*Our 2022 season has ended! Next season begins June 2023*

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

Troublesome aims 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.

For us it's 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 focus is more on endurance/tour riding rather than racing, so if this sounds like you, we'd love to have you!

The Details

Our rides are 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.


How do I know when your events are?

Join our Strava group to be notified of all upcoming events. Also be sure to follow us on Instagram, as we post updates there as well.

What style of ride is this?

Causal (no-drop), meaning no one gets left behind should a rider not be able to hold pace, if they have a mechanical issue or flat tire.

 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?

Our current route is 25km and we buffer 1hr 30min. This gives us enough time to accommodate different skill levels and also 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.

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, front/rear lights and your game face. (We also highly suggest sunglasses as that early morning sun can really blind ya)

How do I know if a ride is cancelled?

We'll post both on Strava and 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 hello@troublesome.co.