Bobcaygeon, ON – They say “it’s a Jeep thing, you wouldn’t understand.” I’ve always admired Jeep’s commitment to stubbornly doing things their own way in pursuit of a highly specific, often intangible target, but have personally never quite understood the Jeep thing myself. Naturally, I was intrigued when Jeep invited me to an off-roading exercise to make me understand what the brand is really all about.

The event was hosted in Bobcaygeon, a beautiful little cottage town Northeast of Toronto, nestled in the Kawartha Lakes, right at the base of the rocky Canadian shield. The entire area to the south is flat farm land, but this is all lakes, rivers, forests, and ancient rock formations. It’s a popular area for the four-wheeling crowd, as there are trails all over the place, and the diverse terrain and often finicky weather makes things very, very challenging. 

Or at least, I thought it would be challenging. Parts of it looked impassable. This is how I learned Jeep is serious about their mantra of “go anywhere, do anything.”

Our convoy of vehicles weren’t anything special. They were showroom-stock Jeep Wranglers and Gladiators, a deliberately diverse spread of trim levels, body styles, and powertrains, meant to demonstrate that a) they’re aware that freedom and customization are core tenets of their consumer base, and b) any of these vehicles can handle this, and handle it easily. The most striking thing to me was seemingly how little concern Jeep had about their vehicles.

Not to say that they were careless, but I’ve been to other off-road events that were much more structured, with much more hand-holding, as you’d expect from a company trying to make sure a gaggle of hungover journalists don’t wreck their products. Not so much was the case here – it was pretty much just “alright, try and follow my line, let’s go.”

There are parts of this trail that I would have been uneasy about traversing on foot, let alone in someone else’s brand new truck. On more than one occasion early in the day I approached a steep rock face, a two-foot vertical step, and asked “are you… are you sure? This doesn’t look right.” 

If I hadn’t watched the lead Gladiator crawl up and over without even slowing down, I wouldn’t have thought it was possible. My feeble little car-brain raised on vintage sport sedans couldn’t comprehend that this was doable at all, and was even more floored that it was made almost a non-event by the unbridled prowess of a Jeep doing Jeep things.

“You’re gonna hear some very expensive-sounding noises today. Don’t worry about it, that’s the skid plates and rock rails doing their job.” No kidding; that’s from Aleks Tonkovich, the director of vehicle development for the Jeep Wrangler and Gladiator. He proudly has “the coolest job in the world,” and didn’t flinch at any point watching a bunch of amateurs bash his babies on boulders. He’s done this once or twice before, I guess.

The long wheelbase Gladiators were riding on their protective barriers all day, and even the four-door Wrangler Rubicon that I was piloting made more than a few sickening crunches as it crawled over the abutments of the Canadian shield. No one from Jeep seemed to care at all; this is exactly what these things were made to do. 

They were so confident in their vehicles that the lunch they planned was deep in the woods, accessible only by the same trails we were on – so they loaded a Gladiator Willys full of food and sent it along with us. It even got stuck on a particularly brutal obstacle, turtled on a big boulder. The factory Warn winch made it a non-issue. Anyone in PR knows you do not gamble with the media’s meals; the fact that they put lunch on the line is the ballsiest show of confidence I have ever seen in this field.

They’ve got reason to be confident. Things are looking up for Stellantis as a whole, and Jeep specifically.

Before the day got underway, Mike Szymkiewicz, head of product planning for Stellantis Canada, addressed our group with some very candid remarks. It’s no secret that their previous leadership made some pretty crucial mistakes, and there’s no shame in admitting that now, as he’s proud of where they’re heading.

“(Stellantis) feels like a completely different company from just six months ago.” They’re extremely confident in their new leadership in the form of CEO Antonio Filosa, who is apparently much more flexible than his predecessor and willing to listen to the people around him. “It was frustrating because you couldn’t do things for your market; Antonio has flipped the switch on that.”

Along with a $3.2 billion dollar investment, Jeep has some crucial product coming up to further bolster the brand and, uh, ‘pave’ the path to greener pastures. The new 2026 Cherokee – which you can order now, by the way – will fill a gaping hole in their product portfolio. The Grand Cherokee and Grand Wagoneer are both due for refreshes, and the Recon, a fun-sized Wrangler-esque EV, is coming very soon. 

More importantly, there’s been a reset on their pricing structure for most trims of Wrangler and Gladiator, with some trims being as much as $11,400 cheaper for 2026. “Pricing… maybe got a little away from us. We know that now, and we’re fixing that.” The authenticity of it all was really refreshing.

That authenticity is the foundation of Jeep’s DNA, their whole reputation is staked on it. In the past, a more cynical version of me might have dismissed Jeep’s appeal as being rooted solely in brand power, and there remains a lot of truth to that, but the appeal comes from the legitimacy of what’s underneath it. Your Bikini Blue Wrangler Sport might never see more Earth than a beach, but the knowledge that it will never get stuck on that beach is what makes it cool.

There’s so much to be said about the Jeep brand, about their history, about their history, about their commitment to their customers, about the whole culture that follows them. They’re almost like Harley-Davidsons in the sense that yes, there are perhaps more conventional ways to design and build a vehicle, but it would lose its identity in doing so. That distinct individual identity and the authenticity of the hardware underneath it is what makes it the icon that it is.

Seeing these Jeep Wranglers and Gladiators in their element, doing what they do best, was transformative. I think I get the whole Jeep thing now.