Chester Clerk Debbie Aldrich steps aside, but not too far away

By Shawn Cunningham
© 2025 Telegraph Publishing LLC

In 1983, Chester Town Clerk Sandy Walker hired a 20-year-old to be her assistant. And while some in Town Hall may have felt she was too young for the responsibility, Debbie Aldrich seems to have worked out.

Now, with 42 years as Assistant Town Clerk, then Town Clerk and Treasurer behind her, Aldrich has decided to step aside — but not entirely. While she will be leaving the role of Clerk in April, she will continue as Treasurer and help out part time with tasks like accounts payable and payroll.

As Aldrich began to transition to her new role, The Telegraph asked her to tell us about her long tenure in Chester town government and how things have changed.

First, Aldrich explained that in 1983, residents would enter into the Town Clerk’s office through the door on the right side of the porch at Town Hall. A long counter ran from the front to the back of the room, where there was a wall where the counter stands today. On the other side of that wall was a table for the listers who worked with documents from the vault. With fewer records, they could even fit a work table in the vault.

It was a much more paper-intensive job before the office had computers.

“We did the recording of the land records by hand-stamping the documents and filling them in with the date and book and the page and copying the documents onto the long legal paper used in the old books,” recalls Aldrich, “We wrote out all the checks by hand.”

Aldrich remembers that Retha Kendall, who for years was secretary to the town manager and to the chief of police, “used to write out all the water and sewer bills by hand.”

“Even at the time, the number probably ran near to the 600 water users we have today, and those bills were sent out quarterly,” says Aldrich.

Aldrich doesn’t recall exactly when computers were introduced – maybe the early 1990s – but she says they were hard to get used to. A few years later, working a mouse was a new challenge, but the technology helped as the job became more complicated.

“Technology has definitely made the job easier, except when it’s not working,” says Aldrich with a smile, “but the laws have changed so there’s so much more to pay attention to. It’s more complicated, especially with elections. And more people watching you.”

Computers and the internet changed a lot for those needed to use the town’s records.

“We don’t get many people coming in to do genealogy anymore. People do it online,” says Aldrich. “The same with the land records, but there’s now 40 years of those records online so people can just look them up. The last couple of years when real estate was going crazy people were coming in here to do searches.” While land records and their changes are computerized, they are also still recorded on paper, in books just as they were when Aldrich was hired. Aldrich started in Book No. 62. Today’s records are being filed in Book No. 253.

Those needing help in Town Hall have found Aldrich to be efficient, knowledgeable and good-humored, even in the face of the occasionally annoying person that so many of us can be. And dealing with the public can sometimes be stressful.

“There have been a couple of times when I’ve lost my patience and it just makes (a situation) a lot worse,” says Aldrich. “So I’ve always told myself to try and smile and be nice. We’ll get further that way in settling a situation, but there have been times when that hasn’t worked.”

“People are generally pretty good, but it seems they are not as laid back and patient as they used to be.”

Aldrich has worked with four town managers, a host of Select Board members and a slew of Justices of the Peace. In 2005, Walker retired and Aldrich was elected clerk. In 2010, Irene Wood retired and Aldrich was appointed Town Treasurer, a post she was then elected to in 2011.

‘…and we had fun’

Even as late as 1983, emergency calls would come to Town Hall where staff would dispatch Chester police, fire and ambulance. After hours, Retha Kendall and Sandy Walker would dispatch emergency services from their homes. Aldrich recalls that several years after she started with the town, firefighters and the ambulance were dispatched through Springfield, then Hartford. Today, Chester police dispatch goes through the Vermont State Police in Westminster.

Aldrich says that town staff also dispatched the town highway crew, which leads her to recall the camaraderie of that close-knit group. She says that office staff would wish every member of the highway crew happy birthday over the radio. One worker began radioing birthday wishes to Aldrich — even when he moved over to Springfield’s road crew. It’s a tradition he continues to this day by phone, even in his retirement.

“Working with Sandy for 22 years was a lot of fun. She taught me a lot,” says Aldrich laughing. “And we had fun.” Halloween seems to have been especially appealing to the “girls in the office,” as she calls them. They would go out with Ken Barrett, the longtime cemetery sexton, as their driver and play pranks on other town staff.

One year, right before Halloween, then-Police Chief Dick Crowson ordered that no one was going to touch his police cruiser for the holiday. After he left, Aldrich remembers saying, “That sounds like a challenge.” That night, “the girls” snuck along the railroad tracks over to the town garage — laughing so hard that anyone nearby would have heard them — and festooned the inside of the car with decorative cobwebs.

The next day Crowson came in to announce that somebody put cobwebs inside the cruiser. “And we said ‘Really?? I wonder who did that?’ ” Aldrich suspects that Crowson knew and it was their little joke.

Going forward, Aldrich will be working part time – not more than 20 hours a week – and looking forward to spending time with her granddaughter here in Chester, her daughter in Maine and her step-daughter and her two children in New Hampshire. “They play lacrosse, and I’d like to go for the games, which I don’t do now,” she says.