Trail running in Ontario is severely underrated. We have so much to offer when it comes to technical terrain, punchy climbs up and down, and stunning views across the province. While we might not have the mountainous mountains of BC, Quebec or Alberta, Ontario certainly has much to offer in providing a fun home for runners to seek solitude on the trails. Or to seek some wild, even dangerous, adventures. As I cap off my first year as a part-time pro trail runner, I countdown the toughest trail segments in Ontario.

CRITERIA

In order to qualify for this list, the segment in question must be predominantly on trail, and in the province of Ontario. That much might be obvious.

However, in writing this list as a sole entity, I am also only including trail segments that I have actually seen with my own two feet. That list is quite extensive, but ultimately incomplete. If you have any feedback on challenging trail sections I need to try, I would love to hear about them, as there’s nothing about this sport that I enjoy more than the challenging sections on the trails.

In terms of how these segments are ranked, much has gone into selecting the list. The Strava segments are ranked by danger, amount of thinking required, technicality, length, elevation profile, and collapsibility (that is…how much do you feel like collapsing once it’s done?). Ultimately, I’ve given preference to those segments that are the most dangerous and wild in technicality.

I’ve generally tried to exclude longer segments unless they’re part of a historic Ontario trail race; and flat technical sections have only been included in the way the race course intends it to be run. Ups and downs on the other hand may both be included. Finally, I’ve also given a slight edge to segments with an outrageous CR. If it’s dangerous and potentially lethal to try and beat, that’s usually a sign. With that, let’s jump into the list.

HONOURABLE MENTION: BORER’S FALLS DESCENT

Not to be confused with the blazing fast Reid Coolsaet CR from the top of the stairs near Borer’s Falls down toward the dog park. This is the more technical and dangerous way to descend from Borer’s Falls, heading toward Valley Rd. instead.

Despite this being a downhill, it’s incredibly difficult to run fast, so the CR is stuck at 5:26/km. You start down the narrow steps that are so narrow you basically can’t run, then you descend down a steep rocky section that requires constant readjusting of where to plant the feet. When you get out of that, you head toward another technical section with a massive fallen tree in the way, not to mention usually tons of mud. You end on one final technical portion toward a bridge before the segment ends and it goes back uphill. This is one that I haven’t even attempted to run fast out of safety precautions.

Location: Borer’s Falls – Bruce Trail – Burlington/Hamilton
Link: Borer’s Falls Descent | Strava Run Segment in Ontario, Canada

HONOURABLE MENTION: STARTED FROM THE BOTTOM, NOW WE’RE HERE!

Anyone who’s done Sulphur Springs knows that it’s a highly runnable trail race. Technicality is kept to an all-time low, and it’s perhaps one of the reasons why it’s such a competitive race for road and trail runners to come together. I’ll often discuss with other trail runners how the most difficult parts of the area are actually off-course. ‘Started from the bottom now we’re here!’ is unquestionably the most difficult part of the area (yes, more than K2 and ‘Singletrack next to RT’) and makes for a mean place to hill repeats.

It starts up a super steep uphill, and then goes through windy, narrow up/downs. I’m not sure where this created version of the segment ends, but one of the trickier parts of it comes near the logical end before you get to a runnable field. At that point, it’s hard to navigate through tall bushes without getting stabbed and cut across the legs. I’m also always afraid that I’m about to step on a toad, which adds another layer of technicality.

Location: Sulphur Springs / Dundas Valley – Ancaster/Hamilton
Link: Started from the bottom now we’re here! | Strava Run Segment in Hamilton, Ontario, Canada

10. UNICORNS ARE REAL

Unicorns are real takes place toward the start of the Falling Water Trail Marathon, in what ends up being one of the muddiest sections of the entire course. On race day this year, Dylan Pust and I hammered it through the mud, with the trail already torn apart by the early start the race allowed. We both had a few scary slips and spent most of the time just trying to stay upright.

But even in a dry time of year, the narrow, technical, winding nature of the segment makes it incredibly difficult to run fast. It crosses a few rocky river sections and ends on a wildly steep uphill. The CR is set at just 5:05/km, highlighting at least some of the wild difficulty.

Location: Falling Water Trail Marathon – Bruce Trail – Grey Highlands
Link: Unicorns are real | Strava Run Segment in Kimberley, Ontario, Canada

9. DOWN, DOWN, DOWN!

Okay, so this one is scary. It’s absolutely stupid to run this segment fast, given the tightness of the turns and the number of narrow trail stairs along the way. The guy that had the previous CR told me that he nearly killed himself doing his attempt, and I fully believe that given how quick your leg turnover needs to be in certain moments. The amount of thinking required is at a high degree, and it’s one of those segments that just isn’t smart to try and run fast.

Location: Mono Bruce Trail – 5th Line EHS Section – Mono
Link: Down Down Down | Strava Run Segment in Orangeville, Ontario, Canada

8. UP, UP, UP!

The reverse of Down, Down, Down! is Up, Up, Up! While it’s not quite as dangerous as the downhill, it gets bonus points for taking almost twice as long. As the name suggests, it just keeps going up, along many sections of trail stairs, tight turns, and steep grades. It’s definitely not a ‘runnable’ uphill, so the CR is set at almost 6:00/km. We don’t have many three-minute uphills across the province, and this is one that definitely takes its toll on the body.

Location: Mono Bruce Trail – 5th Line EHS Section – Mono
Link: Up Up Up | Strava Run Segment in Orangeville, Ontario, Canada

7. UP TO THE WATERFALL – SMOKEY HOLLOW

Most of the time that I’m doing Up to the Waterfall, I feel like I can relax. But it’s a long, gruelling four-minute uphill that does require you to stay focused and in-tune on where you’re planting your feet. There’s nothing particularly steep about any of the sections, although the stairs are narrow and winding and there’s plenty of technicality to go around. It’s equally gnarly to Up, Up, Up! in Mono, just a minute longer, even if not as steep.

Location: Smokey Hollow – Bruce Trail – Waterdown
Link: Up to the Waterfall – Smokey Hollow | Strava Run Segment in Burlington, Ontario, Canada

6. DOWNHILL FROM THE WATERFALL – SMOKEY HOLLOW

So if you think it’s tough going up, it’s even tougher going down. That’s because those narrow stairs and tough to navigate terrain become even tougher when you lack the same level of control in your body. I don’t think I’ve ever run it on the exact same way, since it’s so easy to get out of rhythm.

Most of the time that I visit Smokey Hollow, I actually start where this segment ends, at Grindstone Creek Ascent. I walk this downhill – simply because it’s safer. Not only is it difficult to run this segment fast, but with so many rocks, stairs and roots, it just wouldn’t make sense to do so.

Location: Smokey Hollow – Bruce Trail – Waterdown
Link: Downhill from the Waterfall – Smokey Hollow | Strava Run Segment in Ontario, Canada

5. 12A TO HOGG’S FALLS SOUTHBOUND

I’ll always remember Reid Coolsaet saying to me that Falling Water wasn’t that technical. The downhills that lead into Hogg’s Falls beg to differ. In many sections of it, it’s legitimately dangerous to run fast, as you’re right next to the cliff in a similar vein to Unicorns are real. There’s a flat section where you really can’t run at all because of all the oddly placed rocks, a climber that you’re better off slide tackling underneath than actually climbing, and then some absolutely wild downhills shortly before Hogg’s Falls. It’s all the roots alongside the windy steepness that make this section so difficult, and likely where Falling Water gets its branding as being more difficult than people expect.

Location: Falling Water Trail Marathon – Bruce Trail – Grey Highlands
Link: 12A to Hoggs Southbound | Strava Run Segment in Grey Highlands, Ontario, Canada

4. EUGENIA FALLS

After a long historic climb up ‘Cuckoo Valley’, the Eugenia Falls segment takes place on what I call the ‘Choose Your Own Adventure’ section of Falling Water, where there is no right or wrong place to put your feet, so long as you don’t go over the falls.

It’s a ton of rocks and roots oddly placed into the ground, and even muscle memory and familiarity fail to fully help. Being part of an aid station may be part of the equation here, but the CR I set during this year’s race is at 6:23/km. On top of all the technicality, it ends with a steep, winding climb to the top of the falls. It’s not quite dangerous like some of the others, but it’s tricky enough that most runners wouldn’t even bother to run through it.

Location: Falling Water Trail Marathon – Bruce Trail – Grey Highlands
Link: Eugenia Falls | Strava Run Segment in Grey Highlands, Ontario, Canada

3. SHARPES CREEK LINE TO BOUNDARY BRIDGE

First of all, the Maitland Trail’s segments are great because they’re aptly named by what section of The Bad Thing you’re actually covering. Second of all, this is by far the most difficult section of the entire race, because it’s so incredibly technical. It definitely checks that box of being difficult to run fast out of fear for the danger, as you’re persistently swarmed by these narrow and windy stair sections. You’re crossing rivers, navigating rocky root terrain, and then trying to navigate the leaves, which cover the trail in the Fall when The Bad Thing takes place.

I’ve only experienced this during the Fall, but one of the worse parts (or more fun parts) is the fact that the trees are not well marked, and so it’s difficult to tell where to even go when the leaves make it so you can’t tell naturally.

But back to those stairs – they’re always down these super steep downhills and incredibly uneven. For all the difficulty of the Smokey Hollow Waterfall Downhill, you’re running on stairs that are relatively consistent in where to step, both in angle and proximity away from the next. The stairs on the Maitland are built absolutely horribly, and I love it so much.

Location: Maitland Trail – Goderich/Auburn
Link: Sharpes Creek Line to Boundary Bridge | Strava Run Segment in Clinton, Ontario, Canada

2. RAT JAW DESCENT

Just about every trail runner in existence knows what ‘Rat Jaw’ is – the famous uphill segment in the Barkley Marathons where you get stabbed by thorns. Our own version in Ontario is no joke, especially since it’s so incredibly steep.

The steepness alone is what makes this segment so dangerous to descend. You’re descending 70m in as little as 200m of running, across an average grade of -38%. Anyone who wants to go for this CR is crazy. In fact, I feel crazy every time I do it. I typically descend down Norman Pearson (Grindstone Creek Descent) instead, and only save this for special occasions because of how much it destroys the body. That seems crazy to say, because it’s by far the shortest segment on this list – lasting only a minute for those wishing to go for the CR. The length is ultimately why I’ve ranked it second here.

But again, this is no joke. You simply can’t control your body at the rate you’re propelled to descend, and then toward the end, you have to shuffle jump to the right to ensure you hit the gap in the trail as it veers off to the right. You’re not exactly getting stabbed by thorns, but you’re definitely colliding with some sharp bushes along the way nonetheless.

Location: Smokey Hollow – Bruce Trail – Waterdown
Link: Rat Jaw Descent | Strava Run Segment in Burlington, Ontario, Canada

1. RAT JAW

It’s downhill counterpart might be more dangerous, but more effort and mental preparation ultimately go into tackling this uphill. I can’t imagine any uphill being this steep anywhere else in our province, not least one that lasts at least a minute. There’s literally no way of tackling it without wanting to collapse at the end. Even hiking it gets my HR wilding out over the grade. The CR is set at 8:07/km, broken this year from the previous CR that was set at 9:30/km six years prior. Good luck running the entire thing, and good luck not collapsing at the end. It’s that brutal.

Location: Smokey Hollow – Bruce Trail – Waterdown
Link: Rat Jaw | Strava Run Segment in Burlington, Ontario, Canada

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This list will be updated as I continue to explore the trails across our beautiful province. For the time being, if you have any suggestions for technical or gnarly trail sections that I need to check out, please feel free to let me know! My favourite part of trail running is all the difficulty, and the requirement to focus and stay locked in on what you’re doing. I’d love any suggestions for where I can do exactly that across the province. Thanks for reading and see you soon!