Dufferin County & Highlands

Highway 10 north of Brampton changes character quickly. The subdivisions thin out, the land starts to roll, and within 30 minutes you are in Dufferin County, a patch of rural Ontario that feels disproportionately far from the GTA given that its southern edge is barely 70 km from downtown Toronto. Horse farms line the sideroads, the hills get steeper as you approach the Niagara Escarpment, and the towns are small enough that the local coffee shop still functions as the community bulletin board. Dufferin is not a tourist region in the way Muskoka or Prince Edward County are. It is farm country, and that is precisely what gives it its character.

Orangeville

Orangeville, population around 30,000, is the largest town in Dufferin County and its commercial centre. Broadway, the main street, has a walkable stretch of independent shops, restaurants, and the beautifully maintained Town Hall opera house. Theatre Orangeville, a professional company that has operated since 1994, stages a full season of productions and draws audiences from across the region.

The Credit River has its headwaters near Orangeville, and the Island Lake Conservation Area on the town's north side offers trails, fishing, and cross-country skiing. Orangeville is also the southern terminus of the Credit Valley Explorer, a seasonal tourist train that runs north through the hills, though service has been intermittent in recent years, so check schedules before planning around it.

For day-to-day purposes, Orangeville functions as the supply town for the surrounding rural communities. It has a hospital, big-box retail along Highway 10, and enough restaurants that you will not go hungry. Commuters heading to Toronto via Highway 10 and Highway 410 face a 60 to 90 minute drive depending on traffic, which puts Orangeville in a grey zone: close enough to feel like a commuter town, far enough that the commute can wear you down.

Shelburne

Shelburne sits on Highway 10 about 20 km north of Orangeville, a town of roughly 9,000 that has grown steadily as housing prices in the GTA push buyers further out. The main street has a handful of shops and restaurants, and the town's biggest claim to fame is the Canadian Open Old Time Fiddle Championship, held annually in August since 1951. It is the oldest and most prestigious fiddle competition in the country, and it draws competitors and spectators from across North America.

Shelburne is also home to the Dufferin County Museum and Archives, located just south of town on Airport Road. The museum grounds include heritage buildings, a working blacksmith shop, and rotating exhibits on rural Ontario life. For local information and community events, shelburne.com covers what is happening in town.

Hockley Valley

The Hockley Valley, east of Orangeville along the 3rd Line and Hockley Road, is one of the most scenic stretches of the Niagara Escarpment north of the GTA. The terrain is steep enough for a small ski resort, Hockley Valley Resort, which also operates a golf course and spa. The valley is popular with road cyclists, though the hills are serious. The Hockley Valley Provincial Nature Reserve protects a section of old-growth forest along the escarpment edge, and the views from the higher points look south across the Peel Plain on clear days.

Wedding venues have become a significant part of the valley's economy. The combination of rolling hills, mature hardwood forests, and proximity to Toronto makes it an obvious draw for couples who want a rural setting without asking guests to drive four hours.

Mono Cliffs and the Escarpment

Mono Cliffs Provincial Park, located between Orangeville and the Hockley Valley, is one of the best hiking destinations within an hour of Toronto that most Torontonians have never visited. The park has about 30 km of trails winding through cliff-edge forest, open meadows, and along the exposed limestone faces of the Niagara Escarpment. The Bruce Trail passes through the park, and the fall colour here in mid-October rivals anything in Muskoka. Unlike the more popular conservation areas closer to the city, Mono Cliffs rarely feels crowded, even on weekends.

Grand Valley and the Western Edge

Grand Valley, on the Grand River about 15 km west of Orangeville, is a small community of roughly 3,000 that has maintained its quiet agricultural character. The river provides good trout fishing, and the surrounding farmland is some of the best in the county. There is not much in the way of tourist infrastructure, which is part of the appeal. This is a working farm community, not a destination town, and a drive through the sideroads in any season gives you a sense of what rural Ontario looks like when it is not being packaged for visitors.

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