A Randolph Vibe Feature — 100th Interview (or close to it)
The humble journalist who keeps the record straight
Tim Calabro doesn’t think of himself as important. That’s the first thing you need to know. He laughs off praise, shrugs at compliments, and treats his work as if it’s simply what anyone would do. But it isn’t. Tim holds one of the most essential roles in any community: he is the person who tells our story.
He writes articles, edits the correspondents from all 16 towns The Herald represents, and somehow carries those towns in his head — literally. During our interview, he listed every one of them from memory, in alphabetical order, without hesitation. In that moment, I knew this conversation was going to be something special.
For the Randolph Vibe’s 100th interview, I wanted to celebrate someone who doesn’t just live here — he documents us, week after week, with clarity, humility, mistakes, and a kind of emotional restraint that lets the truth rise on its own. He thinks I’m silly for choosing him. But that humility is part of what makes him so indispensable.
We talked for almost three hours, and I loved hearing insights from the kind, self-effacing local journalist, photographer, husband, and lifelong observer of the world around him.
A life shaped by images, mentors, and turning points
Tim Calabro’s journey into photography began just before his 18th birthday in 2000, when he was a high school senior interning under photographer Bob Eddy. Bob’s mentorship left a lasting mark on Tim, who recalls, “When there wasn’t an assignment, we’d just drive around and look for things… and I got really good at that.” As he told me this, he suddenly stood up, left the room, and returned carrying one of the large black bound volumes of old Herald newspapers — the kind that hold years of community life between their covers. He set it on the table with a soft thud, opened it to a page he wanted to show me, then disappeared again to retrieve another. Each time he returned with a new volume, it felt like he was letting me step a little further into the history he now stewards.
One of Tim’s earliest published photos was a slow-shutter shot capturing the USAF Honor Guard Drill Team at the Air Force Academy in Colorado Springs. The rifles spun in white blurs behind the soldiers, a visual effect Tim achieved with a slow shutter speed. “Those are the rifles spinning,” he said, smiling. “The blur makes the picture.” This image marked the start of a life spent watching closely and capturing moments with care.
At 18, Tim witnessed a moment that would shape his perspective forever. “We heard this whistling outside that sounded exactly like when Wile E. Coyote falls off a cliff,” he said. “We saw the plane fly by our window… and then we heard it hit.” Grabbing his camera, he stepped outside. “Someone told me a second plane just hit the other tower… that was the moment it was clear it wasn’t an accident.” The photo he took that morning is stark and devastating.
After nearly two years at NYU, where he studied Spanish and played baseball while carrying a camera everywhere, Tim reached a turning point. New York was exhilarating but expensive and overwhelming. “I discovered that I can’t afford to stay in New York. College there was really expensive. Honestly, I was a little burnt out on school.”
The Power of Love
More importantly, there was Katie. They had started dating when he was a junior, and she was a senior at South Royalton High School, now White River Valley High School. Having already endured long-distance once, they didn’t want to spend the rest of college apart. “Because Katie had gone to UVM,” he explained, “we were ready to start our life together.”
Tim left NYU, came home for a semester, then transferred to UVM. They spent that year together in Burlington — she finishing her degree, he finishing his coursework. When she graduated, Tim returned to Randolph and began working at The Herald.
Back home, Tim pieced together photography work at The Herald, Bob Eddy’s studio, and the Rutland Herald and Times Argus, often working 60 to 80 hours a week. And through all of it, Katie showed up in the quiet, steady ways that reveal the shape of a life shared. On production mornings, she still gets up at 3:00 a.m. to pick up the papers and deliver them, a detail he mentioned without ceremony, as if it were simply part of the rhythm they’ve built together.
He learned the craft the old-fashioned way: in darkrooms, newsrooms, car rides with Bob, and late-night edits with Dickey Drysdale. He learned how to read a town and how to listen. He also learned the rhythm of community news — the quiet weeks, the chaotic ones, the stories that surprise you, break your heart, or seem small but reveal something essential about the place you live. Slowly, without trying, he became part of the current that carries Randolph forward — the person who notices, documents, and remembers.
By the time he returned to Randolph for good, Tim had grown into someone who knew the paper from the inside out — first as a photographer, then as a writer, then as the person who understood how the whole operation held together. When Dickey Drysdale began meeting with potential buyers, Tim couldn’t picture himself working for any of them. “I couldn’t see myself at the Rutland Herald or the Valley News,” he told me. So he went to lunch with Dickey, talked through what it would mean, and in June of 2015 — at thirty-two — he (and Katie? - confirm) bought The Herald. It wasn’t a dramatic career leap so much as an acknowledgment of something already true: he was the one who understood the paper, the one who cared about it, the one who could carry it forward.
The work that holds us together
After nearly three hours with Tim, what stayed with me wasn’t a single story or quote. It was the way he pays attention — gently, consistently, without inserting himself. It was the way he talks about mistakes as part of the work, not a failure of it. It was the way he sees the connection between a newspaper and the people it serves, how each depends on the other to stay alive. It was the way he speaks about Randolph with a kind of unconditional loyalty that doesn’t need to announce itself.
It made me grateful — for him, for our town, for the stories that hold us together. He understands that the truth of a town is often found in the small, unguarded details. Thanks, Tim!
