In embarking on a 3,500-kilometre bike ride to follow the length of the Underground Railroad from New Orleans to Owen Sound, Ont., Alyssa Cudmore was hoping to meet some people, tell some stories on a blog, and learn more about the flight of slaves to freedom that had fascinated the 27-year-old since she was a child in Oregon.

Alyssa Cudmore

The 27-year-old from Dallas, Oregon, is travelling from New Orleans to Owen Sound, Ont., and eventually Ann Arbor, Michigan, by bike to honor the Underground Railway.

Then she felt the cold steel of a shackle around her neck, looked inside corner store trap doors to find tunnels that once led escaping slaves to sanctuary, read and took notes of the words slaves had used 160 years ago to describe their joy upon reaching freedom in Canada.

"It was almost impossible not to see myself as a freedom seeker out here as well," said Cudmore, who quit her job with a civil rights group before setting out from New Orleans on April 14. "Bouncing from one home to the next, never knowing what the next night will bring, who you will meet, who will be someone you can trust.  I have all of these bits of paper in my pockets with names of people, addresses, landmarks, safe places to go — my own 21st century Freedom Quilt.  

"And that was the beauty of the Underground Railroad.  You had to have faith that you would make it, that it would work out." 

She did have that same, “Man, I had made it” feel coming across the Canadian border in Fort Erie, but there is no way she can compare her experience on a bike burdened with 40 kilograms of comforting supplies with the burdens of a slave like Josiah Henson, who once wrote, “When my feet first touched the Canada shore, I threw myself on the ground, rolled in the sand, seized handfuls of it and kissed them and danced around till in the eyes of several who were present, I passed for a madman.”

Uplifting experiences

Cudmore has seen examples of lingering prejudice and inequality on her travels north, but she has been more buoyed by the goodness of the human spirit, and has witnessed how people of all creeds and colour can work together when faced with the obstacles of life.

A map of the railroad

The trail of the underground railroad spans all the way to northern Ontario. (Bing)

In Jefferson, Alabama, she found a community that had been divided —one side for blacks, the other for whites— until a week before she arrived on her sturdy bike.

"They had just got this new fire marshal in town, the first time they'd have an interracial volunteer fire department, so they decided to have a big community potluck, inviting the black community," Cudmore told CBC news. "It went off just fabulously, 300 people, it was a beautiful thing. I heard about the potluck from 10 different people in 24 hours.

"It was so cool. To most observers it would be archaic — it just shows how long things like that take." 

Part of her goal was to learn about the people along the route, and convey their stories on her blog, but she also learned about communities through their museums, including the first Underground Railroad museum — not the Oprah-inspired one — but one in the heart of the battles between slaves and abolitionists. 

"It's in a house once owned by a woman who had slaves, and then decided to become an abolitionist," said Cudmore, about a museum in Maysville, Kentucky, now run by a 91-year-old black woman and her son and daughter "The son brought me downstairs, where [the slave owners] used to keep their slaves in shackles. He put one of shackles on me and I can’t tell you how crazy impactful that was.

"I didn’t realize how much it would affect me until afterwards."

The Canadian pioneers

Cudmore knew about famed Underground Railroad conductress Harriet Tubman before riding her bike through Tubman’s terminus in St. Catharines on Sunday, but she was surprised to hear so much about Chloe Cooley, a woman from nearby Queenston who was being sold to Americans that prompted then-lieutenant governor John Graves Simcoe to act on the issue.  

Trap door to escape

A grocery store clerk shows Cudmore the trap door to the underground tunnel which led escaping slaves underneath the town of Mount Vernon, Ohio, and eventually to a home, now falling apart, where slaves escaped from.

"She was one of the catalysts that led to the 1793 Act to limit slavery in Upper Canada," said Cudmore, who has learned more about Cooley in conversations than in Canadian museums. Canada eventually abolished slavery in 1833.

Some of the early activists in freeing slaves were from Owen Sound — where she arrived today after 52 days on the road — but that is not Cudmore’s final destination. She will follow the route out of Canada through Detroit, where many slaves also crossed, and eventually get off her bike in Ann Arbor, Michigan, where she plans to start grad school in the fall.

A further 500 kilometres, which will make it a 4,000 km trip, doesn’t intimidate her.

She hopes to raise money for the museum in Maysville, but she also has some thinking to do.

"I could write a book on just the generosity of everyone I've encountered," said Cudmore, who has been fed, housed and given the comforts of home by strangers she has met on the way. "This generosity spans all bounds: religious, economic, racial, cultural, linguistic.

"I'm still trying to find a way to show my gratitude."