Caledon Hills and Cheltenham Badlands

These two hikes I completed back to back. The first, Caledon Hills, was on January 11, 2026 and the second, Cheltenham Badlands, was on January 12, 2026. Both days were super windy which brought a nipping chill to the air but otherwise it wasn't too cold, as it sat around feeling like -10 degrees celsius. It's amazing how much the wind can add to the cold air. I have hiked in colder temperatures but they can feel much warmer than these days did and the only difference is the wind. Both of these hikes, I was lucky enough to have company which meant that I didn't have to hike out and back and that we had a vehicle sitting at the end of these hikes. Both of these hikes had quite a bit of road walking and was more lack luster than most of my hikes so far. Exciting news: these two hikes are among my last remaining ones in the Caledon Section. I have just one more hike to complete in this section.

Caledon Hills

For this hike I was very fortunate that Jared was able to accompany us. Specifically because it was

10 kms parking lot to parking lot, so if he hadn't come then we would have done 20kms there and back. This hike included a ton of road walking, which isn't ideal and is usually pretty boring, so it's nice that I had company. There's not much scenery to enjoy and then there is the added risk of vehicles driving by. It's quite common for the Bruce Trail to include road sections because it covers such a vast area of Southern Ontario, making it impossible to always stay within the wilderness. Normally, the road sections aren't quite as long as this one. Out of the 10kms that we hiked, at least 6kms were on the road itself.

The Challenges of Hiking Through Field and Bush

The remainder of the 4 kilometers was a journey through a diverse landscape that transitioned from open fields to dense bush. This segment of the hike presented a variety of challenges that tested our endurance and adaptability. The initial portion was through expansive fields, where the ground was blanketed in a thick layer of snow, creating a beautiful yet formidable terrain. Right from the start, we encountered significant snow drifts. As we ventured further into the fields, the experience quickly became a guessing game. Each step we took was fraught with uncertainty as we tried to predict whether our feet would remain on solid ground or plunge into the depths of the snow. This unpredictability added an extra layer of difficulty to our trek. Anyone who has traversed such snowy landscapes can attest to the frustration that comes with the constant anticipation of sinking. Jared had the privilege of hearing my expressions of either happiness or frustration and could determine if I had sunk into the snow. There were moments when we found ourselves wishing for our feet to sink completely through the snow rather than experiencing the jarring surprise of an unexpected dip which throws our balance off. In contrast, a deliberate step into a deeper drift, while challenging, would at least allow us to brace ourselves for the impact.

Cityscapes

While walking down the "Escarpment Side Road," we were treated to panoramic views of the sprawling urban landscape to our east, where several large cities lay in the distance. As I viewed the horizon, I never thought I'd be able to pick out the CN Tower. I completely thought it would be too far away. However, as I scanned the skyline, my eyes quickly locked onto the iconic landmark that is synonymous with Toronto. Excitedly, I pointed it out to Jared, who then proceeded in thinking that I was incorrect and it wasn't the correct location of the city. (Ensue eyeroll). Also I will point out that his eyesight is not as good as mine. In order to convince him, I grabbed my phone and decided to take a video of the skyline, ensuring that I zoomed in as far as I could on the CN Tower.

Intrigued by my ability to see the tower, I looked it up on Google and discovered that the CN Tower was approximately 65 kilometers away from where we stood on the Escarpment Side Road. This revelation was astonishing, as it highlighted the clarity of the view we had despite the considerable distance separating us.

Can you spot the CN Tower?

Obstacles

As we were walking along the path a sense of unease began to settle over me regarding how we would navigate the daunting task of crossing highway 10. Anyone who has ever driven on this road is well aware of how busy and fast paced this highway is. In this particular stretch of the highway, there are a total of seven lanes, which includes not only the main lanes for through traffic but also designated turning lanes that can add to the complexity and chaos of crossing safely.

The thought of attempting to dart across such a busy highway filled me with apprehension, as the potential dangers loomed large in my mind. It reminded me of when I had to walk along the shoulder of Hwy 9, which was busy enough and it only has four lanes. Mono Mills Winter Hikes. However, as we continued our walk, I was relieved to see that there was a well-lit tunnel designed specifically for pedestrians that ran underneath this hectic stretch of road. As we walked through this underground corridor, I couldn't help but appreciate the foresight of the planners who had designed such a feature, recognizing the need for pedestrian safety in an area dominated by vehicular traffic.

Obstacle #2

We reached one stile on our adventure. The Bruce Trail uses these to allow only humans and dogs to use the trail (motorzied vehicles, horses etc can't fit through). These stiles consist of a ladder for the humans to climb and a hole through a wire fence for the dogs to travel through. This particular hole in the fence was not large at all. In fact, I find that these openings are generally quite small to begin with, and when you factor in the additional snow that had accumulated, it became evident that this hole was even more constricted than usual.

Mia, our small determined companion, could fit through the hole by crouching down easily. Jared and I stood there, contemplating our options for Oliver. We considered lifting him up and over the fence, which would be a very difficult thing to accomplish. We eventually decided to convince Oliver to go through on his own. If he was unable to crawl through then we would find another way. After a couple of attempts, and with some patient encouragement from both Jared and me, he decided to give it a go and attempted to army crawl through the small opening. And trust me when I say, he was incredibly low to the ground as he wiggled his way through. Even with Jared pulling the wire fence up as far as he could, the space was so tight that Oliver had to flatten himself almost completely.

This experience showed how far Oliver has come on his journey. I distinctly remember our first encounter with a similar stile Duncan Caves and Snell Loop. The hole back then, while still small, was significantly larger than this one, and I had to do so much convincing to get him through. It took a lot of coaxing, and I could sense his hesitation and uncertainty. But now, seeing him tackle this new challenge with such confidence and resolve was truly inspiring. It was a proud moment for all of us, especially knowing that he had overcome his initial fears and was now willing to take on obstacles that once seemed daunting.

As we crossed the stile and walked along the trail, Jared looked to the right and announced that we could have went around the corner, down the side road and back in to the trail. This would have meant we avoided the stile all together. So, note to self, there is always another way!

We started this hike at 11 AM and finished by 2 PM, it took us three hours to do 10 km. The entire 10kms were a part of the main Bruce Trail which made a significant dent into my overall kms left for the Caledon Section.

Cheltenham Badlands

This hike was completed the very next day and serves as a continuation of our previous adventure along the scenic Caledon Hills.

I was particularly fortunate that my sister, Taylor, decided to join me on this hiking expedition. Having a companion on the trail truly enhances the experience as it gave us an opportunity for shared memories and moments of joy. Like I previously said, we were able to place a vehicle at the end of this hike which allowed us to extend our journey significantly, enabling us to venture much further than we would have been able to if we had opted for a simple out-and-back hike.

Forest and Road Walking

Throughout the day, our hiking adventure unfolded in two distinct terrains. Half of our hike took us deep into a forest, where we were surrounded by towering trees that stretched high into the sky. It was interesting to me that this entire hike was through deciduous trees (maples, oaks), so it appeared as we were just walking through dead forests. Most hikes that I have done, have had a nice mix of evergreen and deciduous. Obviously, evergreen trees are stunning in the winter as they hold the snow beautifully. The forest offered a diverse array of terrains that kept our journey engaging and dynamic. We encountered gentle slopes that allowed for a comfortable pace and very steep inclines that tested our endurance.

The atmosphere in the forest was particularly pleasant that day, as the snow from previous storms had been packed down considerably, creating a firm and stable surface that was easy to traverse. This was a delightful change from my past several hikes, where I had often struggled through deep, unyielding snow that sapped my energy.

The other half of our hike was on quiet roadways that allowed us to cut from one forest to another. These paths offered a welcome contrast to the rugged terrain we had just navigated. The roadways were smoother and more forgiving, allowing for a leisurely walk that felt amazing after the earlier exertion.

First Mistake

The start of the hike had quite a bit of inclines, which instantly made us warm as we began to exert ourselves against the challenging terrain. The initial steepness of the trail demanded our attention and energy, causing our hearts to race and our muscles to engage. It was a super windy day, with gusts that whipped around us, but the temperature felt like it was hovering around a brisk -8 degrees Celsius. The wind chill added an extra layer of chill to the air, making it essential for us to dress appropriately for the conditions. There were moments during our ascent when Taylor found herself removing her jacket to cool down a bit, while I took the opportunity to remove my hat and mitts, feeling the warmth generated by our physical activity.

As we hiked along, engaged in lively conversation, sharing stories and laughter, I was fully immersed in the experience. The trail wound through a picturesque landscape, with trees lining our path and the faint sounds of nature surrounding us. However, after about half a kilometer of hiking, I suddenly realized that we were supposed to make a turn at a specific point that I had overlooked. I had already hiked that part of the trail previously, heading into the scenic area known as the Forks of the Credit, a beautiful spot nestled in the heart of the Hockley Valley, which is famous for its stunning natural beauty and diverse wildlife. Hockley Valley, Forks of the Credit and Nottawasaga Lookout

As I processed this realization, this little oversight meant that we would be adding an unexpected extra kilometer to our long hike. We decided to embrace the situation, laughing off the mistake as part of our adventure. Luckily we weren't in any hurry to return home but decided after this mistake to check the app at every intersection/corner etc to ensure we were on the correct path.

Looming Hill

At one point during our leisurely stroll, we found ourselves meandering down a particularly quiet and serene road. In the far distance, a massive hill loomed, Taylor asked almost jokingly “Are we going to hike up that?” I pondered her question for a brief moment and replied, “Maybe, I guess we will find out.” As we continued to walk, the hill gradually grew larger in our view. As we got closer, it became increasingly clear that we were indeed going to tackle the ascent.

At the base of the hill, a daunting flight of steep stairs awaited. They wound around a bend, making it impossible to see all the steps we needed to conquer. In total, there were about 50 steps. It was a straightforward yet formidable task, with the stairs leading directly up the hill. Their worn surfaces revealed the passage of many feet before ours. As many had traveled this path before us, the snow had become icy and slippery, adding to the challenge as we climbed the hill.

With each step, the incline grew steeper, and we could feel our muscles working harder than they had during our leisurely walk. The rhythm of our breathing changed; what had started as a calm, steady pace turned into deeper, more laboured breaths. By the time we reached the top, there was no denying the physical toll of the climb; we were both sweating and panting heavily. Fortunately, it came to a plateau to offer our bodies a slight break from working so hard.

Conclusion

This hike was an incredibly enjoyable experience, filled with laughter and engaging conversation, as my sister and I chatted the entire duration of our trek. The time truly flew by, and before we knew it, we had already spent four hours on the trail, covering a distance of 14 kilometers. However, it's worth noting that we inadvertently hiked an extra kilometer that wasn't part of our original plan. Therefore, only 13 kilometers of our journey can be officially attributed to the main Bruce Trail, as I have already accounted for that additional kilometer in a previous hike.

The hike began in the Caledon Section of the Bruce Trail and concluded in the Toronto Section. This was my first time hiking into the Toronto Section of the trail.

As always, Thank you for reading,

Kendal

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