The story of Pineridge Hollow
"I truly believe that when we work in our strengths together, we are way stronger than our individual parts.” - Jan Regehr
jan's story
At the heart of Pineridge Hollow is founder Jan Regehr, whose vision, determination, and passion have shaped the destination it is today.
Jan has always embraced opportunity, seeing not just what something is, but what it could become. By listening closely to her guests and responding to their needs, she transformed a small country gift shop into a thriving gathering place rooted in hospitality, community, and authentic experiences.
Whether creating new spaces, growing fresh ideas, or sharing the things that bring her joy, Jan's passion for connecting people continues to inspire everything we do. Today, she leads Pineridge Hollow alongside her children, Katrina, Zach, and Beth, carrying forward a shared commitment to fostering meaningful connections and creating a vibrant community for generations to come.
Where It All Began: Vernon Road
The First Chapter
Pineridge Hollow began in a charming 1920s log home on Vernon Road, where Jan Regehr opened a country gift shop rooted in community, craftsmanship, and prairie hospitality. As more guests discovered the destination, the Teahouse soon followed, serving homemade lunches, fresh-baked scones, and cinnamon buns.
Gardens Come To Life
With her passion for florals and a beautiful 5 acre property, Jan created themed gardens to share her passion with the guests that visited Pineridge Hollow. Along with the gardens came tours, and many beautiful garden parties, with string quartets, poetry readings, and more.
A New Tradition Begins
The first Fall Fair was held in September of 1995, filled with a farmers market of local makers, food vendors, and games and activities for kids. It was a huge success and a core memory for Jan’s kids and many guests who still visit Pineridge Hollow today.
Building For The Future
To keep up with growing demand, the Carriage House was built as a dedicated space for baking and workshops. Originally intended to include personal-use barn and garage space, it quickly became an important part of Pineridge Hollow's future growth.
Outgrowing Our First Home
With the overwhelming response from guests, it became clear that Pineridge Hollow had outgrown its original location. Thanks to a rare opportunity to temporarily divert nearby hydro lines, the Carriage House was moved to its current home in June 1999. The remarkable relocation paved the way for future expansions and growth of the business.
Where We Continue to Grow: Heatherdale Road
Our New Home Takes Shape
With the carriage house move complete, there was still lots of work to be done. The addition of a front porch, ice cream shop and lots of landscaping was completed in the summer of 1999 in time for the first scheduled wedding!
Bringing Pineridge To The City
As Pineridge Hollow continued to grow, Jan saw an opportunity to connect with guests in the city. When a charming location on Academy Road became available, she opened Pineridge Hollow's second location, bringing the same unique shopping experience to a new community!
Focusing On The Future
When the Academy Road store went up for sale, Jan began looking for a new location in the city. After receiving feedback from her staff, however, she decided to focus her attention on the Heatherdale location instead. Planning quickly began for an expansion of the retail space, creating room for new product categories and allowing the furniture department to grow.
The Fall Fair Returns
After years without a Fall Fair, Jan's daughter, Katrina, was determined to bring it back. With careful planning and the support of a growing team, they reintroduced the beloved tradition on an even bigger scale. Since its return, the Fall Fair has become an annual celebration once again, welcoming more than 16,000 visitors to the property each year.
The Village Becomes Reality
The Village had been part of Jan's vision for many years. After acquiring the land where it now stands, that vision became reality. Built in under a year, The Village is home to nine independently owned local businesses and introduced The Farmers Kitchen, The Studio, The Square, and The Market Building. Learn more about The Village expansion here!
oak knoll farm
At Pineridge Hollow, we've always believed that great food begins with great ingredients. From the very beginning, we've been passionate about serving wholesome, authentic meals that nourish both body and soul. Over the years, we've partnered with local farmers and growers to bring the very best of Manitoba to our guests' tables.
Since purchasing Oak Knoll Farm in 2017, we've been able to bring even more farm-grown ingredients directly to our kitchen. By designing our menus around ingredients grown on the farm and sourced from other local producers, we create seasonal dishes that are fresh, nutrient-dense, and full of flavour.
We believe there's comfort in knowing where your food comes from, and that a thoughtfully grown and prepared meal has the power to bring people together in a truly meaningful way.
the heart of what we do
We strive to lead the way in experience-based dining, shopping, and events.
By sharing the things we love and value with the world, we aim to grow healthy communities, businesses, and people.
Generosity
With our time, other's time, our actions, and our interpretation of others.
Creativity
In the way we work, constantly looking to improve what we do.
Creativity
In the way we work, constantly looking to improve what we do.
Generosity
With our time, other's time, our actions, and our interpretation of others.
Collaboration
With our community and with each other, learning from each person's unique skills and perspective.