English Heritage has organised the trek on horseback and foot from York to East Sussex to mark the 950th anniversary of the famous clash.
The volunteers will arrive on the battlefield 950 years to the day since Harold fought William of Normandy.
Nigel Amos, leader of the march for English Heritage, said it was a "once-in-a-lifetime opportunity".
King Harold defeated a Viking army at the Battle of Stamford Bridge in East Yorkshire, on 25 September, 1066, before travelling south to face the Normans.
On 14 October, he fought and was killed at the Battle of Hastings.
William then seized the English throne.
Emily Sewell, head of events for English Heritage, said 1066 and the Battle of Hastings was "one of the most famous battles and most transformative years in English history".
Nigel Amos, who is leading the march on behalf of English Heritage, added: "There's nothing like a personal experience to understand what it was like and offer an even more authentic window on that world to inspire and inform others."

The Battle of Britain Memorial Flight's Lancaster, known as Thumper, based at RAF Coningsby, took the skies for a test flight on Monday.
The Lancaster, one of only two in the world able to fly, missed most of the 2015 display season.
Squadron Leader Martin Morris said a schedule for subsequent flights will be announced over the next few weeks.
Sqd Ldr Morris, who heads up the Battle of Britain Memorial Flight, said: "Spares and parts are difficult to find and some had to be manufactured.
"The aluminium for the bulkhead had to be sourced from the same type of aluminium as the original aircraft - so it has not been without challenge - but our engineers have succeeded."
Hundreds of people turned out to watch as Thumper took to the skies at about 14:00 BST.

Dr Kate Parkins said, in the last 18 months, another five children in Greater Manchester have also suffered life-changing injuries as a result.
She said the button-shaped batteries "look like sweets" to children but can cause severe internal bleeding which medics struggle to treat.
Lithium batteries are found in items such as toys, keys and smartphones.
Dr Parkins, a lead consultant for the region's Paediatric Intensive Care Transport Service, is calling for a national campaign to highlight the dangers.
"They look innocent enough and therefore nobody thinks to put them out of reach from children," she said.
One child died in May last year after a battery got lodged in the upper part of the feeding tube, she said.
"It had been removed and then, about a week later, caused catastrophic bleeding which we couldn't control."
The most serious cases are associated with Lithium button batteries larger than 20mm (the size of a 10 pence piece) which can cause severe injury within two hours.
And they do not have to be damaged, crushed or chewed to cause serious harm.
"It's not what's inside the battery," she explained. "The battery sets up an electrical current which causes a build-up of sodium hydroxide which is caustic soda.
"That causes a burn through the oesophagus, the feeding tube, and that can then burn through into major blood vessels and that's why the bleeding is then pretty much impossible to control and stop."
The consultant at Central Manchester University Hospital Trust also wants to raise medical awareness "because a lot of doctors are unaware that this can cause harm either".
Dr Parkins said in the second fatal case, medics did not know if the three-year-old had swallowed a button battery.
"She suffered catastrophic bleeding which again with all medical intervention we couldn't control.
"She died because of severe haemorrhaging, severe blood loss."
Children who have survived have been left with "severe life-changing injuries", she said.
"Two deaths is too many as far as we're concerned. Two or three patients having severe injuries is too many when it's something potentially preventable."
Central Manchester University Hospitals said the children treated after swallowing the batteries were aged between 12 months to six years old.
A group of "warriors" are staging a 300-mile march to echo King Harold's journey to the Battle of Hastings.
[NEXT_CONCEPT]
The last airworthy Lancaster bomber in Britain has flown for the first time since being grounded by a fire in May.
[NEXT_CONCEPT]
A leading paediatrician has warned of the dangers of lithium batteries after two children swallowed them and died.