More than 200 descendants of a fugitive slave will be reuniting in Hamilton this weekend. They return to the city where their family first gained freedom.

It was 1860 when Thomas John Holland escaped slavery in Maryland. He fled through the Underground Railroad which led him to Hamilton. For the first time his descendants will reunite in the city where he first lived as a free man.

"Our family has a rich, rich history in Hamilton," said Nerene Virgin, a great-granddaughter of Holland, and an organizer of the event. That they haven’t had a reunion here yet is "kind of surprising," she said.

Family members coming to Hamilton from all over the U.S.

A family of high-achievers, many of the Howard-Holland kin went on to make impressive careers for themselves across North America. Holland’s son, John Christie Holland, was named Hamilton’s Citizen of the Year in 1953 for his humanitarian contributions. He was the first black person honoured with that award.

This weekend many will be coming from Maryland, South Carolina, California and Ottawa to celebrate the three-day reunion. Among them: lawyers, professors, human rights activists, newspaper publishers, a development and diplomacy worker, a secondary school principal, a computer engineer, a television music composer and business owners. Success, it seems, is in the genes.

Virgin herself has been a teacher, a CBC television reporter and anchor, political candidate in the Hamilton Mountain riding, anti-racism activist, and may be best known as an actor — she played "Jodie" on TVOntario’s children’s program Today’s Special in the 1980s.

"The saying in our family was ‘you rise above,'" Virgin said. "And that came from what my great-grandfather did. It doesn’t matter what life hands you, you rise above it."

Escaped slavery at the age of 15

Thomas John Holland was only 15 when he made the dangerous two-month trip to seek refuge in Hamilton. He evaded bounty hunters chasing runaway slaves. He slept in swamps. He swam across the Niagara River and fended for his life in the wilderness, Virgin attests.

That's a lot for Virgin's grandson, Jackson Holland to live up to. He was born in Hamilton and is 15 years old — the same age his great-great-great-grandfather was when he ran for freedom. He hasn’t attended a reunion yet — most take place in Maryland — but he says he is excited to finally meet his extended family.

He knows his family is exceptional. He hasn’t heard of any other kids at his high school who have big reunions like this.

And when he reflects on his family’s particular accomplishments, he says he feels "very happy." That they could overcome adversity and racism. It fills the teen with confidence.

"I feel like if I ever have any obstacle in my way, I can defeat it," he said. "Because I know it’s in me, it’s in my blood."

The reunion will run from Friday to Sunday and will include a boat cruise, afternoon picnic at Dundurn Castle and Park, an evening of dancing and a church ceremony at the Stewart Memorial Church.

In Virgin’s opinion, the reunion is an opportunity for her American relatives to tour Hamilton and learn about their past. And for the younger members, like her grandson, it will be a chance to "rub shoulders" with a group as successful as them.