Three Candidates Emerge For Pittsfield's Ward 3

PITTSFIELD, Mass. — Three candidates have announced an intent to run for the Ward 3 council seat: Alisa Costa, Matthew Wrinn and William "Bill" Tyer.

Costa is a local advocate with a career in public policy and community organizing, Wrinn has a background in criminal justice and community involvement, and Tyer has served on various committees and boards in the community. 

Costa announced her candidacy in early March.

"I can't wait to get started doing what I'm most passionate about: creating a conversation between government and people. I think that's when we're at our best. Anyone who knows me since I moved here, I've been one of Pittsfield's biggest fans. And I'm always cheering on local business and individuals from all walks of life," she said in a video announcement.

"I want to use my skills in public policy and community organizing to tackle some of our city's challenges and try to get us to work together toward common goals. I think it's really important to have these conversations. And I can't wait to start knocking on doors and having them with the people of Ward 3 but I want to hear from you too."

Wrinn announced his candidacy on Wednesday.

"This city has always had a small-town feel, sporting events, the parade, Wahconah Park, the Boys and
Girls Club, and community support," he wrote in a press release.

"This community is like no other. There is nowhere else I want to be and there is nowhere else I want to raise my kids. The values of the people of this city are unmatched."

Tyer also announced his intent to run on Wednesday, explaining that he has been a part of the community for a long time and understands what has worked and what has not.

"I have always worked as a volunteer on campaigns state and local for many years," he wrote.

In November, Ward 3 Councilor Kevin Sherman indicated that he will be stepping aside and making room for new leadership in 2024 due to a lack of available time.  

Sherman had thrown his hat in the ring when former Ward 3 Councilor Nick Caccamo did not seek re-election.  He had previously served three terms on the council, during which he was president, before stepping down in 2013.

Wrinn said Sherman's shoes will be difficult to fill.

"Matt has respect, admiration, and regard for what Kevin has done and what Kevin means to this city and its residents," his campaign announcement reads.

He was a K-B Toys representative to the First Night Committee, which was a mayoral appointment by then Mayor Edward Reilly, and was also a founding adult member of the Pittsfield Youth Commission and served as a board member of Girls Inc.

Tyer also served on the Lee Planning Board, as a selectman for that town, and as a representative on the Berkshire Regional Planning Commission.

Now retired, he previously worked for Berkshire Health Systems.

Tyer is raising his children after the death of his wife, Samantha, in 2018. His two daughters attended Herberg Middle School and his son, who has autism, graduated from Pittsfield High School.

In his bid for School Committee, he wanted to look deeply into the special needs programming to see how the district can improve city outcomes and analyze how money is spent to make sure it is in the most productive way.

Costa moved to Pittsfield in 2016 and has been a longtime community volunteer and activist.

She has more than 25 years of public policy and community organizing experience in the fields of public health, anti-hunger, and food systems, and most recently in cross-sector collaboration and systems change while running the Working Cities Pittsfield initiative from 2017-2021.

In 2021, she started a private consulting firm, Engaged Communities, focusing on community engagement and systems change for organizations seeking to build practices that strengthen their diversity, equity, and inclusion efforts.

Nomination papers become available on April 3 and have to be submitted to the register of voters for certification by July 21. The last day to submit nomination papers to the city clerk is Aug. 4, in time for a preliminary election on Sept. 19 and the general election on Nov. 7.

Toys for Tots Bringing Presents to Thousands of Kids This Year

By Breanna SteeleiBerkshires Staff
12:21PM / Friday, December 05, 2025

Volunteers organize toys by age and gender in the House of Corrections storage facility. 

PITTSFIELD, Mass. — Plenty of toys are on their way to children this holiday season thanks to Toys for Tots.

Christopher Keegan has coordinated the local toy drive for the Berkshire Chapter of the Marine Corps Reserve since 2015 and said he has seen the need rise every year, last year helping more than 6,000 kids.

"This is 11 years I've been doing it, and the need has gone up every year. It's gone up every year, and I anticipate it going up even more this year," Keegan said.

On Thursday, the Berkshire County House of Corrections storage facility was overflowing with toys making it the county's very own Santa's workshop. 

Keegan said Berkshire County always shows up with toys or donations. 

"This county is outstanding when it comes to charity. They rally around stuff. They're very giving, they're very generous, and they've been tremendous in this effort, the toys for pride effort, since I've been doing it, our goal is to honor every request, and we've always reached that goal," he said.

Keegan's team is about 20 to 25 volunteers who sort out toys based on age and gender. This week, the crew started collecting from the 230 or so boxes set out around the county on Oct. 1.

"The two age groups that are probably more difficult — there's a newborn to 2s, boys and girls, and 11 to 14, boys and girls. Those are the two challenging ages where we need to focus our attention on a little bit more," he said.

Toys For Tots has about 30 participating schools and agencies that sign up families and individuals who need help putting gifts under the tree. Keegan takes requests right up until the last minute on Christmas.

"We can go out shopping for Christmas. I had sent my daughter out Christmas Eve morning. Hey, we need X amount of toys and stuff, but the requests are still rolling in from individuals, and I don't say no, we'll make it work however we can," he said.

Community members help to raise money or bring in unopened and unused toys. Capeless Elementary student Thomas St. John recently raised $1,000 selling hot chocolate and used the money to buy toys for the drive.

"It's amazing how much it's grown and how broad it is, how many people who were involved," Keegan said.

On Saturday, Live 95.9 personalities Bryan Slater and Marjo Catalano of "Slater and Marjo in the Morning" will host a Toys for Tots challenge at The Hot Dog Ranch and Proprietor's Lodge. Keegan said they have been very supportive of the drive and that they were able to collect more than 3,000 toys for the drive last year.

Volunteer Debbie Melle has been volunteering with Toys for Tots in the county for about five years and said people really showed up to give this year.

"I absolutely love it. It's what we always say. It's organized chaos, but it's rewarding. And what I actually this year, I'm so surprised, because the amount that the community has given us, and you can see that when you see these pictures, that you've taken, this is probably the most toys we've ever gotten," she said. "So I don't know if people just feel like this is a time to give and they're just going above and beyond, but I'm blown away. This year we can barely walk down the aisles for how much, how many toys are here. It's wonderful."