One of my favourite ways to travel is by bicycle. Whether travelling across town or for hundreds of kilometres, it’s a great way to experience the land in which you’re passing through.
I rediscovered cycling in 2007 when I bought a bike to ride alongside my son on some of the trails in the city. Over the next few months I rode more and more and went on longer rides. Eventually I went beyond the city.
In 2010 I rode from Toronto to Montreal with the Friends for Life Bike Rally. This was my first out of town tour and took five and a half days to go about 600 kilometres. From here on I was hooked and I did it again the next summer riding by myself even further to Quebec City for a total of 1,000 kilometres.

In July of 2012, Daegan and I did our first, and longest bicycle trip together: the 500 Kindnesses bike ride. The principle was simple, we created a “Charity Bicycle Ride” that required supporters to spend no money. Instead, through an anonymous web form on our site, supporters would pledge to perform a random act of kindness for someone. Our goal was to achieve a total of 500 before we left for New York City on July 1, 2012.
Because Daegan was still only 13 and we would be going through some cities with busy streets, we thought it best to take a tandem bicycle. It turned out to be an excellent choice for multiple reasons. With us on the same bike we could chat the whole way. If we wanted to listen to music I could put it on my iPhone in the back pocket of my jersey and we could both hear it. Especially nice was that we could each give as much effort as we could. If one of us was feeling tired, we didn’t have to push as hard on the pedals. If we were strong, we could push harder and give the other person a break. And if we needed to move quickly? Well we could both push hard.
You can find the entries from this trip below:
- 500 Kindnesses Ride – Day One
- 500 Kindnesses Ride – Day Two Here Comes the Heat
- 500 Kindnesses Ride Day 3: An Unexpected Stop
- 500 Kindnesses Ride Day 4: Leaving the Lake Behind
- 500 Kindnesses Ride Day 5: Passing Through Cottage Country
- 500 Kindnesses Ride Day 6: Canada’s Capitol
- 500 Kindnesses Ride Day 7: Thank You, Google!
- 500 Kindnesses Ride Day #8: Montreal!
- 500 Kindnesses Ride Day #9: South of the Border
- 500 Kindnesses Ride Day #10: Green Mountains
- 500 Kindnesses Ride Day #11: Crossing Vermont
- 500 Kindnesses Ride Day #12: Home Again
- 500 Kindnesses Ride Day #13 – Route Change!
- 500 Kindnesses Ride Day #14 & 15: Onward to Massachusetts
- 500 Kindnesses Ride Day #16: Todd Learns His Lesson
- 500 Kindnesses Ride Day #17: Back to New York
- 500 Kindnesses Ride Day #18: Rolling Down the Hudson
- 500 Kindnesses Ride Day #19: We made it!
- How to be a Guaranteed Failure
- हमेशा दिमाग की मत सुनो
In 2014 I was really interested in what was happening in Detroit and made a plan to ride there. The plan didn’t work out as expected but was still an interesting experience and I learned a lot. You can read about that one here.
We did a few smaller trips around town in the intervening years but then Daegan and I headed out for another long trip in summer of 2015. This time we headed for Quebec City and turned east from there. You can read about that trip here.
In July of 2017, my son Daegan, and I rode our bicycles to the train station in Toronto, took the train to Montreal and then spent almost a week riding through Quebec, New York, and Vermont. Bicycle touring is one of our favourite ways to travel. Riding creates lots of endorphins that make you feel good, you burn thousands of calories a day and therefore it becomes not just your desire but your duty to eat a lot, and my favourite part is you never know just what’s going to happen or who you’ll meet.
I grew up in Vermont and so this part of the world is among my favourites. The cycling there is especially good with courteous drivers and great scenery. Do be prepared to climb a few hills though!
You can see the entries from that trip here:
- Well and Truly Underway
- Sitting Tight in Plattsburgh
- Riding Day Two – Plattsburgh to Vermont
- Ride Day 3: The Climbing Begins
- Rest day and Day 4
- Abandoned: Winnie’s World
- Ride Day 5 – or was it 5, 6, and 7?
- Summer 2017 Ride by the Numbers
- Ride Day 6: Back to Montreal – and Stormchasing
And of course, that’s not the end. There will continue to be more trips as time goes on…