The group are stopping at the North Yorkshire landmark as they retrace the journey of King Harold, they will travel from York to Battle in East Sussex where he fought William of Normandy.
Nigel Amos, who is leading the trek on behalf of the heritage charity English Heritage, said: "The legacy of the Norman Conquest is all around us, and for me this march is a great way of highlighting the enormity of what the people involved in the campaigns of 1066 undertook, as well as appreciating the richness of our country's heritage, from magnificent churches and castles to Roman roads and Saxon villages hiding in plain sight."
The journey will also take volunteers to Peterborough Cathedral, Bayham Abbey in East Sussex and Waltham Abbey, the place where - according to tradition - Harold was buried.
Emily Sewell, head of events for English Heritage, said: "Throughout 2016, English Heritage have been marking the anniversary of 1066 - one of the most famous battles and most transformative years in English history - at sites and events across the country.
"This march and our re-enactment weekend are the culmination of this year of activity and a great opportunity for people to find out more about these dramatic events."
The last Anglo-Saxon king of England, King Harold, travelled to Battle after defeating a Viking Army led by Harald Hardrada at the Battle of Stamford Bridge on September 25th 1066.
The English Heritage trek is due to be completed on October 14th, exactly 950 years since King Harold died fighting the Normans at the Battle of Hastings and the path was paved for William of Normandy to seize the throne.
Nigel Amos added: "I have been involved in re-enactment for many years and for me this is a once in a lifetime opportunity.
"We do as much as we can to research the details of the history we re-enact, but there's nothing like a personal experience like this to understand what it was like and offer an even more authentic window on that world to inspire and inform others."