2026 Scarborough South Loop Ride

Last year was the first time I joined The Driveside for their annual Scarborough South Loop ride which saw some Waterfront gravel riding, a steep downhill at Gates Gully, and the Highland Creek Trail. It was refreshingly different from some of the other group rides I did at the time. Today marked the 5th annual version of their ride which Helen came along as well, so we brought our bikes on the GO train to Guildwood Station.

A good-sized crowd was there by the time we arrived. Some pre-ride coffee was provided, while there was likely at least 100 people as was the case last year.

While the ride was originally supposed to leave at 11 AM, it wasn’t until noon when we started rolling which made me feel sorry for those who arrived at the advertised 10 AM meeting time. And of course for Mozzie who was left at home. Supposedly, there was a delay in getting some snacks over.

Gurinder (centre) and Jimmy (left) welcomed everyone for the ride, thanked some of the ride sponsors, and reviewed the logistics of the ride.

Leah (right) joined The Driveside team about three years ago and handles initiatives such as the Riders Digest and the Community Gear Library, while Robyn (left) was the newest addition who joined this summer. Robyn handles some of the administrative tasks including managing the website.

Finally, we’re on our way!

Jordan with the red Tern bike carried one of two speakers for the ride to give it a party theme.

Along some residential streets such as Sylvan Avenue. One of the passers by on the sidewalk could be seen waving at us.

Given the narrow uphill along the Heathfield Drive path, it took a while for everyone to get up and we waited to regroup.

Arriving at the top of Gates Gully. Those riding were encouraged to keep left and those walking their bikes stayed right.

Descending Gates Gully. At least one person was pulled over because of a flat tire.

Helen made it down!

We then took the path west to enjoy some Waterfront views.

Ben pictured in front of this large pile of sand which wasn’t there last year. I wonder if this is for the Scarborough Waterfront Project given the western segment from Bluffers Park to Gates Gully is expected to start construction next year after the Brimley Road South trail is completed?

We had the usual group photo taken. Thanks Jimmy for sending over the one used for the cover.

The first part of the waterfront riding was covered with large rocks and bricks which meant walking our bikes across.

Aside from that obstacle, the rest of the gravel stretch was pretty smooth. Those who like gravel riding better check this trail out sooner rather than later given it’s only a matter of time that this trail will become paved and/or possibly rerouted.

What goes down must come back up.

A brief regroup at Guild Park.

Entering Copperfield Road after a narrow off-road connect which was single track in spots.

Along the Waterfront Trail before reaching Highland Creek.

A bathroom and water break at Colonel Danforth Park.

Keenan brought the other speaker in a bike trailer which I was surprised he was able to haul it along those gravel segments.

One of the bridges crossing Highland Creek.

Robyn brought out the bubble maker as riders reached their end point at Greenvale Park.

Gathering in Greenvale Park. While there were samosas to be had and a raffle, Helen and I had to catch the GO train to free Mozzie who was cooped indoors all afternoon.

Thanks Jimmy, Gurinder, Leah, and Robyn of The Driveside for putting together this ride. While I sincerely hope future rides are more punctual, it was still a fun ride and nice to see old and new friends. Maybe I will check their Hamilton ride next year if the schedule allows.