Just beyond Toronto's back door lie the rolling hills, peaceful rivers, charming hamlets and elevated rural sophistication of Headwaters.

Encompassing Caledon, Dufferin County, Erin, Shelburne and Mono, Headwaters is a mere 45-minute drive from the “Big Smoke” and offers a glimpse into Ontario’s rural reality. While discoveries of nature and community await visitors who eagerly anticipate what’s over the next hill or valley, Headwaters also features international cuisine, upcoming events the world will be watching and a cosmopolitan flair to rival Toronto’s best and brightest.

A Varying Landscape

Showcasing Ontario’s great outdoors, Headwaters is home to thousands of acres of provincial parks, conservation areas, four major river systems and a landscape shaped from nature’s dreams. Visitors flock to this region to hike, cycle, fish and just be one with the earth. Mono Cliffs Provincial Park offers several trails along the Niagara Escarpment, including a six-kilometre section of the Bruce Trail, a canyon on the Spillway Trail and cliffs on the Cliff Top Trail. 

 In Orangeville, the Island Lake Conservation Area features breathtaking views from its lakeside trail, plus fishing and picnic areas. The Terra Cotta Conservation Area in the southwest corner of Erin offers mature forests, rocky outcrops, lakes, pavilions and an amphitheatre. The Belfountain Conservation Area boasts a waterfall, a fountain, a cave and a suspension bridge. In Caledon, the varying landscape of Ken Whillans is for birdwatchers and fishers alike. For otherworldly terrain, the Cheltenham Badlands is a small field of rolling hills covered in Queenston shale—perfect for pictures but not suitable for walking.

World-class Events and More

Known as “horse country,” Headwaters is one of the most concentrated equestrian areas in Ontario. Throughout the region are some of the country’s premier horse breeding farms, coaching and training facilities, riding schools, boarding stables, equestrian ranches and a wide range of equestrian events. In fact, Headwaters will host the equestrian events of the 2015 Pan Am Games, welcoming 150 athletes and 155 horses at the Caledon Equestrian Park.

On Thanksgiving weekend, focus turns to the Erin Fall Fair where animals, cotton candy, quilts and tractors add to the cacophony of laughter and community. For family fun that teaches hard work, Little Creek Ranch schedules day camps for kids, which can also involve entire families planting gardens, picking apples or tending bees.

Duffers should check out the Caledon Country Club, a public 18-hole golf facility featuring a restaurant, patio dining and exquisite banquet facilities overlooking the Credit River, as well as the Shelburne Golf & Country Club, owned by Sam Young who is recognized as one of Canada’s top junior golf coaches year over year.

Should culture be your craving, the Alton Mill Arts Centre in the village of Alton is home to galleries, artist studios, a café, heritage museum and shops such as Gallery Gemma Jewellery, which sells one-of-a-kind pieces in sterling silver, gold and platinum. Orangeville is Headwaters’urban centre, which, in June, hosts the Orangeville Blues and Jazz Festival, featuring free outdoor main stage events and live blues and jazz at local venues. Staging excellent performances, Theatre Orangeville, in its 16th season, has premiered such Canadian works as The Last Resort, War Brides and Little Women. Step back in time at Dufferin County Museum to view its extensive collection of Canadiana, typifying what you’d find in rural Ontario between the 1840s and the 1980s. Visitors who remember a world without cellphones may see bits of their own youthful wardrobe when they view the bell-bottom pants, which fascinate local school kids.

A Taste of Country Living

Headwaters offers diverse dining opportunities from affordable entertainment for kids to gourmet fare in pleasant cafés, cosy pubs and quaint tearooms.

At the Mono Cliffs Inn, a mecca for food and wine lovers in the area, chef Van de Hock is dedicated to the local food movement, creating his menus based on season and availability of local products. In Orangeville, Forage, founded by a husband-and-wife team of French-trained chefs, specializes in seafood, vegetarian and gluten-free options and offers global menu selections. Family is also the focus at Landman Gardens and Bakery at the north end of Grand Valley, where a generational family farm includes a market, a bakery and a stone Blackhouse for hosting communal dinners.

When spirits run high, it’s time for cider at Spirit Tree Cidery in Caledon, which also houses a bakery, kitchen and farm store. Spirit Tree offers taste flights of cider, its unique dry-hopped cider, which tastes more like a shandy than a traditional cider, and to-die-for chocolate goat cheese, locally produced by the award-winning Woolwich Dairy.

For local farm products, Caledon’s Heatherlea Farm Market specializes in meats, delicious frozen prepared meals, baked goods and everyday staples while Downey’s Farm Market promises family fun and food that includes Ontario-grown fruits and vegetables, U-pick and ready-pick strawberries and raspberries, and maple syrup as well as farm festivals, special events and its very own winery. The Headwaters region also hosts two annual culinary events—Taste of Maple (mid-March to the second week of April) and Taste of the Harvest (post-Thanksgiving to Remembrance Day).

Put Your Feet Up

Following a host of outdoor adventures, relax at an award-winning inn, a charming bed and breakfast or get closer to nature at a campground. Nestled in a quaint hamlet, the Millcroft Inn & Spa is the definitive country inn retreat where tranquility, comfort and heritage charm blend in rural serenity and sophisticated hospitality. Or consider the rustic experience at Peace Valley Ranch’s B&B, a family-owned and operated cattle and horse ranch featuring private horseback riding adventures and an opportunity for guests to be involved in real ranch work such as sorting, pasture management, fence checking and cattle drives.

Whether you seek sophistication or youthful soft adventure, the Headwaters Region appeals to a wide range of visitors and connects you with the splendour of rural Ontario.

Travel Planner

To plan your country escape, visit headwaters.ca.