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2021 Cycling In Ontario Guide

Locals Share Top Bike Rides in Waterloo Region

If you are a keen cyclist chances are you know the best routes in your neighbourhood, city and surrounding area. Hence who better to ask than local riders for their favourite rides and destinations in Kitchener, Waterloo and Cambridge areas for some great fall cycling.

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The Happy Stragglers: Ride Experience, Community and Gravel at Reggie Ramble 2021

Oct Blog Reggie Ramble

When my partner Natalie and I decided to sign up for the Reggie Ramble, a self-described “gravel grinder” event, we were admittedly both a little nervous. While we are pretty experienced cyclists the sustained output required to participate in a bike “race”, especially on gravel, soon had us questioning our decision.

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Ontario By Bike Photo Contest

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Ontario By Bike's 2021 photo contest is open for submission. Click below to learn how to participate in the contest and to see all the great winners and honourable mentions from previous years.

Click HERE for more information.

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Ontario By Bike Blog

Blog coverCredit: Destination Ontario

Read on for inspirational cycling experiences across Ontario. Whether you're looking for rail trails, mountain biking or road riding, we're putting together stories to get you out on two wheels. Join us on Facebook, Twitter and Instagram to get more updates and so we can hear your story. Interested in guest blogging with Ontario By Bike? Shoot us an email!


4 minutes reading time (868 words)

Chipping Away At The Caledon-Lakeside Ride

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When cycling enthusiast and photographer Martin Lortz learned of the nine cycling loops showcasing the Great Lakes Waterfront Trail and the Greenbelt Route, he first thought, that's pretty cool. After a bit more research, a goal for the season solidified, to ride and check all these loops off the list. Discovering that one of the rides could be practically accessed from his front door and with riding season just around the corner, he thought there is no better time than now, and recently got rolling.

A Great Lakes to Greenbelt Cycling Adventure

The Caledon-Lakeside Ride showcases the Mississauga and Oakville waterfront, the Greenbelt route between Georgetown and Caledon and the Etobicoke Creek Trail. At 173 kilometres, it is recommended as a two-day ride with an overnight in Georgetown. With scheduling conflicts and a cycling partner, aka my wife, who is still building her in the saddle endurance, even an 80+ kilometre day can seem more like work than fun. Determined, we opted to take advantage of the numerous access points along the route to achieve our goal in several day rides.

Caledon Lakeside ride collage
Photo Credit: Martin Lortz

Ride One

As it turns out, our goal to complete the Caledon-Lakeside Ride started even before we knew it as our last ride from the Ken Whillans Resource Management Area to Glen Williams along the Caledon Trailway is part of the loop. A delightful ride along the rail trail, then on to quiet roads and Glen Williams. The road section offers a glimpse into the rolling hills you can expect along the Greenbelt portions of this loop. On the way back, we made a slight detour to Spirit Tree Estate Cidery for a bite to eat and some liquid refreshments to take home with us.

Caledon Lakeside ride orange leaves
Photo Credit: Martin Lortz
Caledon Lakeside Ride Bridge Crossing
Photo Credit: Martin Lortz
Caledon Lakeside ride follow the creek
Photo Credit: Martin Lortz

Ride Two

Ride number two has us back at Ken Whillans Resource Management Area, but this time it's just a drop off as the plan is to ride back to Lake Ontario along the Etobicoke Creek Trail; starting on the rail trail, then on to country roads, and then south on bike lanes along Kennedy Rd. We pick up the Etobicoke Creek Trail at the north end of Brampton. From here on, the majority of the ride is along a paved multi-use trail zigzagging through ravines and parks. Following the water flow, the day has a slight downhill slant to it, making for pleasant pedalling even if, at times, it might not feel like it. There are many opportunities to purchase food and drink along the route or stop for a rest. Our only challenges on the day that added a few extra kilometres to the tally were the go-arounds required to bypass construction on the Hwy 401 and QEW underpasses. A 60-kilometre day and definitely a pleasurable ride discovering such fantastic cycling within city limits.

Caledon Lakeside ride circle the pond
Photo Credit: Martin Lortz
Caledon Lakeside Ride urban stretches
Photo Credit: Martin Lortz
Caledon Lakeside Ride Lake Ontario Views
Photo Credit: Martin Lortz

Ride Three

The southern section of the Caledon-Lakeside Ride along the Great Lakes Waterfront Trail can be accessed by Go Train from the Longbranch and Oakville stations. So the plan for ride number three is to cycle between the stations mentioned above, returning to the start via the Go Train. At just over 30 kilometres, the ride is a reasonably short one. That said, with many distractions along the way, it is easy to make this quick tour into a full day outing. Lake views, parks and beaches vie for our attention. Port Credit and Oakville offer up an array of cafes, eateries and patios; luckily, the activity of cycling pairs nicely with the pleasure of eating. Some of our favourite highlights include Lake Promenade Park, Snug Harbour and Tannery Park in Oakville. A point to consider, this ride can be accomplished in either direction; perhaps the final decision needs to be made as to the direction the wind blows.

Caledon Lakeside Ride - Greenbelt Route Sign
Photo Credit: Martin Lortz

Ride Four

Back at the Oakville Go Station. We reconnect with the route at Tannery Park and follow the Waterfront Trail east to Forth Line. Here we turn north and cycle along bike lanes and trails north. A short hike a bike at Glenorchy Conservation Area Ravine and then on to the Greenbelt's rolling hills. Today's effort is fueled by the promise of the ride's end in the hamlet of Glen Williams in Halton Hills. A charming town noted for its visual artists, artist's studios and heritage buildings. The outdoor patio at the Copper Kettle Pub is a perfect spot to celebrate the end of a day's ride and the completion of the Caledon-Lakeside ride while waiting for our shuttle home to arrive.

from the great lakes to the greenbelt

Nine cycling loops showcasing the Great Lakes Waterfront Trail and the Greenbelt Route, yeah, that's pretty cool! The Caledon-Lakeside Ride is a fabulous cycling experience, no matter how you get it done. We might have chipped away at it this time around, but will for sure plan an overnighter next time.

  • Check out the Caledon-Lakeside route and download GPS files - Caledon-Lakeside Route
  • Find more information about the 3,600km long Great Lakes Waterfront Trail - Waterfront Trail
  • Discover the 475km Greenbelt Route and find day and multiday itineraries - Greenbelt Route

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