114. The South Scarborough Loop

A Love Story About the City I Call Home.

I’ve been working on this post for a long time.

I want to get it right.

You see, the SSL isn’t just a bike ride, or gravel ride, or an adventure; it’s MY ride through MY home town, and it lives and breathes MY past.  And like any truly good ride, it tells a story…

And, you know, it’s a love story, so I want to get the words just right.

The ride–and the story–begin in the middle of Scarborough, at Thomson Park, where a ribbon of awesomeness takes bike paths, trails, dirt, gravel, and roads, through a patchwork of parks, south to Toronto’s Waterfront Trail at East Point Park.  The ribbon then splits in two for either a rip east to Pickering (and then back again), for a westerly sprint along the lake, up a classic Scarborough Bluffs grind, and north a bit right back to the beginning.

It’s a beauty.

“Okay great” you say,  “I’m in..is there a map?”

The story of the SSL includes a lifetime of exploration and adventure, and not only visits a good chunk of my city’s history, but skirts past wildlife that we sometimes forget is there.  If you’re lucky (or if you just know where to look), you might see deer, beaver, barred owls, and spawning salmon.

If you scratch a bit deeper (or if you happen to be riding with me), you’ll pass an unexcavated First Nations village, the lighthouse at Frenchman’s Bay, Fraser Estates, and even the remnants of a post-WWII settlement site that was washed away during Hurricane Hazel in 1954.

I spent my childhood summers playing in the ravines of Highland Creek and Morningside Park, and the hillsides still echo with a soundtrack of innocence and bygone freedom.  That may sound cliche, but if you stop for a moment and listen, I bet you’ll hear it too.

…and if you take a time to look behind that tree, or go down down that trail, or up that hill, you might add to the soundtrack…

“Sweet.  Owls, a lighthouse, and echoes of whatever…what’s the route?”

The route isn’t a ride, it’s a journey.

But it doesn’t just cycle through my life…it rides past a replica of a Greek Theatre skena in a park filled with relics of Old Toronto’s demolished landmarks at the historic Guild Inn, and even rides up an old smuggling route.  Heck, it goes under a train track–three times–and through a tunnel, and on top of a wooden boardwalk!

And if the lighting and water level are just right under South Marine Park, you might even see the wreck of the Alexandria, a Great Lakes steamer ship that sunk a hundred years ago).

“Awesome!  I can’t wait to do it…um, how about a GPS file?”

If you refrain from “all the climbs” (yeah, that’s a route option), and ride at a gentle pace, the South Scarborough Loop can be an easy afternoon outing (with about 350m of climbing).


However, if you nail all of the tough stuff, book it hard, and hammer “all the climbs” you can expect a strenuous grind with about 550m of climbing.


In fact, I’ve been using the loop as one of my principle training rips for almost a decade.

Btw, you can also choose something in between “easy afternoon” and “strenuous”, and that’s the beauty of it, you can literally choose your adventure!

Okay okay, it’s climbey and fun…and sometimes you ride hard.  Can you at least tell us where to start?”

Oh it’s climbey.  Somewhere near the start, after climbing out of the valley twice in quick succession, the SSL wends up and out of the ravine, perched atop an elevated path at UTSC, on the newly-built Valley Land Trail.parks2op_0-1How deep is my connection to the SSL?  The route passes my old elementary school, my old high school, the home where I grew up, and even the hospital where I was born.

In fact, I think it even passes the park where I had my first kiss.  Shhhh.

“Okay great, you kissed a girl once…a trail name…a landmark…anything???”

And it’s always new (the route, not the kisses).  Due to seasonal changes, and daily weather nuance, the scenery and terrain are always different.  Even better than that, I’m basically a kid, and I find new bits all the time, so the route isn’t just a fun pedal through a park, it’s a maze of shortcuts, longcuts, optional climbs–and descents too–crunchy bits, fun stuff, short dips into the forest, or along the water’s edge…just because you can.

While there is an endless list of route options, the main part of the loop remains fairly static:  Thomson Park to Morningside Park, south to the lake, west along the Waterfront Trail, up Gates Gully, and north back the start.  It’s about 35k (with an optional trek east to Pickering and back that adds another 20k).

“Seriously, just say ‘boom’ or something and post the route”

Okay, that’s just it, I don’t really have a route map.  Well, I have a map, but it’s only inside my cavernous head, and every time I try to make a route on my GPS, I find a new trail, or skip a part, or hit one of the many alternates. 

…but this thing ain’t optional.  The route always hits the metal sculpture.  It’s called “Passage”, and it’s at the foot of Gates Gully.  When you approach it from the east, it’s a concrete reminder to take notice–okay, it’s a welded metal reminder to take notice–that your story is about to end violently and abruptly, somewhere up the climb that is Gates Gully:  a 1k, 100m vertical, limestone path.  It is not for the weak willed. 

Also, I once kissed a girl there too!

“Really, another picture, and seriously, enough with the kissing.  Just finish the story, dude!”

Okay, fine.

This map isn’t complete.  Not even close.

But at least it’s a start.

Screen Shot 2020-10-25 at 12.34.16 PM

The image above is pretty much the whole ride, but it’s really tough to capture the little bits, and my GPS doesn’t even pick up some of the stuff, so a bunch of goodly trail is missing.

I’ve been taking solace on the SSL during the Time of COVID, and I ride it a few times a week.  The loop guides me through the current global turmoil by taking a look to the past, and creating a new present.

Once upon a time, there was a South Scarborough Loop…

Now it’s your job to find all of the fun stuff along the way, and tell a new story on the SSL.

The beginning…


6 thoughts on “114. The South Scarborough Loop

  1. Thanks for sharing this. I’ve found pieces of this here and there throughout the pandemic when I’m riding nearly every day (except those days I run), Gates Gully one day, Highland Creek another, but you’ve added a few other pieces I didn’t know about so I’ll be exploring a bit more.

    You really captured some of the magic I feel is on these trails. The Don Trail is more of my backyard and it’s lovely but there’s really something about this route that keeps drawing me to it. Thanks again!


    1. I’m glad you like it. It was tough to capture the story of it and the connection, so it’s nice to hear it landed. I’m working on a post that tries to list some of the little bits that some people miss–like a little rip up to golf course at the bottom of the hill from Greenvale Park, or the new stretch along the top of Grey Abbey Park (that C.R. showed me).

      Liked by 1 person

      1. Those little rips are sometimes the best part. I often plan a route on Komoot before heading out. Early on I would never divert from the route but now if I see a little trail heading off in one direction I often turn on that and figure I’ll either get back to the route or not. Nobody’s grading me on how perfectly I follow the GPX track, after all.


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