Partnership Spotlight: Willowtree Farm
We believe that local businesses are the heartbeat of our communities. Through our Partnership Spotlight series, we’ve been showcasing some of the incredible clients we work with, sharing their stories, values, and the ways they shape life here in Durham Region.
So far, we’ve introduced you to Simply British Foods in Whitby and the Oshawa Clinic Group's new Whitby Health Centre. For our third feature, we’re heading north to Port Perry, California, where the McKay family has built Willowtree Farm into a destination that blends agriculture, retail, and community connection.
Rooted in Family and Farming
Willowtree Farm is, first and foremost, a working family farm. “Number one, we’re a farm and we’re a family,” the McKays share. “We’re picking those strawberries ourselves, we’re raising the beef and the lamb, it all starts here.”
That commitment to farming has been the foundation for everything else. What started as rows of fruits and vegetables has grown into a dynamic operation that includes livestock, on-site retail, and a wide range of seasonal experiences. Customers can visit to pick their own strawberries or pumpkins, shop for fresh produce and meats, or attend one of the many events hosted at the farm throughout the year.
What sets Willowtree apart is the sense of authenticity. The same family that plants, harvests, and raises animals is there to greet customers, share stories, and make visitors feel part of something bigger.
More Than a Market
While farming may be at the heart of Willowtree, the family has worked hard to create a retail experience that connects people to where their food comes from. Their on-site market is stocked not only with fresh produce but also locally raised meats, prepared meals, and specialty items that reflect the farm’s creativity.
The McKays describe it as a balancing act: “There’s the farming side, there’s the marketing side, there’s the retail side. There’s such a huge team that surrounds us to be able to make this all work.” Each area requires expertise, and each family member and staff member brings unique strengths to the table. It’s this diversity of skills, and the willingness to pull together, that keeps Willowtree thriving.
The retail side also plays a key role in sustaining the farm financially. By shortening the gap between farm and table, Willowtree ensures their customers receive the freshest products while also supporting a more sustainable agricultural model.
The Reality of Farm Life
Running a business like Willowtree isn’t a nine-to-five job. In fact, there are days when the work barely stops at all. “If you’re a business owner in retail like we are, you’re on basically 24/7,” the McKays explain.
Their days often begin in the middle of the night, when trucks leave for the Toronto Food Terminal to deliver produce. Later in the day, staff welcome customers to pick-your-own fields, and in the evenings, events might keep the farm bustling until dark. It’s a near-constant cycle of planning, harvesting, marketing, and hosting, requiring the family to remain flexible and ready for anything.
“There’s always a plan for the day,” they say, “but really, you just have to be ready to put out fires. You never quite know what’s going to happen.”
This non-stop pace is both the greatest challenge and the greatest reward of farm life. On one hand, it demands sacrifice and dedication; on the other, it allows Willowtree to create meaningful experiences for their customers and community.
Work-Life Balance, If There Is Such a Thing
Like many entrepreneurs, the McKays joke about what work-life balance really means. “I think we have a good work-life balance. My wife does not think we have a good work-life balance,” they laugh.
The reality is that balance looks different when your business is both your livelihood and your lifestyle. Farming is seasonal, unpredictable, and demanding, but it’s also deeply rewarding. The McKays find joy in seeing families return year after year, children growing up with traditions like strawberry picking or walking through the corn maze. Those moments remind them why they work so hard.
It’s also why community is so important. Knowing that neighbours, staff, and customers are part of this shared experience makes the work meaningful and helps offset the challenges.
Partnership and Peace of Mind
With so much invested in their farm, Willowtree places high value on having trusted partners. For them, farm insurance isn’t just a policy, it’s a relationship.
“Progressive is like family to us,” they explain. “They live in our community. They’re raising their families here just like we are. There’s safety in that. There’s comfort in knowing we’re all in it together and that they’re really here protecting our livelihoods. We couldn’t operate without them.”
Having a dedicated broker like Kristie means they can focus on farming, customers, and innovation without worrying about whether they’re covered. It’s one less stress in an already demanding lifestyle.
This partnership is about more than transactions; it’s about trust. Progressive’s role is to understand Willowtree’s unique risks and ensure they’re protected, so the McKays can do what they do best, grow food and nurture community connections.
Memories That Last Generations
One of the most powerful aspects of Willowtree’s story is its impact on families. The farm isn’t just a place to buy groceries; it’s a place where memories are made. Parents bring their children to pick berries, grandparents visit with grandchildren, and school groups learn about farming firsthand.
“We’ve grown up with these businesses around us and watched them grow,” the family reflects. “We know how essential they are. If they weren’t here anymore, we wouldn’t have those experiences or memories to share with generations to come.”
It’s this sense of legacy that drives Willowtree forward. They’re not just producing food, they’re building traditions that strengthen the fabric of the community.
Looking Ahead
As Willowtree Farm continues to grow, the McKays remain committed to balancing the demands of farming with the joy of community. Innovation, hard work, and teamwork will always be part of the journey. So will the partnerships that help sustain them.
At Progressive, we’re proud to stand beside Willowtree Farm, not just as their insurance broker, but as neighbours, partners, and supporters of their vision. Together, we’re building something bigger than business: a stronger, more connected community.
👉 Learn more about Willowtree Farm and everything they offer at willowtreefarm.ca
👉 Discover how Progressive supports local businesses and farms.