TrailFun

Darling is one of our easiest routes.

So naturally, we made the stream crossing unnecessarily complicated.

Both the 5 km and 10 km routes eventually reach a decision:

Bull or Chicken?

The Bull Route takes you straight through the water.

The Chicken Route avoids the water—but sends you up an embankment, across the railway bridge and down the other side.

So the Bull Route is wetter.

The Chicken Route is harder.

We may have named these badly.

The important thing is that neither choice is wrong. Both options are clearly marked, both return you to the same trail and both become part of your Darling story.

If you are new to trail running, the rest of the route is unusually gentle and runnable. You can race it, jog it or walk it. Your speed does not decide whether you belong here.

You simply need to:

1. Choose your distance.
2. Choose The Race or the Relaxed Run.
3. Decide what bravery looks like when you reach the water.

Sometimes it means running straight through.

Sometimes it means taking the bridge.

If you are going to drive to Darling, you should at least come home with a story.

TrailFun at Darling Cellars
Saturday, 5 September 2026

When you’re ready, enter here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-1-of-4

Yesterday, you became a little braver.

Nobody had run a TrailFun route at Asara before. Every one of you arrived without knowing exactly what was waiting beyond the start.

You chose your distance.
You chose The Race or the Relaxed Run.
Then you followed the flags and kept moving forward.

That long climb asked for patience. The downhill asked you to trust your feet. And somewhere between the start and the finish, you proved to yourself that you could do something unfamiliar.

We marked the route—but you did the brave part.

Thank you for trusting us to guide you around this beautiful estate. Thank you for the laughter, the encouragement and the way you made every first-timer feel that they belonged.

Thank you to Asara Wine Estate for opening its farm to us, and to everyone who helped make our first TrailFun at Asara possible.

Becoming Brave does not happen all at once.

It happens one flag, one hill and one finish line at a time.

Our next opportunity to keep moving forward will be at Darling Cellars on Saturday, 5 September—with gentler hills, wide countryside and one very important decision:

Bull or Chicken? 🐂🐔

Enter here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-1-of-4

Most trail runs finish in a parking lot.

Asara is a 5 star Hotel.

This one finishes on the lawn outside a five-star ballroom.

On Saturday, TrailFun comes to Asara Wine Estate: vineyards, wide-open views, a proper trail route, and a finish area that feels less like “right, where did I park?” and a little more like you have given yourself a morning out.

Our start, finish and prize giving will be on the grass in front of the ballroom. Afterwards, take a breath, collect your medal, enjoy the view—and stay a little longer if you can.

Asara’s hotel will be serving a full breakfast from 7:00 a.m., so whether you run 5 km, 10 km, walk the hills, chase a time, or simply come for a beautiful morning with your people, there is no need to rush away.

The route may make you work a little on the way up.

But Asara knows how to look after you at the end.

📍 Asara Wine Estate
📅 Saturday, 22 August
🏃 5 km and 10 km
⏱️ Relaxed Run: Start anytime from 7:00–9:00
🏁 The Race: 10 km at 7:40 | 5 km at 8:00

Enter now and discover it with us:

https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

Come for the run. Stay for the experience.

We had a choice at Asara: an easy first kilometre or a downhill finish.

We chose the downhill finish.

Today is route-marking day, and we are preparing every turn, split and climb for Saturday’s TrailFun at Asara Wine Estate.

The route begins with a gradual 2.5 km climb to the top of the farm. It gains roughly 100 metres—not steep, but steady. Take your time, walk when you need to, and trust the route. Once you reach the top, it begins to pay you back.

🌱 **If you’re doing the 5 km**

This route is absolutely manageable for beginners. Don’t try to prove anything on the opening climb. Settle in, run-walk if you need to, and keep moving forward.

Once you turn at the top, you have a beautiful downhill, spectacular views and a straightforward run back to the finish on the lawn outside Asara’s ballroom.

⛰️ **If you’re moving from 5 km to 10 km**

You’ll follow the same opening climb and fast descent, reaching the water table just after 4 km.

At the route split, the 5 km continues straight while you turn left for the lower-farm loop. You’ll descend to the bottom of the farm before gradually zigzagging your way back up.

Keep your effort sensible, use short walk breaks if you need them, and save something for that final downhill to the footbridge and finish.

🏃 **If you’re a seasoned runner**

This is a runnable, non-technical route. The opening climb is your main opportunity to settle into a strong rhythm. After that, let the descents flow, enjoy the smaller rises—and remember to look up. The Asara views are worth it.

You don’t need to know the farm.

You don’t need to worry about which way to turn.

We will mark the route. Your job is simply to keep moving forward.

Entries close tomorrow at 18:30.

Don’t spend Saturday morning wondering whether you should have joined us. Enter now and meet us at Asara on Saturday.

📍 Asara Wine Estate
📅 Saturday, 22 August
🏃 5 km and 10 km
⏱️ Relaxed Run: Start anytime from 7:00–9:00
🏁 The Race: 10 km at 7:40 | 5 km at 8:00

Enter now and discover it with us:

https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

The route is new.

The way we look after you isn’t.

Going somewhere unfamiliar should feel exciting. It shouldn’t leave you wondering whether you will know where to park, where to start or which way to turn.

At Asara, everyone will be a first-timer.

But nobody will be left to figure it out alone.

We have explored the farm, designed the routes and found the paths worth following.

On Saturday, you can expect the same TrailFun experience you already know:

🚩 Clearly marked routes
💧 A friendly aid station
⏱ Official timing
🏅 A medal at the finish
🌿 The freedom to race, run or walk
🦋 A place where you don’t have to prove that you belong

Your plan is simple:

1. Choose your distance.
2. Choose The Race or the Relaxed Run.
3. Follow the markers and keep moving forward.

📍 Asara Wine Estate, Polkadraai Road, Stellenbosch
📅 Saturday, 22 August
🏃 5km, 10km, 15km or 21km
⏰ Relaxed Run: start anytime from 7:00–9:00
🏁 The Race: 10km at 7:40 | 5km at 8:00

New farm. New route. Same TrailFun.

There will never be another first TrailFun at Asara.

Enter now and discover it with us:

https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

The peacock has already won.

Best outfit. Best entrance. Least concern about his finishing time.

So that takes some of the pressure off you.

Running has a strange habit of beginning as something we do to feel good—and slowly becoming another way to judge ourselves.

Pace. Position. Personal bests. Whether somebody on Strava ran the same route faster.

There is nothing wrong with wanting to run a good time. That is why TrailFun has The Race.

But sometimes your week doesn’t need another performance review.

Sometimes you simply need to have a good time.

That is why we also created the Relaxed Run.

At Asara, the choice is yours:

🏁 Run a good time
Join The Race: 10km at 7:40 or 5km at 8:00.

🌿 Have a good time
Start anytime between 7:00 and 9:00. Walk the hills, stop for the views and complete 5km, 10km, 15km or 21km at your own pace.

Both options follow the same marked routes. Both receive official timing and a medal. Both finish in the same friendly place.

Your plan is simple:

1. Choose the kind of good time you need.
2. Choose your distance.
3. Keep moving forward.

This Saturday, you can chase the clock—or forget about it completely.

📍 Asara Wine Estate, Stellenbosch
📅 Saturday, 22 August

Choose your good time:
https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

You’re going to feel lost here.

Not lost as in *we have no idea where you are*.

Lost as in *you have never seen this path before, and you don’t know what is waiting around the next corner*.

But here is the good news:

Nobody has done this TrailFun route before.

Not the regulars.
Not the racing snakes.
Not the walkers.

At Asara, everyone starts with exactly the same amount of experience: none.

So if you feel uncertain, you are not behind. You are standing in precisely the same place as everyone else.

That is where TrailFun becomes your guide.

We have explored the farm, planned the route and found the paths worth following. On Saturday, we will mark every turn and show you where to go.

Your plan is simple:

1. Choose your distance.
2. Choose The Race or the Relaxed Run.
3. Follow the markers and keep moving forward.

You don’t need to know the way.

We have designed this route for you.

📍 Asara Wine Estate
📅 Saturday, 22 August
🏃 5km, 10km, 15km or 21km
⏰ Relaxed Run: start anytime from 7:00–9:00
🏁 The Race: 10km at 7:40 | 5km at 8:00

Come somewhere you have never been before.

We’ll make sure the finish line is worth reaching.

Enter here:
https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

Where to next?

Sometimes bravery doesn’t look dramatic.

Sometimes it is simply choosing somewhere you have never been—and deciding to show up.

Next Saturday, TrailFun heads to Asara Wine Estate for the first time.

New places can give us butterflies. That physical buzz of nerves and excitement can feel remarkably similar: your heart beats faster, your energy rises and you start wondering what lies ahead.

Perhaps those butterflies aren’t telling you to stay home.

Perhaps they’re telling you that something new is about to begin.

At Asara, everyone will be a first-timer. You don’t need to know the farm or the route. We will mark the way.

Your job is simply to choose your distance, choose your start and keep moving forward.

📍 Asara Wine Estate, Polkadraai Road, Stellenbosch
📅 Saturday, 22 August
🏃 Walk or run 5km, 10km, 15km or 21km
⏰ Relaxed Run: start anytime from 7:00–9:00
🏁 The Race: 10km at 7:40 | 5km at 8:00

New farm. New route. Same TrailFun.

Entries: https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4

At Asara, everyone will be a first-timer.

We visited the farm today to explore the trails and begin putting together a brand-new TrailFun route.

We found vineyard roads with enormous views, quiet stretches beneath the trees, a little green single track—and even a few locals who appeared to be wearing considerably more impressive outfits than ours. (check out the last picture)

Nobody has run this TrailFun route before.

Not the regulars.
Not the racing snakes.
Not the walkers.
Not even us.

There is something exciting about standing at the beginning of a path and not yet knowing exactly what lies around the corner.

On Saturday, 22 August, we get to discover it together.

New farm. New route. Same TrailFun.

📍 Asara Wine Estate, Polkadraai Road, Stellenbosch
📅 Saturday, 22 August
🏃‍♀️ Walk or run 5km, 10km, 15km or 21km
⏰ Relaxed Run: start anytime from 7:00–9:00
🏁 The Race: 10km at 7:40 | 5km at 8:00

When you’re ready: https://entries.trailfun.co.za/events/84286-trailfun-spring-series-1-of-4