One weekend might not be enough time to pack in 150 years worth of catching up.

Still, the Howard-Holland family will do their best.

Over the next three days, more than 200 descendants of fugitive slave Thomas John Holland will be reuniting in Hamilton — a new city for many of their American relatives, with a rich history for their bloodline.

Holland fled to Hamilton from Maryland in 1860. Here, he met Henrietta, the love of his life, raised nine children, and reportedly ran a hay and feed shop. Today, he and his wife share a tombstone that now sits in Hamilton Cemetery across the road from Dundurn Park, where the family will gather to picnic.

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Erasmus Toliver and his wife, Grace Holland - Thomas John Holland's daughter. (Courtesy the Holland family)

If the reunion-ers can find free time between a scheduled boat cruise, cook-out in Dundurn, night of dancing and Sunday morning church service, there are plenty of Holland-family landmarks to check out.

"The push has been for people to come here for the history," said Nerene Virgin, one of Holland’s great-granddaughters, and one of this year’s reunion coordinators.

She and her other local family members have offered guided tours throughout the city to showcase important locations in the Holland family story.

On their shortlist:

  • "Little Africa," an area on top of Hamilton Mountain where most slave fugitives, including Holland, first settled.
  • The former Hamilton Collegiate Institute, now the Central Memorial Recreation Centre, at Stinson St. and West Ave.South, which all of Holland’s nine children attended. (He and his wife didn’t want their kids to be illiterate like their father, so they "required" everyone to complete high school studies, Virgin said.)
  • The Stewart Memorial Church, where his son, John Christie Holland – who in 1953 became the first black man to be awarded Citizen of the Year – served as Pastor for many years, and where many black citizens gathered to discuss civil rights issues and seek refuge from aggressive Ku Klux Klan demonstrators in the 1920s.
  • The intersection of Mary St. and Wilson St. where Holland’s hay and feed store used to sit.
  • The former homes of Holland’s children.
  • The Hamilton and Woodland Cemeteries where Holland, his wife and children were buried.

Touring Hamilton streets through the Holland family experience, offers a glimpse into what life was like for black fugitive families in Canada.

It’s a history of tumultuous race relations countered by generous gestures; a struggle for resources and a testament to resilience, perseverance and family loyalty.

The Holland family’s success did not come easy. Touring the city only scratches the surface of where they’ve come.

Standing over his great-great-great grandfather’s tombstone the day before the reunion, Jackson Holland, 15, is aware of the struggles his family overcame and the sacrifices the first Holland made.

"I think if he could see our family reunion," the teen said, "I think he would be really proud — really happy that he did all of that, and it was all worth it."

For a virtual tour of black history in Hamilton through the Holland family, click on the pins on the map below.