This “Life Stories” profile is part of a collection of articles remembering Vermonters who died in 2025.
Children often did a double take when they saw Roger Wales. With a fluffy white beard and ruddy cheeks, the Weybridge farmer bore such a striking resemblance to Santa Claus that he once graced a Beau Ties of Vermont holiday catalog cover with his grandson on his knee.
If Roger had actually been Santa, he might have swooped through the sky on a MacGyvered, 1970s-era Ford tractor, or maybe driven a team of goats, dairy cows and Brahman cattle pulling a hay wagon full of practical presents.
Physical similarities aside, Roger was not one to dash around chortling hearty “Ho, ho, ho’s!” He cared deeply for family and friends but expressed himself with classic New England reticence. The three surviving sons from his blended family with second wife, Martha Winant, recalled how he responded kindly but with characteristic reserve when they awoke scared in the night as youngsters.
Shawn Wales, now 62, remembered running to his dad after one bad dream: “He didn’t say a word to me but went over to the freezer and got a lime popsicle.” Asa Winant, 53, confirmed that his stepdad always promised lime popsicles would keep nightmares away: “I took it as absolute truth.”
Roger had that kind of understated authority with everyone, no matter their age. Asa recalled how neighbors would drop by and “he’d always help them figure out the solution to whatever they were dealing with: how to get something running again, or how to switch from one crop to another. He never made a big deal about it.”
Roger also set high expectations for everyone, no matter their age. “There wasn’t a lot of screwing around with Roger. He demanded your best attention,” Asa said. When he assigned a chore, echoed Roger’s 27-year-old granddaughter, Addison Wales, “You knew to go and do that just like he told you.”
But Roger didn’t always provide in-depth detail on how to complete a task. Like his father before him, “They kept a lot of stuff close to themselves,” said Roger’s second cousin Harvey Smith, “but if you asked them a question, you’d get a good answer.”
Roger was born to Leonard and Leslie Wales in the family farmhouse on Thanksgiving Day — November 25, 1936. He and his younger brother, Erle, represented the seventh generation of Wales on the farm. In March, at age 88, Roger fell at home and hit his head, likely due to an aneurysm. He later died at University of Vermont Medical Center in Burlington.
Roger’s grandmother and Harvey’s grandfather were siblings. They were two of 11 children, and Harvey recalled the Weybridge farm where Roger grew up “always crawling with family and friends.” In middle school, Roger’s dad arranged for him to stay with a Middlebury family so his son could attend the town school without the twice-daily round trips that were impractical for busy farmers.
Roger shared a bedroom with classmate Bill Mraz during the week, and Mraz came home with Roger on the weekends. The pair cemented a lifelong friendship fishing in Otter Creek, hunting and trekking through the woods, skeet shooting (a sport in which Roger was later state champion), and racing cars up Snake Mountain on the old carriage road. During high school, the two built an alcohol still in a basement science lab. “Just for our own use,” Mraz said matter-of-factly.
Roger was always up for learning new things. When the Middlebury High School ski team coach needed a jumper, Roger volunteered. After graduating from what was then the Vermont School of Agriculture in Randolph, he headed west to attend the Montana School of Mines and then Montana State University, where he was on the ski team. Roger told Martha that he took so many classes at MSU he had to run between them. He also did a stint with the Air National Guard in Texas. For the Vermont farm boy, “It was all an adventure,” Harvey said.
“When other people might despair, Roger would look at the mess and say, ‘This is what we need to do.'”
Roger Waterman
The two worked together for several years starting in the late 1960s when Roger ran the family dairy. Harvey recalled his cousin applying some of what he learned in Montana in an unexpected way: using dynamite to clear tree stumps from his fields. “He was always experimenting, thinking outside the box,” Harvey said.
Roger cut timber from the farm to build one of the area’s first bedded-pack barns, where the cows were free to roam and their bedding and manure composted under them through the winter. He was an early adopter of artificial insemination for breeding, corn silage for feed and labor-saving round bales over the traditional square ones. The farmer used electric polywire to fence cattle in “when nobody thought it would work,” said Addison County farmer Roger Waterman. His dad worked for Roger and named his son after the man who became a mentor and second father to Waterman.
Not every trial brought success. Harvey recalled Roger doing a lot of research before landing on what he thought was a good way to seal fermented feed in his new bunker silo. “It pretty much froze solid,” Harvey said.
But Roger took losses with equanimity. “If he regretted anything, he never showed it,” Waterman said. “He used to say, ‘Woulda, coulda, shoulda, shit.’”
And he never let perfect be the enemy of good enough, Waterman said, recalling Roger’s magician-like ability to conjure mechanical fixes from what others considered junk, often excised from hulking corpses of old machinery.
By the early 1970s, Roger and his first wife, Joyce Hallock, had divorced, leaving him with their three young sons. He sold the dairy herd but continued to farm the family’s 266 acres: haying and tending Brahman cattle for beef, growing buckwheat and potatoes, and raising vegetables to sell at the newly launched Shelburne Farmers Market.
Roger was 39 and Martha 27 in 1976 when she spied him across the room at Middlebury’s Fire & Ice restaurant, where she waited tables. “It was love at first sight for me,” Martha recalled. “He was so intriguing and kind of quiet, had a really strong presence and a twinkle in his eye.”
For their first date, Roger invited Martha and 4-year-old Asa to the farmhouse for dinner of steak, potatoes and peas with his three sons, Steve, Shawn and Scott, then 9, 13 and 15, respectively.
It didn’t take Roger long to ask Martha — whom he quickly dubbed “Tootsie” — to marry him, but she was gun-shy after her failed first marriage. For 19 years Roger quietly persisted, repeating his proposal regularly with “Tootsie, are you ready now?” Martha said.
One day in 1995 when she demurred yet again, Roger calmly said he was done asking. A couple months later, Martha turned the tables and proposed. “He said, ‘Yup,’” she recounted, and walked out the door without so much as a hug. Twenty minutes later, he returned with a marriage license.
After they married, Roger became more involved in Martha’s successful catering business. He called himself “the systems manager” and also served as bartender, grill man and vehicle maintenance guy. Her husband’s logistical help was invaluable if occasionally exasperating, Martha recalled. She’d wrestle for months, for example, with how to feed 200 people in an apple orchard, and Roger would come up with a plan in five minutes.
“It didn’t matter what the situation or problem was,” Waterman said. “He could sort it down to the essential elements and come up with a solution like nobody else I’ve ever met.”
Around 2000, Roger and his sons Shawn and Steve started raising goats and shipping milk to what is now Vermont Creamery in Websterville. Maybe some real Vermonters wouldn’t milk goats, as the saying goes, but the smaller, cleaner animals worked for their family.
“Roger didn’t care what everybody else was doing,” Waterman said. “He was not bound by convention.”
The goat dairy allowed the trio to run a farm business together for about 15 years. Shawn and Steve live independently in the farmhouse where their dad grew up but have navigated learning disabilities for their whole lives. “Roger was thinking of his kids all the time,” Harvey said. “He didn’t talk about that, but I could just see the things he was doing.”
In 2023, Roger’s oldest son, Scott, died unexpectedly from a heart attack at the age of 60. Her husband didn’t talk about that, either, Martha said, but he felt the loss profoundly.
Despite being a man of relatively few words, Roger could connect with anyone and easily made lifelong friends. He once had an extended conversation with Pablo Picasso’s son Claude over the course of a wedding they both attended. On a trip to Montana decades after Roger had left, he and Martha visited members of the family for whom he’d worked when a student.
Among Roger’s close friends was Carlos Cortes, whom he and Martha met on Culebra. The couple took their first trip to the low-key Puerto Rican island in the winter of 1990 and returned annually for almost 30 years. Culebra became a surprise paradise for a man who had previously owned neither bathing suit nor shorts. The first time Roger snorkeled, Martha recalled him marveling, “Oh, my God. You know what’s under there?!’”
During the slow catering and farming seasons, the couple escaped to their warm-weather refuge for up to two months. They hosted friends for Roger’s expertly mixed margaritas, and he spent days deep-sea fishing with Cortes, a local of his sons’ generation.
Cortes said Roger applied himself to learning about sport fishing but never took it too seriously. “He was always telling me, ‘If it was all about catching, we’d go to the supermarket and pick it up. We’re fishing. We don’t have to catch anything,’” Cortes said.
No matter how bad a squall they might land in or how sticky a situation, Roger remained calm, his friend said. Once when they were doing a construction project together, Roger saved Cortes from tumbling off the edge of a cliff by quickly throwing wheel blocks under the front tires of his truck.
“When other people might despair,” Waterman said, “Roger would look at the mess and say, ‘This is what we need to do: boom, boom, boom.’”
After Roger fell in March, Waterman said he felt lucky to be at his hospital bedside during his final hours.
Among the many lessons Waterman said he gleaned from his friend and mentor, probably the most important was to appreciate what you have. “For some people, the glass is half empty and for some, it’s half full,” Waterman said. “For Roger Wales, sometimes the glass wasn’t very big but it was always full.”
This article appears in Dec 24 2025 – Jan 6 2026.
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