The Community Chest Unogwaja Challenge, is an incredibly special journey by bicycle that follows in the footsteps of the youngest winner of the Comrades Marathon, Phil Masterton-Smith – a man who very much epitomised the spirit of the Red Sock Friday or ShoOops! Movement.

Affectionately known as ‘Unogwaja’ or hare in Zulu, Masterton-Smith didn’t have train fare to get to Comrades back in 1933 and so cycled from Cape Town to Pietermaritzburg and then ran the Comrades Marathon and came 10th that year!

This example of ‘taking action’ to overcome one’s circumstances and follow one’s heart, is very much the backbone of today’s Challenge – a journey of hope and inspiration that has attracted people from all over South Africa and the world.

In 2020 we will host the 10th anniversary of the Challenge, which raises funds for educational and community development projects across South Africa.


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Our Beneficiaries

The Trust was founded to align the special message of Unogwaja with our collective charity vision and mission. This vision can be broadly described under “education” but at its core is the willingness to support, enable and empower those people in our country who have not given up hope and who are already doing their best to make it better for themselves and the people around them, regardless of their circumstances.

The Community Chest Unogwaja supports various projects across the country, which in the past has included Unogwaja Langa educational project, Vukasebenze Homeless Shelter in Cradock, Lebone Village and Umsilinga Primary.

Since 2011 we have raised in excess of R6-million.

The Challenge

This 1700km cycle from Cape Town to Pietermaritzburg to take part in the Comrades Marathon is a journey of the heart inspired by Phil Masterton-Smith (who’s nickname was “Unogwaja” meaning hare in Zulu). In 1933, Masterton-Smith lived in Cape Town and could not afford the train fare to Pietermaritzburg for the start of the Comrades Marathon. He got on his bike and he cycled there.

Today his courage and determination in the face of adversity are at the core of the Unogwaja Challenge which has become an annual journey that started in 2011 and brings together a small group of people chosen from all over the world for this special mission of hope across South Africa.

Applications for the 10th anniversary journey open on 1 August 2019. For more info email

Red Love Train

The Red Love Train is what we became known as during the Comrades “Up Run” 2013 which was one of the toughest races in living memory with one of the highest drop out rates in history due to fierce heat and head winds. The strength and the unity of the team, and the story and mission we are all brought together by, creates the opportunity to experience a truly unique Comrades journey that goes way beyond ourselves.

Whether you are vying for top honours or running your first Comrades and trying to make the 12hour cut off, if you feel passionately about being part of the Unogwaja mission, join us. You have an important role to play.

Unogwaja on Foot

On 1 May 2015 a journey on foot from Cape Town to Pietermaritzburg began in conjunction with the original bicycle journey inspired by Phil Masterton-Smith. The on-foot party left 30 days prior to the Comrades Marathon and the bicycle team left with 10 days to go. They met up the day before Comrades to enter Pietermaritzburg together.

Unogwaja represents a message of hope for everyone and we want everyone to be able to part of it be it cycling, on foot or just supporting the Light Fund.

This is the start of a long and important journey, that over time can bring together the whole nation. Something we can call our own, where we can stand next to each other and be proud of what we are trying to achieve.

A message from Unogwaja’s founder John McInroy:

Unogwaja is a growing legacy inspired by an incredible South African story of hope that we can all be part of. This is not an event; it is a team and movement you choose to step up for and offer yourself towards. Once you make that decision it is no longer you and us. It is WE. We will celebrate and face adversity together. The strength of this movement and the example we set, depends on your willingness to embrace this. And not just for the incredible, inspiring, grueling 11 day journey across South Africa. An Unogwaja is defined by his or her actions long after the cameras have been switched off and the dirt from your running shoes after Comrades has disappeared. That way we will ensure the legacy of Unogwaja, your legacy, will live on and hopefully continue to grow. Forever.

– John McInroy, Unogwaja Founder