During the COVID-19 pandemic, Jimmy Judgey and Gurinder Sandhu started The Driveside which hosts a series of community rides in Scarborough (and later in Hamilton) with a focus on community and inclusivity. Not unlike the GyalDem and ManDem cycling clubs; the latter of which will resume in Summer 2026. Since I never took part in their rides before and I have been curious to check out their Scarborough South Loop route, I checked it off the bucket list at today’s community ride which over 100 people attended.
On the way up, I took the East Don Trail to see how that trail had been progressing. The temporary bridge was removed while it appears some concrete pouring is planned to construct the southern ramp.
While I was able to get up the bridge without the ramp, I do not recommend this for those with cargo bikes until that ramp gets completed.
A look back to the recently constructed northern bridge ramp which is missing a small patch of pavement. Beyond this point, it’s back to the regular programming via Eglinton and Kingston to Guildwood GO station.
After going under the tunnel to get to the southern parking lot, I noticed a sizeable crowd had already gathered for some pre-ride coffee and cookies.
Here’s Jimmy (left), Gurinder (third from left), ride leaders Jen, Jordan, and Ian, and Leah (right) who is also part of The Driveside’s core team.
A pre ride briefing from Jimmy, Gurinder, and Leah. Jimmy thanked Urbane Cyclist, Dismount Bike Shop, and Patagonia Toronto for sponsoring the ride, as well as acknowledged the Gaza Sunbirds which they were raising funds for (including through a raffle). Gurinder gave a land acknowledgement.
The ride started along Westlake and Livingston. Here’s a quick regroup at Livingston and Guildwood Parkway; the only traffic light we encountered during the ride.
Going uphill on the Heathfield Drive path.
A bit of a bike jam to get to the Doris McCarthy Trail. Given the steep rocky downhill and ruts on the right-hand side, only ten riders went down at a time. I DO NOT RECOMMEND doing this trail on a road bike!
Made it to the bottom of the hill at Gates Gully!
A short and muddy ride west leads to a nice spot for viewing the Scarborough Bluffs.
We then took a group photo at Gates Gully which I used for the cover photo.
The trail from Gates Gully to Guild Park was pretty rough where at least a gravel bike is recommended. The TRCA plans to construct a new paved trail from Bluffer’s Park to East Point Park over the next few years with the western section from Bluffer’s Park to Gates Gully being prioritized first.
Going up a steep hill to Guild Park which I had to walk the last little bit after turning off.
Some cheering for the last of the group climbing up the hill.
A brief regroup at the parking lot before continuing to Highland Creek.
A selfie with Ilse and Ian.
Riding east along Guildwood Parkway at Morningside Avenue.
A nice downhill on the Waterfront Trail before Highland Creek.
On the Highland Creek Trail.
One last rest stop at Colonel Danforth Park.
The Highland Creek Trail ended at Greenvale Park which also marked the end of this ride.
Time for some post ride veggie samosas and some alcoholic or non-alcoholic beer.
The final event act was a raffle for some prizes from Urbane Cyclist, Patagonia Toronto, and Dismount Bike Shop. Mohanna (?) pictured here won the Urbane Cyclist prize pack consisting of a t-shirt, water bottle, and bar tape. Nile and Arvin (?) won the two Patagonia prize packs while a prize pack from London, ON based Atwater Atelier was also raffled.
Since Sophie – who won the Dismount Bike Shop prize pack – was also headed back to downtown, we rode together to Kennedy Station. In a good sense of timing, we made it to the subway station just as the rain started.
Thanks to Jimmy, Gurinder, and Leah for organizing today’s ride, to Ian, Jordan, and Jen for their role as ride leaders, and to the over 100 of you who made it out. If you haven’t made out to a ride from this group, I definitely recommend it! Especially their South Scarborough Loop ride provided you have the right bike for the job. 😉
I will do a video compilation at a later date.
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