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Winchester Milk Run (79km)

Location: Winchester, United Counties of Stormont, Dundas and Glengarry, Ontario


Route Map:

Distance: 78.7km (48.9 miles)


Suggested Tire Width: 35mm


Amenities: Winchester, the route’s official starting point, includes a convenience store and several restaurants. Slightly off route and just past the halfway point, the hamlet of Williamsburg hosts a gas station and general store. Finally, Chesterville, just 25km from the end of the loop, includes a variety of resupply options.


Estimated Gravel Time: 50%


Parking: Parking can be found at the Joel Steele Community Centre in Winchester, as well the District Arena in Chesterville.


Route Description:


As a general rule, unpaved roads become increasingly difficult to find the closer one gets to Lake Ontario. The region south of Ottawa is no exception. While this loop through Dairy Capital of Canada includes a relatively low percentage of gravel overall, with its mix of plentiful and easy to navigate unmaintained and quiet country pavement, this route has a charm all its own.

Gypsy Lane

Starting from Joel Steele Community Centre in Winchester, exit town St. Lawrence Street, followed by a right onto Gypsy Lane, one of the first stretches of easy to navigate unmaintained that characterize the first half of the loop.

View of Pemberton Rd. heading west

Upon exiting Gypsy Lane via County Road 43, continue south on pavement for a short stretch before returning to unmaintained upon reaching Pemberton Rd. From here, continue south for just over two kilometres to Guy Rd., where the loop follows this quiet stretch of country pavement to the hamlet of Inkerman.

Short stretch of unmaintained prior to County Road 3

After crossing the river, the route remains on quiet asphalt before returning to dirt upon reaching Bailey Rd. Continue south, following a short portion of unmaintained to County Road 3. After another brief section of asphalt, make a left onto Moore Rd., a pretty stretch of gravel that hugs the northern shore Millers Creek to Baldwin Rd.

Moore Rd.

Baldwin Rd. is the route’s next stretch of unmaintained, taking riders past the Oak Valley Pioneer Park to County Road 5. Ideally, the route would make a right here to Devries Rd., but the bridge across the South Branch of the South Nations River is currently washed out (as of May 2021). So the next best option is to make a left and continue briefly on pavement Bongers Rd.

Baldwin Rd

Here, the loop continues south on a series of exposed single lane maintained and unmaintained dirt farm roads to Henderson Rd. At this point, although several short unmaintained dirt options exist along Willow and Sullivan Roads, most of the next 30 kilometres to the town of Chesterville remains on quiet country pavement, where cars are few and far between.

Bongers Rd.
Some of the quiet country pavement that dominates the second half of the route

After leaving Chesterville, head south-west along the northern shore of the South Nation River. Soon, the aptly named River Rd. transitions back to gravel at the intersection of Ball Rd. to the Nation Valley Rd bridge. After returning briefly to asphalt, the loop veers north via Rae Rd. Continue on a mix of gravel and quiet pavement to Gypsy Lane, as the route follows this well-maintained dirt trail back to Winchester.

River Rd

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