The 5 Black men who biked 1,100 miles on the Underground Railroad to honor their ancestors

The Underground Railroad was a large movement in North America consisting of several individuals who worked together to aid enslaved men and women in their escape from their captors.

The freedom network began in the 1830s; there were homes, schoolhouses, churches and businesses which became known as “stations” along the route toward the north. These homes provided temporary shelter for fugitive slaves before they continued the rest of their journey.

The Underground Railroad extended to Canada in 1834 after the latter had outlawed slavery. By the end of 1850, the network had helped over 10,000 slaves escape to freedom.

In September 2020, five Black men decided to honor the spirit of their ancestors by biking 1,100 miles along the Underground Railroad. Brooklyn native John Shackelford, who organized the trip from Washington, D.C. to Alabama, has biked all over the world, including Niagara Falls, Helsinki, and Riga. Now in his mid-20s, he said he was inspired to bike along the Underground Railroad after attending Black Lives Matter protests in 2020.

“That was my big message,” Shackelford told Bicycling. “To inspire more people like me to do what I love.”

While planning the trip, Shackelford said he thought of following an official Underground Railroad bike trail. However, after research, he realized that there were no prescribed routes at the time, so he decided, in the spirit of his ancestors, to make his own way.

Shackelford then recruited four of his closest friends for company and safety, according to Bicycling. His four friends were: Rashad Mahoney, 30, a bike mechanic; Edwardo Garabito, 28, a custom bike builder; Richard Carson, 28, a bike messenger and serious autocrosser; and Alexander Olbrich, 27, a sales manager.

The trip started in Mobile, Alabama on September 25 at Africatown, an early free Black settlement, and ended in Washington D.C., a city built by enslaved people and where Shackelford grew up.

Shackelford also backed a $100,000 fundraising effort, including merch sales and sponsorships, in support of a documentary project attached to the underground railroad bike ride. An 11-person film crew trailed in a 15-passenger van, with two more people in another van towing a trailer to provide road support.

Despite concerns about COVID and anti-Black racism, the ride was successful.

“Everyone else had some sort of long-distance experience under their belt,” Olbrich said.

“But I had never done anything like this,” Mahoney added. “We tried to have this ‘no man left behind’ thing early on.”

Bicycling reported that “most days began at 5 a.m. with a quick stretch and a big breakfast before the group ping-ponged from local interviews to museum tours to documentary shoots. Between detours, they’d actually put in the miles.”

The bikers said the riding itself was “soul-cleansing, full of rural scenery under sunny skies”. They sometimes received cheers from onlookers.

“When you have a solid crew like ours,” Shackelford said, “riding is more relaxing than a daunting task.”

The men told Bicycling that when their cycling GPS started going for more meandering routes, Google-mapped highway routes became their chief support.

After their two-week journey, the men made it into Washington, D.C., to the finish. Mahoney, who was moved by the Black Lives Matter painted in the streets and other images he saw posted on the fence, said he hopes their ride inspires would-be social justice warriors to “drop the virtue signaling and take to the streets.”