The Trail That Time Forgot: Two Days at the Ossewa Trail Run

Paul Ingpen
2 hours ago
4 min read

Not too many events can claim to have sold out in just their second year. An image of runners heading through a buffalo reserve then up through a steep sandstone crack to a magic view of the Drakensberg escarpment caught our interest, so we travelled to the eastern Vrystaat to catch a taste of what was being served to the very happy-looking trail runners.

For those of us from further afield, the drive from Jozi airport down the N3 is a scenic and simple one. As you head away from the city, the undulations turn steeper until the veld gives way to sandstone cliffs — very often flat-topped ones — which is so characteristic of the area around Harrismith. Cosmos flowers of blue, white & purple abound in the high yellow grass until you hit the final stretch on sand farm roads, where fat happy cattle & the odd wild animal graze, watched by birds of prey adorning the old farm fences and hunting the insects that grow louder as the sun sets.

I enjoyed a fun road trip with my friend Sipho and his 8-year-old son Mpho, who were returning to their roots to develop a family farm in the old Transkei. They love the outdoors & rare time out together, so this was a special reunion weekend away for the three of us.

Our arrival at the farmer-friendly registration, among the burning fires and nervously excited voices, signalled the start of a two-day jol among our favourite community. Trail runners are chilled; there was no talk of goal times or shoe choices. It was pure countryside stoke, and we were amped to be immersed in it.

What makes the biggest first impression is the scale of the Ossewa race village. Rows of glamping and canvas tents surround a large dam that twinkles with lanterns & reflects the mountain silhouettes and bright fires burning in the social lapa. The calm pond also amplifies the giggles & singalong sounds of the 500 runners & families enjoying this remote farm in a hidden valley that you are unlikely to ever explore if you didn't run the Ossewa trail run.

The farm-fresh food filled our tanks, & a comfy night in a big tent with real linen & warm blankets prepped us for two days of adventure, running high up on the mountain tops surrounding the valley.

Misty mountains are a thing — a natural smoke machine that welcomed the dawn each morning. It was brisk at night but warm by day. As the sun rose, the mist cleared and what were only distant silhouettes by night grew into enormous cliff-faced walls, which struck both fear and intrigue as we rolled up to the sun-soaked start line, full of fireside coffee & local liedjie-inspired energy.

Day 1 is the big day — a 24km queen stage, so to speak. First, we snaked our way up a zigzag path through the buffalo reserve to the base of the Kerkenberg mountain & into the legendary chimney. This is the only way to access the mountain top, and it is on race director Ryan Green's farm, so the Ossewa is a unique opportunity to experience this magnificent mountaintop trail run.

It's a slow climb through the chimney crack, which builds a sense of excitement as you weave through huge boulders and sprawling wild olive trees. The exit, high up top, left me breathless — not just my sea-level lungs adjusting to 2000m elevation, but a circling flock of Cape vultures directly above us was a welcome I'll never forget.

The views from up top were worth every minute of my journey from Cape Town and missing my Two Oceans blue number run. This was an adventure I never expected. The next two hours spent circling the flat-topped mountain on the smooth rock rim were a trail-running revelation. That this trail, probably first explored by San hunter-gatherers centuries ago, had only been discovered and opened to runners by the Greens in 2025, left me in awe once again of just how fortunate we are to live in an unspoiled country where time & space have literally stood still.

With the surrounding Drakensberg & Harrismith mountains providing a 360-degree horizon, and the Sterkfontein and race village dams shining down below, we trundled along at an unhurried pace, watching dogs & their relaxed owners swim in rock pools and take selfies. It's a long and steep enough route to tire experienced, fit runners, but just as doable for beginners who take all day & soak up fresh braai'd steak and cold beer at the happy-making drink stations.

A meandering descent into the vibey race village for a dam swim, long lunch and then sun-lounging on the grass or in tents to live local music is an idyllic way to unwind from a long run. Even the dogs were sufficiently stoked, lying among stroking strangers — another pleasurable aspect that I hope more races encourage.

After dinner, the booming big bonfires brought a warmth to the tented space and crowd, who danced or swayed away their lactic acid while hydrating with all sorts of dops to prep for day 2. After another misty, moody sunrise, we headed out onto another surprisingly scenic but refreshingly shorter & faster run. Lots of fun banter was shared by this unique mix of local farmers & city slickers, all soaking up the joys of a healthy weekend away from it all. This was ideal for an early lunch before the relaxed, deeply satisfied crowd headed home.