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Why Ride?

Wind your way through the beautiful and challenging countryside surrounding Caledon, while raising funds to power a national network of young leaders working to end the stigma that surrounds mental health.

Volunteer-run and sponsor-supported, Jack Ride is’s largest fundraising event of the year. As our generous sponsors cover the cost of the ride, every rider-raised dollar goes directly to providing the tools and resources young leaders need to transform how we think about mental health.


Register on your own or as a team. Ride in memory of a loved one or as a sign of your commitment to ending mental health stigma.

The registration fee for Jack Ride is $110 and includes: entry into the ride, a jersey, an awesome swag bag, breakfast and a BBQ lunch.

Register before Jan. 31st for our $60 Early Bird rate! Register Now Each registered rider is required to raise a minimum of $250 in support of youth leadership in mental health.


Jack Ride is entirely powered by volunteers. Dedicated folks donate their time and support every aspect of the ride from planning, logistics, swag nights, set up and tear down.

Interested in volunteering?
Register to be a Ride volunteer!

Volunteer Sign-Up


Jack 25

Suitable for youth, families and new riders. Hilly terrain, but manageable for new and young riders. Will take approximately 1 to 2.5 hours depending on individual pace.

Jack 50

A reasonable challenge for youth, families, and inexperienced riders. Some hilly terrain. Will take approximately 2-4 hours depending on individual pace.

Jack 100

For experienced riders. Several pace groups. Hilly terrain but a good challenge for experienced riders. Route goes through the Badlands. Will take approximately 4-5.5 hours depending on individual pace.

Big Jack

For serious, very experienced riders. Challenging pace. Hilly terrain. Route goes through the badlands. Will take approximately 4-6 hours.

I'm an avid cyclist, and this is always one of my favourite rides. I rode with someone that I met at last years ride. This ride is the perfect platform to start the conversation about mental health for me with my friends and family.
This ride was more than a sporting event for me. As someone who has struggled with my mental health throughout my life, it made me emotional to see all the support that was being given at the ride. To see that many people who cared about an issue so close to my heart fueled me through every hill and harder patch. It was a great ride and a great experience.
I thought a lot about mental health, more than ever before. A friend's son passed away in November and I was unsure about how to approach it. This was a brilliant way to do something meaningful for him and his family.


Where does Jack Ride take place?

Jack Ride is held at:

Caledon Ski Club,
17431 Mississauga Rd Caledon, ON 

What is the route like, terrain wise? Difficulty?

There are some hills on the route. We have four route options available, and the shorter the route, the fewer hills you will experience. Riders are generally quite happy with the route, and find it just challenging enough! 

I’m an inexperienced rider… will I survive?

Yes! We created the 25km option just for you. It may be a little challenging, but we believe in you!  

Can my children ride?

Kids are more than welcome at the Jack Ride, but only if they are keen, competent on a bike, and prepared for the challenge. We’ve had successful riders as young as 8 years of age, but for the average child rider, 13 years of age minimum is recommended. The route can be challenging and it includes a few big hills. So as with any rider, children should be signed up for the route that best suits their experience level, and always be accompanied by a parent or guardian.

Can my friends and family come to cheer me on?

Of course! The more the merrier. They can come cheer you on! We encourage friends and family to register as volunteers

How can I donate to Jack Ride?

For online donations (credit card, or Paypal), you can click here. Offline donations (cheque or cash) can be mailed to our office (192 Spadina Avenue, Suite 505, Toronto ON, M5T 2C2). For offline donations, make sure it is clear which rider/team you are sponsoring.

Is the fundraising minimum mandatory?

Yes! Jack Ride is’s largest fundraiser of the year and. It provides essential funds to support of youth mental health programs. We depend on every rider-raised dollar to fuel our network. 

What is the deadline for all the pledges to be in?

We ask that all pledges be in by Ride Day, but we will still accept donations after.

How do I register as an individual?

Click here and select “register as an individual”.

How do I register a team?

Click here and select “start a team” 

How do I join a team?

Click here and select “Join a team” 


Yellow Jersey Sponsor

Bank of America Merrill Lynch

Jack 100 Sponsors

Air Canada
South St. Burger Co.

Jack 50 Sponsors

Caledon Ski Club

Jack 25 Sponsors

Upper Canada College
Bike Right