When Michael Chamberlain, Windsor County’s sheriff, first took on the job in 1976, deputies had to buy their own uniforms and handguns.
“I actually created the first payroll system,” Chamberlain, 74, recalled. “Back in those days, deputies would work and get paid at the end of the evening.”
After losing a reelection bid in November, Chamberlain’s ready for retirement. The Republican won 36% of the vote, losing to Ryan Palmer, a Democrat and a Ludlow police officer, who received 57%.
Palmer spent more than $25,000 of his own money to sway voters, and pitched himself as a reformist. His campaign motto, “end policing for profit,” referred to the 5% of all department contracts that sheriffs are able to keep. Palmer said he hoped to provide more police services for towns rather than the traffic enforcement common in the Windsor County department.
Chamberlain had seldom faced opposition since he was first elected sheriff. After roughly 50 years working in law enforcement in Windsor County, he’s found silver linings in his defeat.
“It’s gone fast,” Chamberlain said of his time. “I have a grandson, 10 years old. I want to spend some time with him, which I haven’t been able to do.”
In 1971, Chamberlain became a police officer in Woodstock. The town, often chosen as one of America’s prettiest, didn’t look quite the same. Autoshops dotted Route 4 as you entered its borders. The fire station — and police dispatching — happened in the village next to the post office. But for the most part, Chamberlain said, the village’s brick buildings remain untouched.
Chamberlain was first elected sheriff in 1979, and has served for most of the years since, except for a four-year stint in the 1990s when he lived in Louisiana.
During the early years, law enforcement duties were bucolic. Chamberlain reminisced on the evening rounds — ”shaking the handles,” he called it. If a business’s door was unlocked, the cops would call the owner. So long as the shop looked normal, many of the owners didn’t bother coming to lock up.
“There wasn’t an awful lot going on in Woodstock,” Chamberlain recalled.
In 1975, Chamberlain left the Woodstock force to join the Windsor County Sheriff’s Department. In those first years with the department, some of the duties were the same as today: conducting traffic details and transporting people in state custody. But one frequent late-night activity now hardly exists.
“We used to work a lot of the nightclubs throughout Windsor County,” Chamberlain said, remembering three or four spots in Chester and Bridgewater. “There was a lot of alcohol involved, and people would get into a little tussle now and then, but for the most part, we usually had enough officers, you know, we could get it taken care of.”
Reflecting on his service, Chamberlain highlighted his early work with Windsor County’s juvenile court diversion program as one of his proudest achievements. He also pointed to the safety of his deputies over the years and the financial stability of the sheriff’s department today, he said.
Chamberlain will soon hand over the keys to the department to Palmer. So far, the transition has been smooth, Chamberlain said.
“Sometimes the changeover of somebody new, younger, different ideas and things — it’s not a bad thing,” he said. “I’m relieved, in a way. You know, you always hate to lose if you’re running for something, but I was prepared.”
For the first time in more than 20 years, there will be a new sheriff in town.