The Witty family history came full circle five centuries later when their direct descendants, who had travelled from Canada, stood at the finishing post of England's oldest horse race on Thursday, part of a huge crowd celebrating the race's 500th anniversary in the Yorkshire Wolds.
The "Brigadoon of racing" - so-called in homage to the Scottish village which rises briefly out of the fog every 100 years - there was all of the old magic which draws regulars like racing historian Chris Pitt, who has not missed a race in 27 years.
Nearly 1,000 people assembled to see a record turnout of riders - 36 in all - and watch as Tracey Corrigan, from Sawdon near Scarborough, who said she had "just come for a jolly", triumph for a fourth time on her horse Frog.
Vanessa Witty, 23, from Edmonton, Alberta, had hoped to take part.
She said: "It's wonderful being here, and strangely nostalgic to walk around and know this is my ancestors' land."
Her direct ancestor Peter Witty, who died in 1534, was present with his brothers at the first race in 1519. And the brother of one of her ancestors Richard Witty, born 1802, won the race twice in the 1830s and 1850s.
Three friends from Melbourne were also among the international crowd gathering on the blustery course high in the Yorkshire Wolds.
Mr Pitt said: "Things like this are a dying breed and need to be preserved, whether it's horse racing or any age-old tradition.
"I love the atmosphere, the people. It's totally different to a regular race meeting.
"I have described it for years as the 'Brigadoon of racing' - you come here before 9am and it's a single track road, and by 1.30pm again it's a single track road.
"It is what happens in between that makes it so special on the third Thursday in March.
"It's four miles of grass verge, tarmac road, disused railway bridge and ploughed field and finishing on a grass verge after crossing the main Bridlington road."
Ms Corrigan, the second favourite, who won in 2014, 2015 and 2017, said it was her dream come true. The going was "fantastic" with no deep puddles to dodge.
The horse she was going to bring, a previous winner Bob Calapocus, broke its leg, and in the end she had to ride her horse Frog.
"I was going to sit at the back," she said. But once past the first crossroads she thought "go for it."
The 57-year-old added: "I am so proud, I didn't want to hurt me or the horse. I had two stumbles, quite a bad one on the side of the road, but he managed to stand up."
It was a momentous day also for Guy Stephenson, 86, who has been a trustee for more than 30 years, and whose father and brothers were past winners, who is now handing the reins to his daughter Clare Waring.
He was given a big round of applause during a special presentation for his longtime service to the race.
Mr Stephenson, who started helping out in 1956 when he got married and went to live at Nunburnholme Wold, and became a trustee in 1986, said: “I am just pleased that we got to 500 and hope that the people who are going to keep running it can keep running it for another 500 years.
“Things are getting difficult, it’s costing a lot of money to run, with all the health and safety.”
Fascinating facts about the race
No one ever knows quite who will take part - it could be anything from ex raechorses to riding cobs - until the day of the race.
There is no charge for spectators and no course as such. They run along a wide grass verge, sometimes a tarmac road. They cross two country lanes, one disused railway bridge and a main road.
The race is run according to 15 rules read aloud at the start by clerk Sue Hillaby - the fourth generation of her family to have held the post.
They include (number 6): "Every rider that layeth hold of any of the other riders or striketh any of them shall win no prize"
And most importantly (number 15) "Should the race not be run then it shall cease"
When it had to be abandoned last year due to dangerous conditions Stephen Crawford walked the course.
Racing was also cancelled during the foot and mouth outbreak in 2001 and in the winter of 1947.
Under the arcane rules the winner often gets less prize money than whoever is in second place.
Usually the winner gets £50 and a trophy and the runner up £4 for every horse that runs.
But this year entries went up to £5, Ms Corrigan won the £50, with Jason Carver who came second on Start Me Up, awarded £80.
The other £100 went to the Injured Jockeys Fund.