Today I will send my youngest off to kindergarten for the very first time.

From the sleepless trenches of infancy and the perilous toddler phase (when nearly everything is a choking hazard and sharp furniture corners are avoided at all costs), to the pre-school years where potty-training success and the ability to share are the standards by which parenting skills were judged, the much hailed “First Day of Kindergarten” seemed as far away as the moon, and as elusive as a shooting star.

During trips to the food store, where I must have said “no” dozens of times per aisle, or while on line at the post office, watching my little one careen around the small space like a frenzied puppy, I imagined this day with a pleasure flayed at the edges with guilt. I loved him with a ferocity that all moms share… and yet how could I long for the day when he would be gone from morning until nearly dinnertime?

I remember the morning my oldest left on the school bus for the very first time. I can still feel the damp weight of my daughter’s hand in my own, the slow turning in my belly that was my now-kindergartener, turning flips as I was pulled in two by the warring forces of uncertainty and excitement. As his face searched for mine from behind the window, I could just pick out the faintest glint of resignation. This is what big kids do.  I will do it too, but I’m not sure I’ll like it.

How is that baby-to-be, my littlest kid, a “Big Kid” now?  Where has the time gone?

Two hours after I wave goodbye to him on the bus, I will be hosting a “Boo-Hoo/Woo-Hoo Brunch” at my home.  Technically it is for members of the Wilton Newcomers Club… but truly it is for anyone needing a shoulder to sniffle on, or a fellow mom with whom to rejoice:  I did it!  I raised a kind, empathetic, relatively self-sufficient child capable of being without me for nearly an entire day!

Will I be Boo-Hooing or Woo-Hooing?  Probably a little bit of both, I suspect. But more than anything, I will be cheering for this little person I’ve helped create, with my fingers crossed that he will remember his letters and numbers, and certainly his manners. I’m hoping he will walk into his classroom excited to learn and see not strangers, but instead new friends.

And I’ll be itching for the moment the yellow school bus chugs down our street and I can take his little hand in mine once more.

This is an installment from contributing writer Tara Thompson, president of the Wilton Newcomers Club, providing news and information about WNC events and activities, as well as a look at life in Wilton life from the point of view of a newcomer.