A few years back, I took a leap and moved my family from our longtime home base in the world-class metropolis of Toronto to a small town a little over an hour to the south and east in Ontario to a town called Ancaster.
Our reasons for moving were several. In the first place, we wanted a change of scenery, somewhere we could enjoy more outdoor space and less concrete and asphalt. At the time, my work situation allowed for such a move to take place pretty seamlessly. And finally, as a family, we had just grown tired of the overcrowded nature and breakneck pace of Canada’s largest city, and we wanted to experience a calmer, more serene way of life.
So, we settled on Ancaster. I remember when we made the decision, we were all impressed by the town’s quiet charm combined with its ample modern-day conveniences. Ancaster was originally a rural settlement (one with a history that dates back to the 1790s), but as time passed, it evolved into something of a bedroom community, as well. It is replete not only with working farms, but also lovely boutiques, quality restaurants, and more than a few highly rated golf courses. It maintains a healthy balance of the pastoral and the suburban, as well as the traditional and contemporary. We knew all this going in—it’s why we chose the place!
But now, after having lived here as official residents for a few years, the town of Ancaster has surprised me and my family in many ways - including two incredible annual events that I’d like to highlight in this post.
The Ancaster Fair
When we first arrived, we were intrigued by the Ancaster Fair, the oldest running fair in Ontario, and decided to check it out. What we found was far more than a traditional country fair with livestock auctions, carnival games, and midway rides—it was a full-on celebration of local culture. We were amazed at the community involvement and pride that went into it! Every year there are craft displays, produce competitions, live local entertainment, homemade food vendors, and demonstrations of skill—everything from quilt-making to how to properly saw through tree trunks. There’s even a demolition derby, a hotly anticipated contest for the whole town! The first time we attended, the atmosphere was incredibly welcoming, it made us truly feel like we were a part of the town and not just transplants from The Six.
Ancaster Heritage Days
Another pleasant surprise was Ancaster Heritage Days, a local summer event that blends the town’s rich history with a great deal of modern-day fun. From the historical re-enactments to the interactive exhibits showcasing Ancaster’s journey from its colonial foundations to today, it’s a great way to learn about the area’s heritage while having a boatload of fun. There are cookouts, concerts, and hayrides transporting people from one section of town to another. But the crowning moment of each annual Heritage Days celebration is the parade down the town’s main thoroughfare of Wilson Street. What is it about marching bands, floats, and boy scouts and girl scouts throwing handfuls of candy at a gathered crowd that makes life just seem so fantastic? But in truth, what struck me most was the sense of community hovering like a benevolent cloud over the proceedings—the volunteers, the local businesses, and the residents all coming together to celebrate the town’s rich past.
All in all, Ancaster has proven to be far more than just a quiet town with good schools and nice parks—it’s a place full of surprises, where the community spirit is strong and the local events are something to get excited about. Speaking on behalf of myself and the rest of the Gleave family, we are so glad we made the choice to put down roots in this lovely community, and we always look forward to attending both the Ancaster Fair and Heritage Days each and every year.
