Cycling & Trails
Rail Trails & Long Routes
The 38 km Dufferin Rail Trail starts in town and runs to Dundalk. It is the single most under-used asset in the county for anyone on a bike.
Just show up
Free
Four long, flat, mostly-free routes — and the first one starts in Orangeville itself.
Dufferin Rail Trail — 38.1 km
A former rail corridor running Orangeville → Amaranth → Shelburne → Melancthon → Dundalk. Open to ATVs, snowmobiles, hikers, dog walkers, horseback riders and cyclists.
It starts in town, it’s flat because it used to be a railway, and it is the single most under-used asset in Dufferin County for anyone on a bike. Most residents have never ridden more than the first two kilometres of it.
Upper Grand Trailway — 10.5 km
A resurfaced CPR line out of Grand Valley. Four-season. Snowmobiles need a valid permit; other motorized vehicles are prohibited.
Caledon Trailway — 35 km
Flat multi-use rail trail from Terra Cotta to Palgrave, part of the Trans Canada Trail and the Greenbelt Cycling Route. Free, year-round, and just over the county line.
Orangeville’s in-town network — 20+ km
Multi-use trails linking neighbourhoods and parks across town. The Town publishes both a trail map and a cycling map at orangeville.ca.
Details checked July 27, 2026. Fees, hours and closures change — phone ahead for anything that would ruin the trip if it were wrong.
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