This summer, I had the good fortune to spend a week for my birthday in my own backyard… or, well, near enough. With travel restrictions limiting where we could go and what we could do, my partner Peter and I decided to explore the sights and experiences in the nearby region of Headwaters. If you are not familiar with it, Headwaters is the Orangeville, Caledon, Shelburne area… and yes, I know I am missing a bunch of other great places, but these are the more widely known ones to the outside world.

This year was my fortieth birthday. The big four-oh. I normally don’t spend a week celebrating a birthday like this. But, hey, it was a big one. Peter’s birthday is two days before mine, so we do like to celebrate a little bit as a general birthday rule. For this landmark occasion, we settled on a week away, just the two of us (No. Kids!) with days upon days to chillax, enjoy… and for me to come to grips with the fact that I’m getting older.

Our destination this year was Hockley Valley Resort and Spa in Mono, Ontario. I had the double good fortune to be able to write about my adventures for the York Durham Headwaters blog, which you can read about here if you’re so inclined:

A Day of Golf at Hockley Valley Resort
A Spa-Cation at Hockley Valley Resort
Celebrating Wine (and a Birthday) at Adamo Estate Winery
Food and Fire: A Culinary Experience at Hockley Valley Resort

But apart from these particular experiences, there were many more that were just too wonderful not to share. My day on Broadway in Orangeville, for example.

My Day in Orangeville

I have been to the beautiful, historic downtown Orangeville before. I’ve driven the streets and have gazed longingly out at cute shops, antique buildings, lively theatres and fun places to eat. But I’ve never stopped to wander. Now, this is mostly because these previous trips had been business-related… but not entirely.

Because we were staying at Hockley Valley for a week, Peter and I decided to go out and explore downtown Orangeville (he’s brilliant at motivating me to actually get up and get out, since deep down I am a proud hermit). The first thing we did was drive up and down Broadway, which is the main historic street, looking at all of the available dining options. We landed on a cute upscale eatery called Rustik—a wonderfully paradoxical name, I might add.

I’ve written an article before about the legacy of covid on our complement of patio dining (which you can read about here: Spotlighting Our Patio Legacy in York Durham Headwaters). At Rustic, this is what I was talking about. Their outdoor patio was an annexed section of the sidewalk, enclosed by a cute fence and peppered with umbrella-shaded tables. At a time in our history when eateries must adapt to health and safety restrictions, this is what happens when a circumstance is not simply made the best of, but used as an opportunity. The result was a simplified, chic menu set against the backdrop of historic Broadway. It was like having lunch in our own little world.

After Rustik, we wandered. With no aim, no intention. Just wandered. At our whim and leisure, we popped in and out of shops, sometimes making a purchase and sometimes not. We met new people and saw new faces (mask-covered though they were). There was no rhyme or reason to the shops we browsed. There was a glass shop, a comic store, an antique market, a candy shop. All random and incoherent in a beautifully cohesive way that tied in everything Broadway in Orangeville was.

But the best part is that I got to visit places I’ve written about before. I’ve spoken to the owners, was moved by the passion with which they talked about what they do, and now I experienced it first-hand. Living in Durham Region, it’s a bit of a hike to get out to Orangeville, admittedly, and I don’t always have an easy opportunity to visit the places I write about. Fromage is one such business. On our day in Orangeville, Peter and I picked up a delicious selection of deli meat and cheese (for Peter), as well as homemade preserves and artisan crackers (for me) for a few charcuterie lunches back at our room at Hockley Valley. I also snagged a cute Christmas gift for my father. Then there was Maggiolly Art Supplies, a sweet, playful art shop. And though we did not stop in, I enjoyed walking past Theatre Orangeville to at least put a physical location to the place.

Read some of the articles I have written on the above businesses here:

#ShopLocal Spotlight: How Our BIAs are Helping Our Businesses Through Covid-19
Art for the Whole Family
Behind the Scenes (…Literally!) at Theatre Orangeville

It is a bit humbling as a writer to travel to places like these and to experience what I’ve written about in person. I am a strong writer (if I do say so, myself), and enjoy a talent for spinning words into pictures in the minds of readers. In truth, I’m spinning them into pictures for myself at the same time, creating a delightful vision that encourages a visit. To actually go to these places and have my visions confirmed when they are even more magical than I painted them in my head… well, it’s one of my favourite things about being a writer.

My day in Orangeville is one that I will not be forgetting any time soon. It is one I look forward to repeating, and one I suggest you add into your repertoire of memories as well. I hope you enjoy it as much as I did.