Founded by Toronto Argonaut quarterback John Henry Jackson, teammate Dave Mann, musician Archie Alleyne and restauranteur Howard Matthews, the Underground Railroad Restaurant fused soulful Black-American food, with music and history under one roof. The inside of the restaurant was decorated to share the history of the Underground Railroad, and the plight of Black enslaved people with write-ups and teachings of important historical Black figures during these times.

In 2021, the Underground Railroad Restaurant was honoured by the City of Toronto with two historical plaques, one for the original Bloor Street location and another for the King Street location. Their children were there to accept the honour and speak about their fathers' legacy. 

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Cosby Jackson is the son of John Henry Jackson, who was born in Columbus, Georgia in 1938 and came to play for the Toronto Argonauts in 1960. The idea for a restaurant with Black American soul food came from his, and Dave Mann’s longing for a flavour of home. 

Cosby describes the Underground Railroad Restaurant as a success from the start. “The city had seen nothing like it and it was a very exciting time. It was a very inclusive place, very welcoming to every race, creed and nationality. That was very important to my father. Politicians, celebrities and entertainers were all frequent visitors to the restaurant.”

Angela Mann, David Mann’s daughter, shares that there was some initial pushback from financial institutions, “I was aware that the financing of the restaurant was supported by the partners themselves, and a couple of Private investors/ friends, as they were consistently declined by financial institutions for loan support in their business”. Despite this, the restaurant opened and persevered. 

Angela tells us that her dad’s founding vision was “to share his life and all that is special and delicious in the Black experience of North America.” He hoped to educate and inspire others while honouring the 250 years of the underground railroad movement. 

The restaurant became a second home to Angela. “I spent much of my childhood there, it was a wonderful playing ground filled with love, family and an inspirational community, all smothered by a savoury aroma. I feel extremely fortunate to have been nurtured and shaped by this wonderful place in time.”

Tyyra Alleyne, is the eldest of Archie’s five daughters and also echoes the sentiment. “Walking into the restaurant, through the huge barn doors felt so extravagant. It was like walking back into history, seeing and learning about slavery through the decor and when seated, reading the placemats about Harriet Tubman and others that were on them. Dad used to let us go into the kitchen to see Sardinia and Charles who were the main chefs and see what they were cooking up. Then we got to get our own cornbread from the heated drawer which gave us pure joy.”

Howard, John, Archie and Dave were all friends. The bond between these four men was so close that Archie named Howard as Tyyra’s godfather and named John as his other daughter Tessama’s godfather.

Tyyra shares that on Sundays the Underground Railroad Restaurant held a story time and all the children of the owners would listen. “Sate Matthews, Tuku Matthews, Markus Matthews, Sarah Jackson, Cosby Jackson, Angela Mann, Melissa Mann and other children of the Underground family that worked there and outsiders would all be there listening to stories. 

“At that time in the 60's being so young, the food was a new experience for me as I never experienced southern food until the restaurant opened. It was definitely a long-lasting staple - even at home.” says Tyyra. “The Underground was a gathering place for many families of all races from all over the world. It brought people together to experience authentic Southern soul food. It was a local gathering for many people but also welcomed celebrities, such as Sidney Portier.”

Cosby recalls that in 1977 the year the Blue Jays became a team many players would make it a regular outing to bring their families and friends to the restaurant.

Angela too recalls the notoriety and impressive clientele. “The magic of the Underground Railroad Restaurant was its rising success, having stars such as Diana Ross, Mick Jagger, Robert Culp as loyal customers. This magic piqued the curiosity of all demographics. The Restaurant became a cultural landmark and a favourite place for countless people. The Underground Railroad Restaurant also brought an incredible sense of compassion within its walls, to those within communities who needed a safe place to be, a friend, or nourishment when working through challenging times.”

“My dad was a very engaging personality even though many people came to the restaurant obviously for the food, and the atmosphere they really came to see John Henry, Archie, Howard, and Dave. They were celebrities in their own right,” says Cosby. 

tUkU Matthews was quite young when the second Underground Railroad Restaurant location opened. She can still remember taking the Sherbourne bus to see the new and bigger restaurant location. 

An important part of the Underground Railroad Restaurant’s history to tUkU was the fact that it became an international destination spot. “When Black American folks would come to Canada, they would come to visit the restaurant as well. It was so well received in that way, which was a big deal because the food that they were preparing and presenting was from that Black food canon. Dishes consisted of ham hocks, chitlins, collard greens, candied yams and cornbread. This is very Black American legacy food that comes out of a lot of historical movements.”

tUku also points out that the Black Americans who took the trip to Toronto to experience this soul food may have felt an emotional tie to the voyage many took to hopefully find freedom in Canada, evoking parallels to the historic Underground Railroad route that Harriet Tubman took. “I would assume it mimics or touches on a memory around something that we survived.”

Tyyra says the restaurant helped her deal with the racism she was experiencing from the 60s to the 80s.”When the restaurant opened I was exposed to so many different people and I realized that not everyone was that way. There was such a diversity of people who came to the restaurant which showed me that not everyone is the same. My dad always said, ‘stand tall and be proud of who you are’. With the restaurant opening in the 60's by four Black men I soon realized that anything is possible.

tUkU shares that having the city acknowledge her family's legacy and both locations of the Underground Railroad Restaurant was a “profound” and “beautiful surprise”. 

tUkU also adds that she feels Toronto struggles to recognize and preserve important historical things. “Things grow, flourish, and then when they come to an end, they just literally disappear. And time goes by. And then all these generations have no clue that it took place.” The plaques ensure that the restaurant does not become another forgotten bit of the city’s history.

Cosby echoes tUkU on the importance of having the city’s recognition. “It’s obviously a big part of our identity as a family. Words cannot describe how proud I was for our families to have been honoured the way we were with the plaques. I just wish our dads could’ve been there. Still to this day people will tell me how much they missed the restaurant and the food. I do as well.”

“On numerous occasions, my friends would go, 'Oh my God, that's where my parents went for their first date' or ‘my parents love going there to eat’, says tUkU. “It was a place a lot of different Black communities participated in, and a lot of different ones because there are so many different Black communities in Toronto, right? There are so many ethnic groups considered Black people, which can be a very strange reality so it's nice to know that there was a place where people felt comfortable having an experience that was created for them.”