City Life treks to one of Ontario’s charming hidden gems for fresh air and local fare

“You’re going to Caledon for a weekend? Why?”

I was asked this question multiple times prior to my two-day adventure in Headwaters, Ont., the area made up by Caledon, Dufferin County, Mono, Shelburne and Erin. You’ve probably heard of (or passed through) this ultra-rural corner of the world just northwest of Toronto, and you might have caught wind that the area’s been labelled as more of an ideal place to retire rather than a perfect road-tripping destination.

Ignore those claims because as it turns out, Headwaters is an unexpected haven of all kinds of fun.

The area recently gained attention for being the host of the Toronto 2015 Pan American Games’ equestrian events this summer, and riding on the wave of this newfound fame, Headwaters has totally rebranded itself. Now identifying as a quick and easy getaway for city dwellers who want to escape the smog without really leaving home, Caledon, Dufferin County, Mono, Shelburne and Erin are opening up their formerly hidden arts and culinary scenes to those passersby who never knew there was really anything to do there. Which, admittedly, was most of us.

Funnily enough, nothing has really changed in Headwaters. It’s still the same pocket of serenity that it’s always been, only now it’s finally decided to tap into its potential as one of Ontario’s jewels. Bubbling with quaint bed-and-breakfasts, a professional theatre company, a plethora of rustic art studios, flying lessons, horseback rides and organic, family-run farms, Headwaters is a place to catch your breath before promptly losing it again — in a good way.

My first adventure on Headwaters soil is a trek out to the Caledon Pan Am Equestrian Park. Revamped specially for the Games, the place is as beautiful as it is impressive. Though I don’t speak equestrian, by the sounds of it this facility is going to blow away the international newcomers with its wide-open spaces, top-of-the-line tech, beautiful architecture and an overall better-quality environment than what most athletes are used to. Toward the tail-end of my tour I’m pleasantly surprised by the unveiling of the Headwaters Parade of Horses, an art installation on-site at the Equestrian Park made up of more than 25 life-size fibreglass horses, each one uniquely painted by a local artist.

The next item on my trip’s agenda is a stop at Plant Paradise Country Gardens, whose name says it all. Nestled in the trees, this place is actually the home of folk musicians Lorraine and Rob Roberts, who in recent years concentrated their passion for plants into a full-on profession. The large property is dotted with gardens bursting with blooms that Lorraine planted herself and can name like they’re her own kids. The Roberts’ story — the one about a city-dwelling couple who escapes the smog by moving north to savour a more rural life — is one shared by tons of other Headwaters folks. Some wealthier downtowners, I find out, even relocate to Headwaters, buy some farmland and rent it out to farmers who can’t afford to buy their own space. The perk: this friendly transaction saves the landowners property tax.

After helping Lorraine pot a day lily (and impressing myself by actually doing it somewhat correctly), I’m off to Heatherlea Farm Market, a family-run farm that seems to have been stolen right out of a western romance novel. A tour of the cattle barn and the on-site market shop shows me how truly “farm-to-plate” the place is. During a cooking lesson in the farm’s commercial kitchen, I’m taught how to prep Angus beef sliders using meat from the farm, and when I settle down with the meal at an outdoor lunch table decked with burlap and lace, Mason jars and fresh flowers, I enjoy it with good stuff like pickles, tomatoes and desserts sourced from other nearby farms.

Local love is a common theme I find throughout my two-day stay in Headwaters, which also ushers me into a jewelry-making class, a candlelit dinner at Hockley Valley Resort and a side-splitting play at Theatre Orangeville. The people who live here love what they do, whether it’s glass-blowing, horseback riding, music-making or goat farming, and there’s a family-like support that exists between neighbours.

My stay in Headwaters is wrapped up with a surprise lunch at another family-run farm, Landman Gardens & Bakery. Nestled in the Landmans’ front yard is a blackhouse – a cosy stone hut designed after the traditional type of house that was popular in Scotland back in the day. We tuck in for a quaint brunch inside the fairytale-worthy hovel, where we’re served three courses of scrumptious homemade everything. I’m happy to hear that the farm hosts lunches and dinners in here on the regular for those foodies who want a “different” celebratory dining experience.

The Headwaters team sends me off with an old-fashioned basket stuffed with local goodies, from a berry pie baked by the mayor of Erin herself (yes, really) to a Mason jar full of manure (yes, really), making me wish I could spend just a bit more time here, in the crisp air and clean scenery at the highest elevation in Ontario. Thankfully, though, I’m leaving not just with a bucketload of rural treats, but also with a long list of ideas on what I’ll do next time I visit — which will definitely be soon.

www.headwaters.ca