A Step Into Oakville’s Past: An Afternoon of History, Connection & Conversation
There is something special about discovering the history that exists quietly in our own backyards.
On a beautiful September afternoon, The Sororum gathered in downtown Oakville for an experience that brought together local history, remarkable stories, meaningful conversation and, as always, the opportunity to connect with an incredible group of women.
Our afternoon began at the historic Oakville Museum at Erchless Estate, overlooking the harbour at the mouth of Sixteen Mile Creek.
It is difficult to imagine a more fitting place to begin exploring Oakville's story.
Erchless was home to six generations of the Chisholm family, beginning with Colonel William Chisholm, who founded the town of Oakville in 1827. Chisholm developed the harbour, and in 1834 Oakville was declared an official Port of Entry into Canada.
But what we discovered that afternoon was that Oakville's story extends far beyond the history of one prominent family.
It is also a story of women who understood the importance of preserving the past, and of Black men and women who came through this harbour in search of something profoundly fundamental: freedom.
The Chisholm Sisters: Women Who Preserved a Legacy
For The Sororum, the story of the Chisholm sisters felt particularly meaningful.
Hazel, Juliet and Isabel Chisholm were the last generation of the family to live at Erchless Estate. Through their stewardship of the home and its contents, an extraordinary amount of their family's history survived.
Furniture, photographs, clothing, documents, personal possessions and the objects of everyday life were preserved rather than simply discarded as one generation gave way to another. And those objects matter.
A historic document may tell us when something happened. But a dress, a handwritten letter, a family photograph or an object used every day can tell us something different: what it felt like to live there.
The sisters became custodians not only of their family's belongings, but of a piece of Oakville's collective memory.
There was something about that idea that resonated deeply with us as a group of women.
History often remembers the people who founded towns, built businesses or occupied positions of public influence. Less visible is the quieter work that so often happens behind those stories—the work of remembering.
Women have long been the keepers of family histories.
They saved the letters.
They kept the photographs.
They remembered the names and relationships.
They passed down the stories.
The Chisholm sisters did this on a scale that ultimately helped preserve an important part of Oakville's history for generations to come.
They were not simply the last Chisholms to inhabit an old house.
They became keepers of its stories.
A Harbour That Represented Freedom
Our exploration of Oakville's past also took us into another profoundly important chapter of the town's history: its connection to the Underground Railroad and the early Black community.
Oakville's location on Lake Ontario made its harbour an important point of arrival for freedom seekers escaping enslavement in the United States during the 19th century.
For some, reaching this shoreline meant arriving in a place where slavery had been abolished.
Imagine what that journey must have represented. The uncertainty, the fear.
The extraordinary courage required to leave behind everything familiar in pursuit of freedom. And then, finally, the sight of land across Lake Ontario.
Standing near Oakville Harbour while learning these stories gave the history an entirely different meaning. It is one thing to read about the Underground Railroad in a book.
It is quite another to stand beside the water and imagine what that shoreline represented to someone arriving after an unimaginable journey. Not simply another port. Freedom.
But what made our exploration particularly meaningful was learning that Oakville's Black history extends far beyond the story of escape.
It is also the story of the people who stayed. The families they raised. The businesses they established. The churches and communities they helped build. And the generations that followed.
The Black Families Who Helped Shape Oakville
The Oakville Museum's Freedom, Opportunity and Family exhibition brings attention to the lives of African-American families who settled in the area during the 19th century.
Among the remarkable stories preserved is that of Branson Johnson, a freeborn African American who arrived in Oakville with his family in 1855.
His Certificate of Freedom, issued by a Maryland court, survived for generations, concealed inside a pocket watch. Such a small object, yet one carrying extraordinary meaning.
It represented something we can so easily take for granted today: the ability to establish and prove one's freedom.
Another important figure was Samuel Adams, who arrived in the Oakville area from Baltimore with his family in 1851.
A skilled blacksmith, Adams established himself in the community and used his resources to help other refugees from slavery build new lives in Canada.
He also contributed to the establishment of the Turner African Methodist Episcopal Church, an important gathering place for Oakville's early Black community.
These families and many others became part of the social and economic fabric of the growing town.
They worked as tradespeople, farmers, craftspeople, barbers and business owners.
They established homes, raised children and contributed to the community around them.
Oakville also became a gathering place for Black Canadians celebrating emancipation and freedom.
Beginning in the mid-19th century, Emancipation Day celebrations brought families and communities together in Oakville's George's Square.
These gatherings were more than celebrations. They were expressions of identity, belonging, resilience and the importance of remembering a shared history.
The tradition continues in Oakville today, connecting the present community to generations who came before.
What became increasingly clear as we learned these stories was that Black history is not a separate chapter of Oakville's past.
It is an essential part of Oakville's history.
And learning about the people behind that history helped us see our own community in an entirely different light.
Walking Through the Stories of the Past
Our historical experience continued as we walked together along Navy Street and toward Oakville Harbour.
The beautiful historic streets and familiar waterfront suddenly took on new meaning.
The harbour was no longer simply a picturesque place to enjoy the view.
It was a place of arrival. Of possibility. Of new beginnings.
The historic homes were no longer simply beautiful reminders of another era.
They represented the lives of people who had worked, struggled, raised families and built communities.
It was a reminder that history does not exist only in museums or behind glass.
Sometimes it happened exactly where we are standing.
And sometimes, all it takes is someone sharing a story for us to see a familiar place in an entirely new way.
From History to a Living Family Story
Our walk eventually led us to Paradiso Oakville, where we gathered around the table for lunch.
And this was where the different threads of our afternoon came together in a particularly meaningful way.
Our guest speaker, acclaimed Canadian actress and singer Arlene Duncan, wasn't simply joining us to share stories from her remarkable career.
Arlene is an Oakville native whose own family history is woven directly into the Black history we had spent the afternoon discovering.
In fact, the stories we had been hearing weren't distant history for Arlene.
They were her family's stories.
Arlene is a fifth-generation Canadian on her father's side, with family roots in Oakville stretching back more than 170 years. Her great-great-grandfather, Samuel Adams, was among the early Black settlers who established lives in the community.
Another ancestor, Benedict Duncan, escaped slavery in Maryland through the Underground Railroad and eventually made his home in Oakville. These weren't simply names in historical records. They were people who built lives here. They raised children here. They worked, worshipped and helped shape a community that their descendants would continue to call home.
And generations later, one of those descendants was sitting around a table with us.
That connection was extraordinary.
A Family Legacy of Community, Culture and Storytelling
Arlene's family history is also a remarkable example of how the work of one generation can influence those that follow.
Her father, Alvin Aberdeen Duncan, was a Second World War veteran who served in the Royal Canadian Air Force and later became an important advocate for preserving Oakville's Black history.
He worked to ensure that the contributions of Oakville's early Black families were recognized and remembered, sharing their stories with students and the broader community.
His commitment to preserving history was particularly meaningful in a town where so much of the early narrative had traditionally focused on its founding families.
Arlene's mother, Icilda Duncan, who was born in Jamaica, also played an important role in building community.
She founded the Canadian Caribbean Association of Halton, creating opportunities to celebrate Caribbean culture, strengthen community ties and foster a sense of belonging.
In different ways, both of Arlene's parents understood the importance of heritage, identity and community.
And their daughter would carry that legacy forward through her own remarkable life.
Raised in Oakville, Arlene attended T.A. Blakelock High School before studying musical theatre at Sheridan College.
Her passion for performing began at an early age, eventually leading to a successful career spanning theatre, television, film and music.
But what made our conversation with Arlene so memorable wasn't simply hearing about her professional accomplishments.
It was hearing the woman behind them.
She shared stories with warmth, humour and openness, offering glimpses into her family, her experiences and the journey that shaped her. As a mother of two sons, Matthew and Yuri, Arlene has also carried forward her family's legacy into another generation.
Once again, we found ourselves reflecting on the connections between parents and children.
The stories we inherit.
The traditions we preserve.
The lessons we learn.
And the memories we pass forward.
In 2026, Arlene participated in the unveiling of a memorial at Burnet Park honouring her ancestors Samuel and Martha Adams and Oakville's early Black community.
More than 170 years after her ancestors arrived in Oakville, their descendant continues to help ensure their stories are remembered.
It was a powerful reminder that history is not something that simply ends.
It continues through the people who carry it forward.
And there was something especially poignant about spending the first part of our afternoon exploring Oakville's history and then sitting down with a woman whose family had lived that history.
The past suddenly didn't feel very far away at all.
As our afternoon unfolded, one idea seemed to connect every part of the day.
Stories survive because someone chooses to tell them—and someone else chooses to listen.
Throughout history, women's lives have not always been recorded with the same care or prominence as those of men.
And yet women have always been there.
Building families and communities.
Creating businesses.
Making art.
Challenging expectations.
Preserving traditions.
Navigating change.
And quietly influencing the world around them.
Sometimes their names appear in history books. Often, they don't. But their stories still matter.
We saw this in the Chisholm sisters, who preserved the physical traces of generations before them.
We saw it in the stories of Oakville's early Black community, including the women who built families, sustained traditions and helped establish new lives in a new country.
And we saw it in Arlene Duncan, who carries the stories of her ancestors while adding her own extraordinary chapter to her family's history.
It made us think about how history is actually created. Not only through grand events or public achievements. But through ordinary lives.
Through family stories. Through photographs tucked into drawers and letters kept in boxes.
Through the stories a grandmother tells her granddaughter. Through conversations around a dinner table. Through one woman saying to another, You should know this.
And perhaps that is why women's stories matter so much.
Because when they disappear, we don't simply lose the story of one woman.
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This Is Why We Gather
In many ways, this afternoon captured exactly why we created The Sororum.
The Sororum began with a simple belief: women need meaningful spaces to gather throughout every stage of their lives.
Spaces where we can be curious.
Where we can continue learning.
Where we can discover remarkable places and meet fascinating people.
Where we can talk about history, culture, art, careers, families, reinvention, challenges, ambitions and all the experiences that make up a woman's life.
But most importantly, spaces where we can hear one another's stories.
Because something wonderful happens when women gather around a table.
Someone tells a story. Another woman recognizes something of herself in it.
Someone asks a question. Someone else shares something she hadn't planned to share.
We laugh. We learn. We discover that our experiences are sometimes remarkably different—and sometimes remarkably similar.
And slowly, connection happens.
Not because we were told to network. Not because we exchanged business cards.
Simply because we had the time and space to know one another a little better.
That is the kind of community we want The Sororum to be.
A place where curiosity brings us together and conversation creates connection.
A place where we can continue discovering the world around us while learning something about ourselves and one another.
And a place where women's voices, experiences and stories are valued.
Our Stories Are Part of History Too
There was something particularly poignant about spending the first part of our afternoon looking backward and the second part sitting around a table together.
Because one day, our lives will be history too.
The careers we built.
The families we raised.
The risks we took.
The things we survived.
The friendships that sustained us.
The times we started again.
The lessons we learned much later than we expected to.
The things we are proud of.
The things we wish we had known sooner.
These stories matter.
And women don't need to be famous, historically significant or extraordinary by someone else's definition for their experiences to be worth sharing.
There is wisdom in an ordinary life.
There is history in a family.
There is value in remembering.
And there is power in being heard.
Perhaps part of what we are creating at The Sororum is simply a place where we make room for that.
A place where women can continue to experience new things, form new friendships and remain curious about the world—and about one another.
A place where we recognize that every woman who walks into the room brings with her decades of experiences, stories, knowledge and perspective.
And that there is still so much we can learn from each other.
Until We Gather Again
We are incredibly grateful to the team at the Oakville Museum at Erchless Estate, and especially to Abi and Lauren, who brought Oakville's history to life with such knowledge, thoughtfulness and enthusiasm.
Thank you to the wonderful team at Paradiso Oakville for welcoming us so warmly and providing the perfect setting for our afternoon together.
And our heartfelt thanks to Arlene Duncan for sharing not only her remarkable career with us, but her family history, her experiences and her wonderful spirit.
Finally, thank you to every woman who joined us. Because ultimately, The Sororum isn't the museum we visit, the speaker we invite or the beautiful table around which we gather.
The Sororum is the women who come.
The women who arrive curious.
The women who ask questions.
The women who share something about themselves.
The women who listen to someone else's story.
The women who welcome the person sitting beside them.
And the women who leave knowing someone they didn't know when they arrived.
Our afternoon in Oakville reminded us that preserving women's stories matters.
But so does creating new ones.
And every time we gather, that is exactly what we are doing.
The Sororum
Inspire. Empower. Belong.
Interested in joining us for a future gathering? Become part of The Sororum community and discover what happens when women come together through curiosity, conversation and connection.
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