We have planned an 11-day trip to Quebec just before Thanksgiving, and will need to ride 500 km in seven days, plus riding for sightseeing in Montreal before and after the seven-day self supported part of the trip. So we are trying to build our endurance, but It’s been hard to be motivated to ride all day long in the heat we’ve been having.
Cindy and I decided to do a long ride despite the heat, and we chose Caledon Trailway because it’s cooler even in the sun, than riding on the road, and about 50% shady.
I live 15 km from the trail; Cindy lives 21 km from the trail. We met at the end of my street at 9 am. It was already hot, but still below the afternoon predicted high of 29°C.
Mountainview Road in Caledon, which starts just south of the trail crossing, is being rebuilt and is one lane with alternating directions at the moment.

Davis Feeds Farm holds a sunflower festival for two weeks each summer. It is one of the largest sunflower fields in Ontario. You can see in this picture that the sunflowers are past their peak, and the festival is over for now.


The Caledon Trailway is a rail trail conversion of the former Hamilton and Northwestern/Grand Trunk/CN Railway line that operated from the 1870s until 1960 for passenger rail, with freight traffic ceasing several years later. The tracks were removed in 1986. The town of Caledon purchased the section from Terra Cotta to Palgrave in 1989 and began developing it as a recreational trail. It became the first officially designated portion of the Trans Canada Trail. The full length of the Trailway is part of the Greenbelt Cycling Route, and from Inglewood to Palgrave is part of Trans Canada Trail. Northeast of Palgrave, The Trans Canada Trail continues on the New Tecumseth Trail to Tottenham.

Robert, a blogger I follow, wrote about riding from Barrie to Brampton in two parts here. And I wrote about travelling in the opposite direction, Brampton to Barrie, here.
From Highway 9, another 4.5 km on the New Tecumseth Trail, leads to Tottenham.

The South Simcoe Railway offers excursions “operated by the South Simcoe Railway Heritage Corporation, a nonprofit historical association, dedicated to the preservation and operation of railway equipment from Canada‘s steam era“. We used to take our children on the ride with the Easter bunny.

The rail trail is discontinuous since steam trains are still operated on the section between Tottenham and Beeton, which means if one wants to ride to Barrie, there is a 9 km section which must be done on the road.

Another 28 km on rail trail takes one from Beeton to just south of Barrie, on the west side of Highway 400 at Gateway Casinos Innisfil.
Today, Cindy and I turned around at Tottenham. But first, we stopped at Tim Hortons for iced coffee.

There was a new piece of public art at Mill Street and Queen Street, but I couldn’t find out any information about it.

As we were looking at the sculpture, we saw this vehicle drive by.

I would estimate that at least 50% of the trail was in shade and definitely kept us more comfortable than being on the road.

This is in Palgrave. There is a PXO to cross Highway 50 right behind where I was standing to take this picture.

A few hundred metres further on is a very nice rest area open in 1999. The pavilion is based on Palgrave’s Grand Trunk Railway station circa 1900.

The railway crossing sign is from 1960.

All of the curves, just south of the park made for a pretty picture.

There are now signal controlled crossings at The Gore Road, and Old Church Road, which are most appreciated.


We stopped at Four Corners Bakery and Eatery, in Caledon East, at Airport Road, right next to the trail, for gelato. They have a small selection of groceries, bread, pastries, and a hot table. It’s very convenient.



Cardwell Junction is between Mountainview and St. Andrews Roads ( Torbram and Bramalea in Brampton). The concrete abutments that once supported a railroad overpass carrying the Toronto Grey and Bruce Railway (TGB) over the tracks of the Hamilton and Northwestern Railway (HNW), are all that remain of the TGB, built between 1869 and 1872, originating in Toronto, and passing through Bolton, before climbing up the Niagara Escarpment to Caledon Village, and ultimately north to Owen Sound. Around 1890 there were up to eight passenger trains a day through this junction.
These two murals by Blaze Wiradharma were inspired by the history of the area. They were funded by a partnership between the Town of Caledon, which obtained a grant from the Province of Ontario’s Rural Economic Development Fund, and the Caledon Trailway Book Committee.



North of here, a switchback known as the Horseshoe Curve enabled trains to manage the steep gradient of the Niagara Escarpment where the elevation changes by 26 metres in 1.6 kilometres. Cindy and I visited PAMA, the Peel Art Gallery, Museum and Archives, at the end of May and they had a display about railways in Peel. Imagine if we still had this rail connectivity!


The Active Transportation bridge that carries the trail over Highway 10 is being rehabilitated. We turned around before getting to the bridge, knowing that it was closed, but it should be opening soon, with paving beginning next week and taking one to two weeks. It was always very challenging riding the ascent and decent to this bridge, so I’m looking forward to riding over it when the rehabilitation is done. T


Cindy and I did not remember these walls being here on the west side of Kennedy Road in the past, and they appear to be on a new concrete base. I looked on Streetview, and they are indeed newly in this spot. I can’t recall where they used to be, and do not know why they’ve been moved here.

It was much hotter riding back south from the trail into Brampton, but at least it was relatively downhill, with an air conditioned home at the end. I rode 86km; Cindy got a gran fondo (100km). I’ll try for a gran fondo next week.
For those who would enjoy riding the trail, but don’t want to ride to the trail, there is parking for at least a few cars at most road crossings. Larger parking areas are found at: Gore Road north of Old Church Road, Caledon East (Town facilities lots on Old Church Road), Ken Whillans RMA on Highway 10, east side of McLaughlin Road in Inglewood, and on Winston Churchill Blvd near Terra Cotta.
Seasonal portalets are found in Inglewood and Caledon East. Stone benches are placed in many locations along the Trailway.
The Caledon East Community Complex, just east of Airport Road, has indoor washrooms and an outdoor water fountain and water bottle filling station.
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