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Canadian Urbanism Uncovered

Toronto to Montreal, on two wheels: Day 1

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I consider myself a moderately-skilled, but passionate cyclist. When I decided that I wanted to experience traveling from Toronto to Montreal, emissions free, and within three days, it took a mere status update on Facebook before two other friends (JD and Joanne) were on board. We were an eclectic bunch. I was the only one who had recently been on long distance rides, but nothing even remotely close to what we were about to embark on. JD rides a fixed gear Masi recreationally, while Joanne purchased her first road bike a month before our ride. Weeks and days before, we were fairly confident. With hectic schedules and no comprehension of the severity of this ride, we had barely trained. This is a 3 part, day-by-day tale of the challenges of our journey.

Day 1, destination: Picton, Ontario (Duration: 177km)

Despite having slept for only 2 hours (at most), we are up at the crack of dawn. The sun is shining, morale is soaring. Our gear is undesirably heavy but away we go. After getting lost (x3) within the first 45 minutes of riding, we ditched our cycling atlas for the GPS maps on our iPhones. Here, JD and I anxiously await the arrival of Joanne on a bridge near Lovekin, Ontario. We really just wanted to stop and enjoy the view.


Lakeshore Rd., Port Granby: Three chairs, three cyclists… perfect. Morale = still soaring. Comprehension of the distance that we still have to travel = zero. We devour a couple sandwiches I had made. I was starting to think that I may have underestimated the amount of food we needed.

Cobourg: A great town for recreational cycling. We were complimented on our bikes several times as we sat on a patio of a local organic restaurant. We did not come across any dedicated bike lanes downtown, but the traffic was courteous enough that we felt perfectly comfortable riding. It was already 4pm, and we were still about 100km away. With knowledge of the hilly terrain that awaited us, we checked into reality, turned on our iPods and made it a goal to only rest at every 25km mark.

24km later…close enough. Joanne and I discuss our saddle sores in Greek, for the sake of JD.

When JD showed us the loaf’s worth of peanut butter and jam sandwiches he had packed, we laughed… By dinner time the joke was over.

Picton: We arrived at 9pm. Going along a very long stretch of pitch-black country road on our way to Picton made us realize three things: Firstly, my single LED front light is useless without the ambient lighting of a city; Secondly, no noise is the scariest type of noise; And thirdly, that we should never ride at night again. Exhausted, we walked up the final hill after losing the momentum to ride. With no food establishment within a 4km radius, or delivery service available, we ordered a taxi to pick up and deliver sandwiches to our motel. Day 1 was done, and I still could not fall asleep. When I eventually did doze off, I imagine I was probably sleep pedaling.



  1. Looking forward to hearing about the rest of your trip, any chance you would be able to plot it out on a map for us once you’ve made it to Montreal?


  2. This sounds a lot like a trip I did when I was in an international high school in Italy – I tried to bike from Trieste to Rome in a week. The problem was that I hadn’t ridden for a long time, wasn’t used to the bike, used a heavy backpack instead of panniers, and we did far too long distances each day… 

    Granted, you guys have panniers, are more used to riding etc – but I just think you would enjoy yourself a lot more if you spent twice the time getting there! Riding until 9PM in the dark, running out of food etc, is just no fun. 

    But really appreciate the article, would love to do something like this in the summer (much slower though). What was the route – did you follow the Waterfront Trail any?

    (PS: Would be fun with a Spacing article about winter cycling in the age of global warming – looking outside, all arguments about bike lanes being for only half the year should be dispelled, mid-January and it’s packed with bicycles)

  3. I have had hiking and cycling trips much the same: more enthusiasm than experience, or planning. Nothing wrong with that at all! So long as you do not put yourself in danger, you learn more that way than any other. Besides, if nothing goes wrong, and everything goes to plan, there’s no storied to tell.

  4. @Dan C: Will absolutely make a map, great idea.
    @Stian: The night riding was brutal, but we could have avoided it by just starting on time (which we never did….). Also, we were restricted with our time off from work, and wanted a challenge… And yes, the trip was definitely far from planned. I wanted it that way. I think it allows for a much more intimate experience with the landscape. I think you will get a better idea of the route as I post the next two days. We hopped on the waterfront trail from time to time, but did not keep to it religiously for several reasons: it was really romantic and did not support our 3 day schedule; and secondly we just could not find it most of the time and didn’t want to waste time looking. @MR.S: Completely with you.