Oakley House Winter Challenge logo header

Winter Challenge 2024

event fundraiser

A successful self-challenge and motivator to get us and our children off the couch and out into nature.

The Oakley House Winter Challenge fundraiser event aims to motivate through team accountability, ensuring that we remain active during the chilly winter months in Cape Town. This initiative holds significance for both our own well-being and that of our children, promoting good health and mental wellness. Stepping out into nature elevates our mood and cultivates a sense of achievement.

By taking part you are supporting the Oakley House Preparatory School in its annual fundraiser. Funds raised are, in part, used to supplement the many resources needed to facilitate specialised neurodivergent learning, ergonomic furniture for better posture and concentration, and we are able to continue subsidising school fees where necessary.

Challenge your friends and family to join us, your book club, your running or cycling groups, and your gym friends. Put it out there on your social media platforms as we would also like to raise awareness around the daily learning and behavioural challenges our children face, which are ongoing and overwhelming.

3 Categories to choose from

Expanding on the success of our previous Winter Challenges, we have created 3 categories to choose from catering to different comfort levels of all participants. How much do you want to challenge yourself and/or your team? You can have a maximum of 6 team members.

CASUAL – 1000kms over 4 months

CHALLENGE – 1500kms over 4 months

COMMITTED – 2000kms over 4 months

How this works

Challenge outline

  • Challenge starts on 1 June and ends on 30 September
  • Cover the distance chosen (1000, 1500 or 2000kms) over the 4 months
  • Walk or hike it, jog or run it, cycle or swim it ... includes treadmills, exercise bikes and gym pools
  • Challenge solo (you are the team, this is what you do) ... easy peasy as you train everyday anyway
  • Challenge in a team (max. 6 team members) ... easily affordable and doable
  • Challenge other teams ... other staff members, parents, learners, friends and family
  • Spread the news, creating awareness

Join the challenge

  • Once off entry fee of R1200
  • Solo entry ... you could ask family and friends to sponsor your efforts
  • Team entry (max. 6 team members) ... R200 per team member, that's less than two coffees per month – affordable yes!

Kids joining

  • Kids can join for free with no limit to how many join a team consisting of 6 adults
  • Create a family team and commit to moving in the afternoons and on weekends together
  • Older kids wanting to attempt the challenge in grade teams could be sponsored by family and friends


Tracking distances and progress

  • Starts 1 June
  • Be sure to track your distance in whatever way works for you ... you could use Strava, Fitbit, Garmin, etc.
  • Every Monday send your weekly kms to your team leader – they will remind you
  • Keep an eye out for the leaderboard on our social media platforms and in newsletters

Challenge events

  • Events will be organised to keep us motivated, get us together, and to keep us moving
  • Our launch event will be on Sunday 2 June, venue TBA
  • Closing event assemblies will be held early in the fourth term, dates TBA

Winter Challenge fun communications will happen via WhatApp messages, emails and social media posts, so keep checking. Any queries or troubleshooting can be emailed to .

Okay, I/we accept the challenge!


Choose your category. Decide if solo or in a team. Up to 6 per team (only one person to register a team).


Make a once off payment of R1200 via our QUICKET link ... includes EFT, Credit Cards and SnapScan.


Start moving and logging your kms from 1 June. Keep an eye out for the leaderboard at drop-off and pick-up.
Keep moving. Have fun!!

Put the challenge out there!

You have joined the challenge and we thank you!

... now challenge friends and family, clubs you might be a part of, other parents, Oakley staff, other grades.