under consideration.
John also noted that the Foundation actively seeks worthwhile community projects. Members interested in submitting proposals are encouraged to contact him for current guidelines.
Please remember that if you are not going to be present for your assigned board member minute, you will need to reach out to a friendly Rotarian who is willing to take your spot for that day. Amy and Vin have graciously stepped in for those absent in the past.
Jack of Clubs is your ticket to Rotary riches! The pot is currently $185.