Since moving to Canada, my craving for a truly long ride had been left unsatisfied—until now. Back in India, riding with my Southern Riders crew, tackling 500 km+ rides every year was almost a ritual, with some journeys stretching up to 600 km on my trusty FOCUS 29’er MTB. But here, in my new home, that hunger for adventure had yet to be fulfilled—until now.
Armed with a basic BTWIN Riverside 120 hybrid bike and a ton of determination, I set my sights on conquering Yonge Street during a recent long weekend. My prep was minimal, to say the least—basic gear was in short supply, but I couldn’t wait any longer. The original plan was to ride from south to north, but as the prospect of an overnight stay in Barrie loomed, I made a last-minute change: I’d go from north to south instead, fully self-supported.
For those who don’t know, Yonge Street has a bit of history. It once held the Guinness World Record for being the longest street in the world at 1,896 km (1,178 miles), though today, it's "only" about 85 km from Barrie to downtown Toronto. When you throw in some connecting roads, though, the total ride stretches to around 100 km—making it a proper century ride. Yonge Street was originally built by the British in the 18th century as a military road to connect Toronto to the northern Great Lakes, and now it’s a key artery in Toronto’s road system—a symbol of endurance and connection across Ontario.
On the day of the ride, I hopped on the GO train at Union Station, heading for Barrie. By 11:45 a.m., I was standing at the junction of Burton Ave, Garden Dr, and Yonge Street—the northern end of the road. At noon, the adventure began. I started off at a steady pace, cruising at about 20 km/h, and for the first 30 km, everything was smooth.
Then the weather turned on me. What was supposed to be a cool day quickly became a scorcher. I started to feel dehydrated, and my thighs were sending me reminders that they had their limits. Thankfully, I spotted a Tim Hortons and made my first pit stop. (Pro tip: only start a long ride if you know where your next Tims is!)The first stretch of Yonge Street ended at Bradford West Gwillimbury, where I passed some fellow cyclists. A quick nod and a wave later, I was back on the road. My next stop? You guessed it—another Tim Hortons. This one was drive-thru only, so I perched myself on the platform, savouring an IceCapp like it was a gourmet meal.
With renewed energy, I pushed on toward East Gwillimbury, taking a deceivingly named Toll Road (don’t let the name fool you, it’s just a local road). Hunger was starting to set in, so I swung by a Subway for a six-foot sub, fueling up for what I knew would be the toughest part of the ride.
And then... came the hills. Oh man, those hills. The stretch from East Gwillimbury to Richmond Hill was like a cyclist's nightmare—steep climbs, one after the other. My pace slowed to a painful 10 km/h. When I hit Richmond Hill, it was already 5:30 p.m., and I was way behind schedule for my planned GO train ride back to Union Station.
But, just as I was starting to think I wouldn’t make it, the ride smoothed out. What goes up must come down, right? From Richmond Hill onwards, it was mostly downhill. I cruised into downtown Toronto, rolling into the Harbourfront by 8:30 p.m. I was utterly spent but injury-free, and more importantly, satisfied. This century ride had been everything I’d hoped for—a perfect mix of challenge and achievement.The cherry on top? Catching the 9:12 train home and pulled into my driveway by 10:15 p.m., where my wife and kids were waiting with warm hugs. It was the perfect end to an unforgettable day.
Strava Link: https://strava.app.link/K580TU9jDMb
So, what’s next? I’m already planning my next adventure. Got any ideas? I’d love to hear them—drop your suggestions in the comments!
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