Diane Calabro
Our Third Person Of Note
Hear ye, hear ye, hear ye!
Announcing Diane Calabro as our magazine's third Person of Note!
Our first Person of Note was Clifford Scofield and was written by a long-time friend of his.
Our second Person of Note was Tony Falcone and was written by Tony and his wife Judi.
Our third Person of Note is Diane Calabro. Her article will be composed a little differently.
Diane is well known in Cheshire and we have decided to ask her fellow citizens and friends
to send "Cheshire Today" vignettes about her decades of service to the community. Please send
your information to infocheshiretoday@gmail.com and we will weave some of your contributions into her article. It will feature our first A to Z list describing our honoree. We need your information to be sent to us on or by March 28th. It can be a sentence or a paragraph.
OPIAO (Only Positivity In And Out)
Ron Gagliardi
Submission for Diane Calabro
Richard Smith
Sun, Apr 12, 6:38 PM
My Time with—and Following the Volunteerism of Diane Calabro
By Richard “Reggie” Smith
If you spend any real time around Cheshire’s history scene, you’ll eventually cross paths with Diane Calabro—or more accurately, try to keep up with her.
My own time working alongside Diane goes back to the early days of Cheshirepedia, when local history was just beginning to find its footing in the digital world. Back then, she wasn’t just participating—she was building. Websites, archives, early video projects… Diane was already thinking ahead, figuring out how to make Cheshire’s past accessible to the next generation long before it became standard practice.
What always stood out to me wasn’t just the volume of her work—it was the heart behind it. Diane has a way of bringing history down to a human level, especially when it comes to kids and families. She doesn’t just document events; she tells the stories of the people who lived them.
Take the WWII letters she painstakingly transcribed—over 200 of them, tucked away in a shoebox. These weren’t just historical documents to her. They were voices. Young men from Cheshire, writing home as they went from high school hallways to the front lines of war. Diane made sure their words—and that fragile moment between youth and adulthood—weren’t lost.
That same focus carries through everything she touches. Whether it’s uncovering the story of the Durand Family’s vaudeville life, helping preserve the memories inside the Norton School Time Capsule, or guiding students through the Hitchcock-Phillips House, Diane keeps the spotlight on everyday life—on what it meant to grow up here, to raise a family here, to belong here.
And she doesn’t just research it—she lives it.
I’ve seen Diane do it all: speaking at events, organizing exhibits, digging through archives, answering community calls for long-forgotten stories, even rolling up her sleeves to physically improve the Historical Society grounds. She’s just as likely to be installing a walkway as she is to be leading a discussion on Revolutionary War history.
Her volunteerism isn’t occasional—it’s constant. Over two decades of it. From her leadership with the Cheshire Historical Society to her role today as Town Historian, she’s been a steady force behind how this town understands itself.
What makes Diane unique, though, is how naturally she connects history to education. As a teacher, that instinct shows. Everything she builds—docent programs, exhibits, talks—has a learning layer baked in. You don’t just walk away informed; you walk away seeing Cheshire a little differently.
And maybe that’s the best way to describe her impact.
Diane Calabro doesn’t just preserve history—she keeps it alive, personal, and connected. For the kids walking through those exhibits today, for the families hearing stories on a local tour, and for people like me who’ve had the chance to work alongside her, she’s helped turn history from something you read into something you feel.
Following Diane’s example, you realize pretty quickly—this kind of volunteerism isn’t about recognition.
It’s about showing up, year after year, and making sure the stories that matter don’t fade away.
Richard Reggie Smith
The A to Z of Diane Calabro's Contributions
A: Award of Merit – Accepted this prestigious Award of Merit from the Connecticut League of History Organizations in 2015 on behalf of the Society.
B: Brick Walkway – Advocated for and oversaw the installation of a new, historic-style brick walkway bordering the back garden of the museum.
C: Cheshire Historical Society – Served the organization for over 20 years, holding roles as President and Vice President before becoming Town Historian.
D: Diane Calabro Meeting Room – The society's dedicated research and meeting space was named in her honor to recognize her lifelong dedication.
E: Enslaved Population Awareness – Helped present and "say the names" of Cheshire’s enslaved population during the annual Children’s March for Peace.
F: Farmington Canal – Researched and promoted the history of the Farmington Canal, sharing stories of passenger travel and local merchant Richard Beach.
G: Guest Speaker – Regularly presents on diverse topics, ranging from local veterans' stories to the town's historic architecture.
H: Hitchcock-Phillips House – Spent countless hours managing this 19-room museum, which she often jokingly refers to as the "second home she never wanted".
I: Inventory Project – Led significant inventory efforts that uncovered hidden treasures like the 1976 Norton School time capsule.
J: Junior Education – Coordinates school tours for third-grade classes, ensuring students from schools like Doolittle learn about their town's heritage.
K: Kitchen & Gadget Room – Curated exhibits in the museum's Kitchen & Gadget Room to show modern children how household items have evolved.
L: Letters from WWII – Transcribed over 200 letters found in an old shoe box, detailing the personal stories of Cheshire kids serving overseas.
M: Memorials & Recognition – Honored by the Cheshire Grange as their Community Citizen and was a key figure in the town's America 250 planning.
N: Norton School Time Capsule – Discovered a 1976 time capsule contained in a milk can during an inventory project at the museum.
O: Open House Events – Organized seasonal events like the Holiday Open House, featuring gingerbread houses and historic decorations.
P: President Emeritus – Led the Historical Society as President until 2022, steering the organization through major modernization projects.
Q: Quickbooks Implementation – Oversaw the transition to Quickbooks for the society's financial reporting to improve transparency.
R: Research Advocacy – Encourages the community to contribute original articles and local history stories to the society's newsletter.
S: Spirits Alive – Managed the popular "Spirits Alive" cemetery tours, which bring local historical figures back to life through performance.
T: Town Historian – Appointed as the official Cheshire Town Historian, responsible for recording and reporting facts about significant local events.
U: Underground Railroad – Researched local homes, like the 1740 cape on Cook Hill Rd, rumored to be part of the Underground Railroad network.
V: Vaudeville Research – Uncovered Cheshire’s ties to Vaudeville, including the local history of the musical Durand family.
W: WWII Transcriptions – Personally transcribed coming-of-age stories from soldiers' letters found during the demolition of the old Plaza Block.
X: eXhibits – Curates and updates exhibits at both the Hitchcock-Phillips House and Town Hall to keep history accessible.
Y: Youth Engagement – Fosters a love of history in local youth through events like the Children's March for Peace and interactive museum tours.
Z: Zeal for Preservation – Continues her work with an ongoing vision to make the house museum a "world-class" destination.