Middlebury will get a new town clerk in ’23

LONGTIME MIDDLEBURY TOWN Clerk Ann Webster will not seek re-election when her term expires next March. She is announcing her decision now in order to give prospective candidates plenty of time to think about running. Independent photo/John Flowers

MIDDLEBURY — Incumbent local officials taking a pass on another term usually try to let people know a couple months prior to election day. It’s a courtesy to prospective candidates who need to reorganize their lives to take on the task of public service.

Middlebury Town Clerk Ann Webster has decided to give her prospective replacements 10 months warning, noting the rigors of presiding over what is essentially the central nervous system of the shire town’s records and elections.

“I always assumed I’d be running one more term, that I’d retire at 70,” said Webster, now 65. “I think a lot of the decision to do this now is if I just don’t run for another term in March, then a new person coming in doesn’t have to have an election year as their first year, and then they’d be going into a presidential election year after that.”

Webster was appointed town clerk-treasurer not long after the horrific events of Sept. 11, 2001. She replaced exiting Town Clerk John Pomainville, then ran successfully for re-election to the post in March 2002.

The town clerk’s job seemed like a great fit for Webster, who had tons of business management and financial experience to offer.

She’d spent 13 years managing the Middlebury Natural Foods Co-op. She’d worked in the banking industry and had logged several years in Vermont Bicycle Touring’s finance department before being laid off in the wake of the impact 9/11 had had on the tourism industry. Actually, clerical work was in Webster’s blood; several of her relatives had served in the town offices through the years, including an aunt, Betty Fitzpatrick, who’d been administrative assistant to several Middlebury town managers.

Some of Webster’s toughest weeks on the job were her first, when she found reams of orphaned town documents within the old Middlebury municipal building at the intersection of College and South Main streets.

“When I first came, there was a lot of organizing to do,” she said. “The first time I opened up the downstairs vault, there was so much stuff in there — even on the floor — you had to step on things. And to a certain extent, I didn’t know where some things were. So I dug in and starting sorting through things.”

That included plenty of land records and property transfers on what looked like tissue paper.

“I almost threw them away,” she said, “until one day, a researcher came in and asked me for an older property transfer record and I realized, ‘That must be what those (tissue paper documents) were.’”


These days, property transfer documents — as well as pretty much all of the information and archives the town clerk deals with — are part of a permanent, digital record. In the years before the 1970s, municipal officials just staked out vault space and stacked documents that weren’t immediately filed.

It’s safe to say that future town clerks will owe a debt of gratitude to Webster for spearheading the organization and digitization of municipal records.

It wasn’t an easy task. In addition to choosing a company (Cott Systems) to do the heavy lifting, Webster had to determine how records could be accessed.

“A lot of the clerks were hesitant; they are all public records, but there seemed to be a hesitation about whether there was anything in those records that shouldn’t be public,” she recalled.

But she and Cotts figured it out. And if there was one silver lining to the COVID-19 pandemic, it’s that it provided time to complete the Herculean records transition. Cotts scanned paper records dating back to 1955, according to Webster.

Digitization and automation have made things more convenient for researchers and residents. A few strokes of a computer keyboard can get you to a lot of what you need, especially as it relates to all of the land records — liens, property transfers, lease agreements and rights of way.

Oddly enough, not everyone was pleased with remote access — at least not at first. Some local researchers wanted to come into the office and actually handle the books, Webster said. But they transitioned.

“Even when researchers were coming in, they were using the online system, so they were getting used to it,” she said.

The few remaining on-site researchers were finally weened from the municipal building by the COVID-19 pandemic.

“People were kind of forced into using (online research), and found they liked it,” she said.

Meanwhile, changes at the state level allowed people to more easily obtain all birth and death records online from town clerks, rather than in person.

“It’s nice when people call us from St. Albans and we say, ‘You don’t have to come to Middlebury,’” Webster said.


With more municipal business conducted online and by mail — and with a pandemic-era election process that now allows easier voting by mail — Webster is seeing far fewer visitors now than she did 20 years ago. The Vermont Secretary of State mailed ballots to registered voters for the primary and general elections in 2020, and now it’s looking like a permanent offering. The mail-in system also allowed town clerks to update their voter checklists, Webster noted.

A secure drop-off box at the Middlebury municipal building has proven a convenient way for people to remit payments, license renewals or election material at the time of their choosing.

“There’s a lot less foot traffic,” Webster noted.

But that hasn’t meant less work.

“I’m totally in favor of early voting and mailing ballots to everyone… but it’s incredibly labor-intensive,” she said.

Town clerks need to verify the voter’s eligibility, fold the ballot, stuff it into an envelope, create a label and ensure the system reflects the person is voting by mail. Then the clerk receives the filled-out ballot, ensures it’s been submitted by the right person, plugs the ballot into the tabulation system, and makes a record of that vote and the person’s status on the checklist.

And if someone’s ballot is returned defective, the clerk’s office has to follow up with the voter and give them a chance to correct it.

“It’s like you’re doing the whole voting step for them,” she said.

Though she expects more people will use mail-in and absentee voting, Webster pointed out town clerks and their helpers still have to set up polling places, which in some cases can take days.

Webster’s legacy will also include having overseen the 2017 relocation of town records from the old municipal building to the current one at 77 Main St.

While some of her colleagues feel nostalgic for the old digs, Webster was thrilled to move out.

“I found the work environment very toxic,” she recalled of the old town offices, located in the reclaimed remnants of the Middlebury High School that burned many years ago.

“It was almost immediate comfort,” she said of the current space.


Webster hopes the town clerk’s position draws several enthusiastic candidates. She believes those interested should possess a dedication to upholding democracy, the Constitution and election laws; be a “people person”; have great organizational skills and the ability to meet deadlines; experience as a paralegal; and be comfortable setting up new office systems and tweaking them based on evolving state standards and policies.

“I’m hoping someone will be interested who is much younger than me, is very tech-savvy and wants to keep moving things forward — website, Zoom meetings, these changes that are happening now that I find myself more resistant to,” she added.

So what will Webster do when she’s released from her rigorous professional regimen?

She’ll have more time to hike, to volunteer with the Champlain Valley Unitarian Universalist Society, to return to choir singing and to tackle puzzles. She’s an avid “Wordle” player and also enjoys reading.

Webster will look back most fondly on her friendships with election volunteers and co-workers, the regular contact with the public, and finding something different to do on the job each day.

“It’s been the hardest job to figure out how to leave,” she said.

Reporter John Flowers is at [email protected].

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