Ontario By Bike Ride – September 2025
This ride is now over.
The detailed itinerary for this ride is available below for download. Enjoy great road and trail riding on a self-guided ride experience.
Caledon Trails & Backroads Explorer
When: Anytime. It’s a self-guided itinerary
Duration: 2 days, 1 night
Ontario By Bike Ride Hosted: September 27/28, 2025
Total Distance: 122km
The Ride: Discover the charming small towns, trails, and backroads of Caledon, a rural region set against the striking topography of the Niagara Escarpment, just outside of Toronto. This ride starts out from Brampton on the Etobicoke Creek Trail, leading to Caledon’s pastoral roads and signature rail trail enroute to Georgetown for the night. On this ride pedal on a mix of forested trails, stunning paved and gravel roads, passing horse farms, forests, historic villages, and unique geographic sites like the Cheltenham Badlands. See another side of Ontario just outside the big city.
Experience Level and Ride Guide: Moderate to experienced. Riders on this ride need to have experience riding on roads with vehicle traffic and be comfortable with a few challenging climbs and descents, as this ride does climb and descend the Niagara Escarpment. Not all roads have bike lanes or paved shoulders to ride on. Some of the route is on very quiet country roads, other segments may be busier. The off-road rail trails, are a mix of hard packed limestone screening and some paved sections there are also some gravel roads included in the route. Suitable for gravel, hybrid and mountain bikes and road bikes with wider tires.
View Digital Routes:
FREE digital route navigation courtesy of our Ride with GPS Tourism Account. Using the links below, and downloading the Ride with GPS app on your mobile device, you can enjoy full turn by turn directions for each route using a free Ride with GPS account.
Day 1 – ridewithgps.com/routes/49422645
Day 2 – ridewithgps.com/routes/49459018
Day 1: Brampton to Caledon East to Georgetown – 66km
Beginning in bustling downtown Brampton, quickly joining the Etobicoke Creek Recreational Trail as it follows the creek through parks, urban forests and wildflower fields to north end of the city. Cycle past the city limits and into the town of Caledon (a rural collection of towns and villages) along Kennedy Road’s paved shoulders, as built-up areas swiftly turn to quiet countryside. Connect with the Caledon Trailway, which forms a spine connecting many of the area’s charming communities. After lunch in Caledon East, continue west along the trail through forests, open fields and the beautiful wetlands at Ken Whillans Conservation Area. At Boston Mills, detour off the trail to acclaimed Spirit Tree Estate Cidery, set on a stunning rural property with picnic tables, full market and restaurant with food and beverages. Continue on following the trail, also a part of the Greenbelt Route, and onto winding rural roads into Glen Williams and on to Georgetown for our overnight in Georgetown. Consider staying overnight at a certified bicycle friendly accommodation in the area. Our Ontario By Bike Ride group stayed at the Best Western Halton Hills.
Day 2: Georgetown to Inglewood, Cheltenham, return to Brampton – 56km
The second day’s ride begins on scenic country roads, along the Greenbelt Route and north through the Terra Cotta Conservation Area. Make a stop at the quaint Terra Cotta Country Store for a baked good and coffee. Bring your climbing legs as next we head up the Niagara Escarpment on a mix of pavement and gravel and what is surely some of the best scenery in the area, and past some of Caledon’s signature horse farms. Roll back down the escarpment and make a stop at the otherworldly Cheltenham Badlands, one of Ontario’s geological treasures, a unique and most scenic formation of exposed iron-rich red rock. Head into the charming village of Inglewood for your lunch stop of the day. Make your way south through the historic village of Cheltenham, before returning to Brampton on country roads and city trails to end off a fabulous two days of riding.
Additional Visitor Information:
Use below to find out more about ride areas and plan an extra day or two to see more.
- Ontario By Bike Peel & Greenbelt Areas – www.ontariobybike.ca/peel
- Visit Caledon – www.visitcaledon.ca
- Experience Brampton – www.brampton.ca/tourism
- Experience Halton by Bike – www.halton.ca/The-Region/Explore-and-Enjoy-Halton/Experience-Halton-by-Bike
- Greenbelt Route – www.ontariobybike.ca/greenbelt-route
Getting To/From Start:
The Brampton start location is about a 45 minute drive northwest of downtown Toronto.
The ride start location in downtown Brampton is conveniently located near the Brampton Innovation District GO Train and Bus station, on the Kitchener and Milton line, if you wish to take public transportation to the start location with your bike and luggage. Consult GO Transit for train and bus schedules.
The exact start time and location will be sent to all riders two weeks prior to ride.
This is an out-and-back ride with one overnight in Georgetown. You will park your vehicle at our designated and authorized group parking location in Brampton. Luggage transfer is included – from the start we will take your luggage to the hotel and return it to finish the next day.
Arriving Early / Staying Late:
Consider an overnight option at one of Ontario By Bike’s certified bicycle friendly accommodations in the region here.
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See our other 2025 Ontario By Bike Rides
Photo credits: Richard Oldfield (top); John Bachmann (middle-left); Ontario By Bike (middle-centre & middle-right).