Barrie to Brampton - Part 2 (Caledon Trailway)

Happy Canada Day, everybody!

Part one of my Barrie to Brampton ride covered Barrie to Tottenham including the Thornton Cookstown Trail. While there were some gaps such as from Beeton to Tottenham, it makes for a promising route. Let’s start Part 2 which covers the Caledon Trailway with this picture of the trail entrance.

Next to this entrance, you will find a bike repair stand and a bench with a nice lake view.

However, the trail is not called the Caledon Trailway until you reach Highway 9. The official name for the Mill Street (4th Line) to Highway 9 stretch is the New Tecumseth Trail.

The Caledon Trailway is one of the few trails which I could say “holy shit” for how good it is! The Trailway has these wayfinding signs at regular intervals, while the trail quality is excellent with decent shade.

Palgrave has a nice wooden canopy with lights over the trail and it’s part of the Greenbelt Route.

They even have a covered picnic table, along with plenty of benches along the trail.

The stretch from Humber Station Road to Old Church Road has since been reopened and they offered excellent trail crossings which need to be the standard for all rail trails! 😊

The Caledon Trailway saw lots of riders out that day. This was near Caledon East.

Footrests could be found at Airport Road which are rare for rail trails.

You can even find some good quality murals past Caledon East.

There was a trail closure at Kennedy Road which required a detour along Kennedy Road, Olde Base Line Road, and McLaughlin Road due to work on the Highway 10 pedestrian bridge. 👎

That detour practically ruined what was otherwise a great trail with the road quality on Kennedy Road being very rough and I had to ride slow to avoid damaging the bike. Better off avoiding using road bikes there until construction has been completed which is expected for August 15, 2025. I found out from Jun afterwards that the Highway 10 bridge was opened during last month’s Jack Ride.

Once on Olde Base Line, the paved road (and shoulder) allowed me to get some speed again, though crossing Highway 10 wasn’t that pleasant even with the traffic signal.

Unfortunately, that wasn’t the only trail closure for this ride. Another one appeared at Creditview Road which prompted me to use Creditview – and some side street meandering – to get to Mount Pleasant GO station. Work from Creditview to Terra Cotta (except from Mississauga to Heritage Roads) is expected to be done by October 30, 2025.

Creditview has wide paved shoulders from the Caledon Trailway until you reach Brampton at Mayfield Road.

Once past Mayfield, you can use a multi-use path on the east side until Buick Boulevard where it switches to the west side.

The railway tracks in sight! Turned out I needed to switch sides at Veterans Drive to stay on the multi-use path. Something which underscores why uni-directional cycle tracks are far more practical. Lagerfield Drive also has a multi-use path on the north side leading you all the way to Mount Pleasant GO station! I arrived with about ten minutes to spare to clock in at 100 kilometres!

The train ride back to Union was the first time I saw these newer bike cars with the angled racks. They allow a total of 22 bikes on this train car. Overall, I find accessing the bikes is a lot easier with these newer style racks than the older ones. Just need to get used to lifting the front wheel lever.

Aside from the trail closures, the Caledon Trailway could almost be deemed the gold standard for rail trails with excellent trail quality, plentiful amenities, and safe road crossings. Might need to give this trail a redo soon to enjoy the full experience from Terra Cotta to Tottenham.

The Barrie to Brampton route overall has potential to become a great long-distance one-way ride option which is worth adding to your bucket list. Especially if the Town of New Tecumseth can establish an interim trail from Beeton to Tottenham while the South Simcoe Railway remains an operation, as well as add the promised trail amenities from Cookstown to Beeton. One additional improvement I would suggest is for GO Transit to take their “Trail to GO” signage for the Waterfront Trail and expand it to connect other trails such as the Caledon, Oro-Medonte, and Thornton Cookstown Trails (among others).

As for future rides, I will have to make a note to return to Barrie at least twice to do another part of the Simcoe County Loop Trail towards Penetanguishene and bike to Collingwood when the Stayner to Angus Trail is expected to be completed by Spring 2026.