TrailFun

07/09/2026

Want your day off to feel like a proper break?

It is easy for a public holiday to disappear into errands. Give yourself a morning of fresh air, good company and something to feel proud of.

At the TrailFun Heritage Day Run, we make getting outside simple: marked trails, on-route support and a pace that suits you. Join us at Simonsig on Thursday 24 September. Start with the easy, relatively flat 5km or choose a longer distance.

Walk or run, take home THE Socks and a huge metal butterfly medal, then enjoy your own afternoon braai plans.

Choose your distance and enter the Heritage Day Run:
https://entries.trailfun.co.za/events/83418-trailfun-holiday-series

06/09/2026

We promised a trail run. Some of you added a foot spa.

Thank you to everyone who joined us at Darling Cellars yesterday! Whether you splashed through the water or chose the bridge, ran for a time or walked with a friend, you helped make it a proper TrailFun morning.

And if this was your first time joining us, we hope you left thinking: “I can do this.”

There’s plenty more to look forward to. Here’s your next stretch of adventure:

Thursday 24 September
Heritage Day Run | Simonsig
A public holiday made for fresh air, amazing socks and a huge medal.

Saturday 3 October
Spring Series 3 of 4 | Delheim W**e Estate

Saturday 17 October
Thank You Run | Mitre’s Edge
Our extra thank-you event, with free entry for HERO members and runners who purchased a complete 2026 Summer, Autumn, Winter, Spring or Public Holiday Series.

Saturday 31 October
Stellenbosch Garden Town Run

Saturday 21 November
Spring Series 4 of 4 | Blaauwklippen W**e Estate

Saturday 5 December
DAM 360 | Arc of Franschhoek
A new adventure to look forward to!

Wednesday 16 December
Christmas at Vredenheim

Save these dates, send this to your trail buddy, and choose your next morning out.

Find upcoming events and available entries:
https://trailfun.co.za

You don’t have to be fast. You don’t have to run every hill. Come as you are. We’ll see you on the trails.

05/09/2026

03/09/2026

Route Marking Day at Darling Cellars.

We went looking for the hills today.

The 5 km appears to have misplaced them.

5 KM RUNNERS

This is one of the easiest and flattest TrailFun routes you could choose for your first trail run.

You will follow a simple 2.5 km out-and-back route. Run out to the mini aid station, turn around and follow the same route home.

There is one slight incline as you enter the owner’s farm.

That is about as dramatic as the climbing gets.

You will encounter the water twice. If you want the full Darling experience, head through it. If you prefer to keep your shoes dry, use the bridge.

Both choices are clearly marked. Wet feet are entirely optional.

10 KM RUNNERS

The 10 km is not much more intimidating.

You will share the gentle opening section before heading up into the vines, completing a loop around the vineyard block and returning to the main route.

There are a few gradual slopes, but nothing technical or severe. This is a route where you can settle into a rhythm and keep moving.

Take it gently and it is an approachable first 10 km.

Apply yourself and it becomes a fast, honest test.

15 KM RUNNERS

For the first time, Darling has one complete, continuous 15 km route.

You will continue all the way down towards the road, where the Minions will be waiting beside the route.

From there, you begin the zigzag journey back up, run parallel to the 10 km route and eventually join it for the return to Darling Cellars.

No completing 10 km, reaching the finish and having to convince yourself to leave again.

One start. One continuous route. One well-earned finish.

Today gave us dramatic clouds.

Saturday’s current forecast is giving us sunshine.

Your plan is simple:

1. Choose 5 km, 10 km or 15 km.
2. Choose The Race or the Relaxed Run.
3. Follow the flags and keep moving forward.

The route is marked.

The Minions are waiting.

Bull and Chicken are ready.

Now we just need you.

TrailFun at Darling Cellars
Saturday, 5 September 2026

Online entries close Friday at 18:30.

Enter here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

02/09/2026

At Darling, the finish line is not the signal to leave.

It is where the rest of your morning begins.

We have spent plenty of time telling you about the gentle routes, the canola, the railway line and that Bull-or-Chicken decision at the stream.

But perhaps the best reason to drive to Darling is what happens after you finish.

Darling Cellars has a huge grassy area with shaded picnic tables and benches where you can settle in after your run.

The restaurant will have breakfast options available for TrailFun runners, followed by its full menu of toasted sandwiches, pizzas and braai platters.

There will be w**e, local beers and other drinks available, as well as special offers on Darling Cellars w**es for the day.

And the weather currently looks almost unfairly good: a cool, sunny start followed by a pleasantly warm morning—perfect for finding a table outside and staying longer than you planned.

Darling may feel far away because it is a road you do not travel very often.

But for many runners coming from Durbanville, the drive to Darling takes roughly the same 40 minutes as the drive to Stellenbosch.

It is not necessarily farther.

It is simply in a different direction.

Your Saturday plan:

1. Choose the 5 km, 10 km or new continuous 15 km.
2. Follow the flags and finish at your own pace.
3. Find a table, order something good and let the morning continue.

We will give you the run.

Darling Cellars will give you a reason not to rush home.

TrailFun at Darling Cellars
Saturday, 5 September 2026

If you have been waiting to decide, now is the time:

https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

Online entries close Friday at 18:30.

01/09/2026

Darling is not the most convenient place to run this Saturday.

That is rather the point.

You could run five kilometres around your neighbourhood.

You could choose somewhere closer, finish quickly and be back home before the morning has really begun.

That would be easier.

But perhaps you do not need another convenient Saturday.

Perhaps you need to leave the usual roads behind, drive through canola country and spend a morning somewhere that feels different.

At Darling Cellars, you can choose an approachable 5 km, a runnable 10 km or our new continuous 15 km route.

You can race for a time or join the Relaxed Run and move at your own pace.

We will take care of the unfamiliar parts:

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

Along the way, you will run beside the canola field, follow the railway line and eventually decide whether you are feeling more Bull or Chicken when you reach the stream.

Then you will return to Darling Cellars for your medal, w**e tasting and the satisfaction of having done something more memorable than another ordinary Saturday run.

Darling may be farther away.

But sometimes you have to travel a little farther to feel as though you have actually gone somewhere.

TrailFun at Darling Cellars
Saturday, 5 September 2026

If this Saturday needs to feel different, you can enter here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

30/08/2026

Where to next?

Not necessarily farther.

Not necessarily faster.

Just forward.

Perhaps you have been thinking about trying your first trail run.

Perhaps you have been away for a while and need a reason to begin again.

Or perhaps you are ready to make the move from 10 kilometres to something longer.

You do not have to plan your entire spring today.

You only need to choose your next step.

Up next is Darling Cellars on Saturday, 5 September.

The Darling routes are gentle, open and runnable, with options for beginners, walkers and experienced runners:

5 km for an approachable morning on the trail.

10 km for runners wanting to settle into a comfortable rhythm.

A new continuous 15 km route for those ready to go farther without returning to the start after 10 kilometres.

We will make the unfamiliar part easier:

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

Along the way, you will run through the Darling countryside, pass beside the yellow canola field and eventually face one memorable decision at the stream:

Bull or Chicken?

Then it is back to Darling Cellars for your medal, w**e tasting and the satisfaction of knowing that you did something different with your Saturday morning.

You do not have to become brave all at once.

You just need somewhere to begin.

TrailFun at Darling Cellars
Saturday, 5 September 2026

When you’re ready, your next step starts here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

28/08/2026

The only difference between a Darling regular and a first-timer is one Saturday morning.

Every familiar face at TrailFun was new once.

They once sat in the car wondering whether everyone else would be fitter, faster or already part of a group.

They arrived without knowing the route, where to register or what would be waiting beyond the start.

Then someone smiled at them.

They chose their distance, followed the flags and discovered that they did not have to be fast to belong.

On Saturday, 5 September, some runners will return to Darling knowing all about the railway line, the stream and that inevitable Bull-or-Chicken decision.

Others will experience everything for the first time.

But everyone will follow the same flags, travel at their own pace and be welcomed across the same finish line.

If you are returning, help us make someone else’s first morning easier. Say hello. Share what you know. Remind them that walking is allowed.

If you are new, your plan is simple:

1. Choose your distance.
2. Choose The Race or the Relaxed Run.
3. Arrive exactly as you are.

We will mark the route. Our returning runners will bring the familiar faces.

You only need to take the first step.

Because after one Saturday morning at Darling, you won’t be the nervous first-timer anymore.

You’ll be one of the people who knows the way.

TrailFun at Darling Cellars
Saturday, 5 September 2026

When you’re ready to join us:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

Darling regulars, what would you tell someone joining us for the first time?

27/08/2026

Most runners think the important decision at Darling is whether to enter the 5 km or the 10 km.

It isn’t.

The decision that you may remember comes later.

Somewhere along the route, you will arrive at a stream and find two arrows waiting for you:

Bull or Chicken?

One choice takes you straight through the water.

The other keeps you out of the stream—but sends you up the embankment, across the railway bridge and down the other side.

Neither sign points towards the easy option.

And although you may already think you know which one you will choose, the decision feels slightly different when you are standing there with dry shoes.

Fortunately, you don’t have to decide today.

Your plan is simple:

1. Choose your distance.
2. Follow the flags.
3. Make your decision when you reach the stream.

We will show you both ways forward.

You decide what Becoming Brave looks like on the day.

Bull or Chicken?

Darling regulars, tell us which route you chose last time—and whether you would choose it again.

TrailFun at Darling Cellars
Saturday, 5 September 2026

If you would like to meet the Bull and Chicken for yourself, you can enter here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4

26/08/2026

Yesterday, we told you not to come to Darling for five kilometres.

So we made it fifteen.

For the first time in TrailFun Season Series history, Darling will have one complete 15 kilometre route.

Previously, our 15 km runners completed the 10 km route, returned to the start-finish area and then headed out again to complete the 5 km.

The hardest part was not necessarily running another five kilometres.

It was reaching the finish line—and choosing to leave it again.

So we have changed it.

This year, you will start once, follow one continuous 15 km route through the Darling countryside and return to the finish only when your full distance is complete.

No second start.

No passing the finish line at 10 km.

No asking tired legs to head out all over again.

This is a TrailFun first—and a new reason for our longer-distance runners to make the journey to Darling.

Your plan is simple:

1. Enter the 15 km.
2. Settle into your own rhythm.
3. Follow the flags all the way to one well-earned finish.

We will mark the route.

You bring the legs—and perhaps a little more bravery than usual.

TrailFun at Darling Cellars
Saturday, 5 September 2026

Enter the new 15 km route here:
https://entries.trailfun.co.za/events/84287-trailfun-spring-series-2-of-4