I started a love affair with October about 20 years ago, when my husband and I moved to southern Ontario.
I guess I never knew how lovely fall could be, because in northern Ontario, seasons seem to go from summer to winter. It's like in a week, nature looses all signs of summer and you wake up one day with snow. So no, I never had time to develop a love for October, it was one of many winter months. I had never seen so many beautiful colours in my childhood since most years the snow would come before all the leaves had a chance to fall, making them look mostly brown or black. So October quickly became one of my favorite months.
In terms of months of the school year, it's a good month. The children are settled in, routines are established and the days are still warm enough to enjoy outdoor recess.
I love the cool, crisp air... no need to watch for heat warnings or cold fronts, we just enjoy playing outside with little worries about being hydrated and making sure no one has freezing nose tips.
October should be longer! ...or maybe come back around in February when we have been barricaded inside due to the frigid temperatures.