Cycling has always been a way to bring communities together. Whether that's making longer journeys accessible, or bringing likeminded athletes and enthusiasts together.

Troublesome wants to create a space for new and seasoned cyclists alike to ride together without barriers. We don't expect you to have a carbon road frame, or wear your spandex racing kit (but we think it looks great on you).

For us its about giving ourselves an excuse to get up early, enjoy the sunrise and put some miles on our tires to feel refreshed and renewed from week-to-week.

Our long-term vision is to focus on endurance/tour riding rather than racing, so if this sounds like you, we'd love to have you!

The Details

Our first ride is TBD, but we will be riding Thursday mornings meeting at the Troublesome Shop (1090 College Street, Toronto, Ontario) at 06:00 AM. We encourage riders to come about 10 minutes early so that we can get on the road as soon as the clock strikes. 

After each ride, we invite our cyclists to pop in for an espresso to start their day off right.


When are you starting?

TBD – but soon!

I've never ridden with a group before, will I be able to keep up?

Troublesome Cycling Club isn't meant for those who are racing for the finish line. We try to keep the pace around 20-23km/ph to keep it feeling like a workout, without making it stressful for new cyclists.

Are you guys on Strava?

Absolutely, find us here.

How long are the rides?

We keep our rides to 1:30h, which translates to roughly 30km. This gives us enough time after the ride to decompress before work and enjoy a cup of espresso.

What is the route?

Follow us on Instagram or join our mailing list to be the first to know.
More details coming soon!

How much do memberships cost?

We're happy to take on anyone who wants to join, without having to worry about paying for a membership fee. We do recommend our club members purchase and wear a Troublesome Cycling tee (because we want to show the other clubs we mean business), but for the time being, we're just happy you showed up.

What do I need to bring to each ride?

All you need is a bike, a helmet and your game face.

How do I know a ride is happening this week?

We'll post on Instagram if there are any changes to our schedule, whether that's cancelled rides due to inclement weather, or bonus rides throughout the week. 

How do I join?

You'll need to sign a waiver before you can join us on our first ride. Then just show up 10 minutes before a ride and introduce yourself! If you have any other questions, you can just email us at