TrailFun Challenge : Fort Simon
Sat 24 Aug 2024 @ Stellenbosch Farms, Western Cape

Trail Fun

This run is so difficult it makes grown men cry -  one time even a Lady (unconfirmed)

If this is your First Time.

Welcome.  You need to do this run.  You need to show yourself that you can take on the impossible - and succeed.

This run is a metaphor for your life.  As you sit looking at this, it looks impossible and you think you will never be able to do this; you will never make it.  It's true, this is a challenge like no other.  We care about you and we want you to succeed.  We have a plan to help you overcome this impossible challenge.  There are simple steps you can follow that will help you achieve what you never thought you could.  We believe in you, we know you can.

When you get to the top of the hill (you will, we guarantee it) you will find the Mini Aid Station.  There are two things for you to stop, appreciate, and take in.  First, is your achievement.  You have made it and you will feel like you have never felt before.  On top of the world and able to take on anything life can throw at you  - and win!  The second thing you will notice, is the view.  If the first does not take your breath away, the second will.

Finish is at Fort Simon, in the shadow of the Castle.  Yes.  There is a castle and a fort and a bridge across a moat to get to the Tasting Room  Excellent food at reasonable prices.  you will be welcomed with a free wine tasting - you need to be rewarded and celebrate after what you have just achieved.  Fort Simon is the best place for celebrations (you'll see) 

Once you reach the finish, the first words out of you mouth will be that you never want to do this run again.  Its true, it takes its toll on you emotionally, the spiritual growth you experience requires a lot of energy.  It's hard and it's tiring. But we promise you this : the person that leaves the Start Line is gone - you are a different person when you reach the Finish.  You will never want to do this run again ... until next year.

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If this is your Second Time.

Welcome back.  This time will be different.

You may have convinced your mind that this was not too bad, but your body remembers.  We know you have goals, that you want to prove to yourself that last time wasn't a fluke - this is who you are; a person that can take on the impossible and arrive at the finish smiling (because you will be)

You are stronger now.  As you move up and down this route you will encourage the first timers, remembering your original struggles and how you thought you would never survive.  But you did, and your body remembers, and your mind remembers and your spirit pushes you forward; knowing that you can do this.  That is why you are here, that is what you want from this.

You will get to the Finish Line confident that you achieved what you wanted.  That you will never do this run again ... until next time.

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If this is your Third Time.

Please complete this quick Survey

  1. I am crazy.
  2. I run for the free drinks at the end.
  3. It was stay home or do this, so I'm here.
  4. If I run now, there is less chance of me killing someone later.
  5. There was a cute guy here last year; want to see if he's back.
  6. TrailFun has made me so used to hills, this is nothing now.
  7. I have become a medal collector.  You have a medal; I am at your run.
  8. We forgot this was the hard one.  Ag we're here, lets run it.

Can't lie to you, this one's not easy. If you hear Dirty Dancing in the background its because you're about to sign up for the Climb of Your Life.

If you normally run 10km, maybe do this 5km. If you think you can conquer the world then this 10km is for you. If you have done our TrailFun Series to this point then you are ready for this monster challenge. You can do this - we know!

Fort Simon has been renovated and it's looking spectacular. 

FREE GIFT to all runners, you can add a  bottle of wine by choosing that entry.  Don't miss out on the fun family vibe, excellent lucky draw prizes and your greatest running achievement of the TrailFun Series

Saturday 24 August 2024

Entries are from R70 to R270  There are  on the day entries at this event.

Do it today :

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Contact : Rodney Russell

Tel : 074 900 9235

Email : rodney[at]

Classes and pricing
Available classes for the event

Class Distance Start Time Price (pp)
TrailFun : 5km (Juniors) 5 km entry level 5km 07:00 R 70.00
TrailFun : 5km 5 km entry level 5km 07:00 R 170.00
TrailFun : 10km
Full 10km, no loop.
10 km 07:00 R 200.00
TrailFun : 15km 15 km run the 5km and 10km routes 07:00 R 200.00
TrailFun : 21km 21 km loop of the 10km route 07:00 R 200.00
TrailFun : 5km with wine
includes 3 x bottles of dry white wine (Chenin)
5 km 07:00 R 240.00
TrailFun : 10km with wine
includes 3 x bottles of dry white wine (Chenin)
10 km 07:00 R 270.00
TrailFun : 15km with wine
includes 3 x bottles of dry white wine (Chenin)
15 km run the 5km and 10km routes 07:00 R 270.00
TrailFun : 21km with wine
includes 3 x bottles of dry white wine (Chenin)
21 km loop of the 10km route 07:00 R 270.00

Event location
Fort Simon, Stellenbosch Farms

Coordinates -33.919507271942, 18.755393167114
Address Bottelary Rd, Stellenbosch Farms, Cape Town, 7600
City Stellenbosch Farms
Province Western Cape

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Registration Number: 2009/008890/23