This year (2022) the Orillia Santa Claus parade was held on November 19th. In the last few years, the parade wasn't a "go" ... it was cancelled, so this year's event was much looked-forward to for the community, and surrounding areas.
We didn't make it out this year, but we always did attend in past years. In a way, it was the start of the Christmas season for us. In fact, we lived on the parade route in past years, right across from the Orillia Soldier's Memorial hospital. We had friends and family that would come to our house to watch the parade. The house was nearly ON the sidewalk, making it a convenient place for them to get a hot chocolate and cookies, or use the "facilities". (That house was demolished by OSMH, along with the that was next door to it, and is now, sadly a parking lot.)Some years, it was cold and snowy, other years mild and sunny. At that time of year, you just never knew what it would be on the date of the parade.
From the time our kids were small, it has grown from a somewhat short parade to one that was a large event - not as big as Toronto's but, big enough to be notable, with some astonishingly well-done floats and walkers, horses and other animals.
Some of the businesses in the area have come up with some fairly ingenious float ideas, like this metal Christmas tree one year, or students and teachers that made an environmentally friendly snowman, using left over snack-pack containers. Locally, most business are not large conglomerates, nor worth millions of dollars. I've always loved the unique ideas found in the local parade.
If you are new to Orillia, or one of the nearby surrounding areas, put on a mark on the calendar for early November and watch for the parade dates to be announced. You can also find out by checking the city's website for proposed dates, and for entry requirements if you want to put your own float in it. (Also note the website lists other holiday happenings.)