Tailwind Cycling Tours - PEI

03/02/2026

Looking for something exciting to do this season? Are you retired and looking for a change of pace or a student looking for summer work? Are you willing to learn to become a bike mechanic? We are a fast growing bike shop in Stratford and we need outgoing and dynamic individuals to add to our team. We foster a fun and friendly work environment that's engaged with the cycling community, events and cycling tours. See why we are a perfect 5 star on Google business ratings. 🙂

Drop in and see us. Call, email or text if you are interested.
[email protected]
902-367-5191
41 Hollis Ave, Stratford PEI, C1B4A1

01/12/2026

As PEI's newest Cycling Tours Adventurer, we are proud to sponsor the 2026 edition of the Banff Film Festival.

Get your tickets now at Sporting Intentions.
Show times January 30 and 31st 7pm



Check out our cycling tour website
https://tailwindcyclingtours.ca

08/22/2025

Our group was treated to Julio's Oyster Bar before enjoying a tailwind rise back.



tailwindcyclingtours.ca

08/22/2025

Day 2 takes us to St Peter's Bay for some Oysters at Julio's.




tailwindcyclingtours.ca

08/18/2025

Not us but the event organizers of showcases some spectacular gravel rides on the other island of Newfoundland. If you want the ultimate gravel adventure then this is a must experience to add to your ride list.

The Rough Waters Gravel Grind registration is now open. Coming up on September 20th, this is a gorgeous romp through the woods on bike! You can do it on your mountain bike, your fat bike, but obviously if you've got a gravel bike then that's the way to go. Please note we also accept e-bikes of either of those models!

Come join us for either our 40km option, 70km option or 114km option*.

Follow the link to sign up, and if you're on instragam it's in our bio! https://ccnbikes.com/ #!/events/rough-waters-gravel-grind-2025

06/30/2025

Enjoy your ride up at Hillsborough. We'll see you when you get back from your ride to St Peter's and back.

Take advantage of our day trip with a rental of our Spherik Electric bike. It has a range of 80 km in one charge.

https://tailwindcyclingtours.ca

06/12/2025

Back by popular demand. The Red Hot Hilly Chily Graveler.

Register now and experience a unique gravel adventure on the hilly side of PEI.

There are two routes (a long and a short) to choose fromm one around 57km (start time 8am for slower riders, 9am for fast riders) and the other around 40km (start time 9am for all riders).

We will be serving post chili and drinks with your entry.

Registration on the link below
https://www.cyclingpei.org/events/red-hot-hilly-chilli-grinder-2025

Also visit your sponsors
https://tedsbikes.ca/
https://tailwindcyclingtours.ca/