Presented by

Caledon, ON

Join us for Jack® Ride 2026

Road and Gravel Routes

Our Jack Ride committee works hard to design the best routes for various skill levels. Below are the 2026 routes and are subject to change.

If you have any questions, please email ride@jack.org

Register now

Jack Ride 25km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! Suitable for families and new Riders. Slightly less hilly than last year, still manageable for new and young Riders. Will take approximately 1 to 2.5 hours depending on individual pace.

Jack Ride 50km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! A reasonable challenge for youth, families, and inexperienced Riders. Some hilly terrain, though less overall than last year. Will take approximately 2-4 hours depending on individual pace.

Jack Ride 75km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! For experienced Riders. Several pace groups. Hilly terrain, though less overall elevation than last year. A good challenge for experienced Riders. Will take approximately 2.5-4 hours depending on individual pace.

Jack Ride 100km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! For experienced Riders. Several pace groups. Hilly terrain, though less overall elevation than last year. A good challenge for experienced Riders. Will take approximately 4-6 hours depending on individual pace.

Jack Gravel (2025) 40km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! For experienced Riders. 3-4 pace groups. A great mix of surfaces, with a little more elevation than last year. A good challenge for Riders new to gravel. Will take approximately 2-3 hours depending on individual pace

Jack Gravel (2025) - 80km

*This route is subject to change*

The start and finish line is at Caledon East Community Complex.

All new territory for Jack Ride to explore! For experienced Riders. 3-4 pace groups. A mix of rail trail, forest track, gravel and asphalt, with a tad more distance and elevation than last year. A good challenge for Riders familiar with gravel. Will take approximately 4-6 hours depending on individual pace.