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New Summer Humdinger Bicycle Tours

Lake Kashawagigamog

Newly expanded trip options to meet the growing interest in summer vacations that can accommodate physical distancing include an Orillia Pedal, Pints & Pubs tour. Additional tours offered include Bruce County and new single day tours.


A New Spin on Stratford

If its been a while since you visited Stratford you may want to consider exploring the great outdoors this summer, starting on your bike! Create your own path to experience Stratford, or discover one of the many road cycling routes and trails nearby.


2020 Cycling In Ontario Guide

2020 Ontario By Bike Photo Contest


Ontario By Bike's 2020 photo contest is now open for submission. Whether it's in a winter wonderland, the season of bloom, the heat of summer or the cooler temperatures and colourful fall foliage, take a break and snap a few great photos featuring you and your bikes as well as places you stop.

Click HERE for information about submission and last year's winner.



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York Durham Headwaters

Waterfront Trail Ajax Waterfront Trail Ajax Photo Credit: Town of Ajax

Regional Cycling Events

Below you'll find a list of 2018 cycling events that feature York Durham Headwaters' destinations. You'll also find a link to the cycling resources found throughout the region.


Bike The Creek - June 23 - Ride the 5th annual Bike the Creek ride. Choose from 4 routes ranging from 11 to 40 km. Enjoy pavilions enroute where participants can learn about the natural and cultural heritage of the area. Participants have an opportunity to win prizes and will enjoy a complimentary lunch courtesy of the Region of Peel.

24 Hours of Summer Solstice - June 23-24 - Experience the summer solstice on two wheels at this mountain bike festival and relay race. The newly improved 17 km loop of single and double track trails is suitable for riders of most ages and abilities. Ride solo, tag team or with 4-10 people. A no night option is also available.

Rael's Ride - June 24 - Head to the North Thornhill Community Centre for Rael's Ride, a 25km/60km charity ride with a BBQ lunch and concert by the Practically Hip, Canada's #1 Tragically Hip tribute band. All to raise money for the Gord Downie Fund for Brain Cancer Research.

Ride Don't Hide (Peel Dufferin) - June 24 - Join communities across Canada and cycle together to raise funds for mental health. The Canadian Mental Health Association’s annual Ride Don’t Hide in Caledon features 5, 10 and 20km family friendly trail rides, as well as 25, 50 and 100km road routes.


El Bandito - July 21 - El Bandito 140 is back for 2018! It is part of the StuporCross series with the Eager Beaver 100. Let’s be clear though, this will be a completely different course. Great scenery, some challenging stuff and unique trails that you didn’t know were there await. And new for 2018 there is a shorter gentler course option for those who think that having fun and enjoying scenery doesn’t have to involve untold pain and suffering.

R4WS - RIDE 4 Williams Syndrome – July 29 - Ride in the 4th annual charity bike ride which takes off from North Woodbridge through King City and loops around Aurora back to Woodbridge.

Friends For Life Bike Rally – Join a one-day ride from Toronto to Port Hope (108km) on July 29th or join over 400 cyclists ride the Waterfront Trail from Toronto to Montreal – 600 km over 6 days. This 20th annual event which raises funds for people living with HIV/AIDS, is set for July 29th to August 3rd, 2018.

Great Waterfront Trail Adventure 2018- July 29 to August 3 - Join the 11th annual GWTA for 40 -110km (25 - 68 miles) of riding per day as we travel along the Great Lakes Waterfront Trail from Ajax with it's beautiful off road trail to the Quebec border and a finish line celebration with more than a slight nod to the Celtic traditions of South Glengarry.

Ontario By Bike Ride - Uxbridge Kawarthas Rail Trail - July 28-29, join Ontario By Bike on a weekend-long small group tour along a 100km+ rail trail network through the heart of the Kawarthas. This self-guided, supported tour is a 2 day / 1 night linear route from Uxbridge to Peterborough (or on to Lakefield).


Ride4UnitedWay - August 12 - Join the annual Ride4UnitedWay! A mass start from Whitby at 8:00am with 3 distances of 60km, 100km and 160km. A fully supported ride with on course support including food, hydration and check points. Bike mechanics will be on duty. Lunch, showers and massages at the finish. $60 before July 1st.

Ride for Karen - August 12 - Ride with cyclists from across Ontario for the 16th annual Ride for Karen, an annual fundraising ride to send children with cancer to camp. The fully-supported cycling event features a century ride (160km), along with 100km and 200km distances. Started in 2002 as a tribute to Karen Tobias who passed away from breast cancer, 100% of proceeds from the ride are donated to charity.

Highway of Heroes Bike Ride - August 25-26 - Wounded Warriors Highway of Heroes Bike Ride will take a group of Canadians along this sacred stretch (CFB Trenton to Queen's Park) to raise funds and awareness for those living with occupational stress injuries like Post Traumatic Stress Disorder. Honour the Fallen, Help the Living. Minimum fund raising required with 160 and 220kms route options available.


Skytop Beer and Bike Fest -  September 8 - Head to Scugog in Durham Region for a day shredding through beautiful trails? How about testing some sweet bikes, awesome food, local craft brewers, skills clinics, group rides, contests and some great live music to end the day!

Tour de Headwaters - September 15 - Ride in this 3rd annual event takes place in Caledon and the hamlet of Inglewood as the Start/Finish location for the 101.5km, 50km road routes and a 25km “family friendly” trail route.

Barrie 2 Baycrest - September 16 - Celebrate the 23rd annual Barrie 2 Baycrest ride. Travel through scenic countryside north of the city, and experience a convivial atmosphere and post-ride festivities. Riders can choose between a 100km or 50km route. Costs include limited edition jersey, breakfast, lunch and two tickets to post-ride dinner.

Uxcycle - September 23 - Head to Uxbridge to participate in the 2nd annual Uxcycle. All routes will start and finish in beautiful Elgin Park in the heart of Uxbridge. Ride options include 2 mountain bike trail loops (12km and 20km), 2 road cycling loops (54km and 25km) as well as an awesome family fun loop within the park. Live music, great local food, local craft brewery and many other businesses in the marketplace for good times after the ride.

Gianni Giro - September 23 - Join the 5th Annual Gianni Giro in King City. Get ready for another year of great cycling, as riders will be able to choose from 5km, 45km and 90km distances and finish up at a highly charged fun fair and bbq.

Markham Cycling Day & Tour de Markham - September 23 - Now in its 11th year, Markham Cycling Day is York Region’s largest public cycling event. It features the Tour de Markham, comprising of 10km, 25km and 50km cycling routes across the City open to youth, adults, seniors and families. It also features bicycle races for children and youth ages 3-10. In addition, a meal, give-a-ways, raffle prizes and entertainment. All events are FREE!


Sausauge Suit ITT - October 23 - A sanctioned time trial mountain bike race on a 15km or 30km course in Dufferin County Forest.  

Regional Cycling Resources

Durham  Peel
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