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The Underground Railroad Ride: Activism and adventure by bike

Five riders and a film crew hope to use history and the present to inspire a future generation of cyclists with the Underground Railroad Ride.

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Like many great bikepacking trips, this one begins with bike assembly and gear explosion on the cement sidewalk outside of an airport.

Yet, most of what follows will likely be unprecedented. On Friday evening, John “Bobby” Shackelford, a former bike messenger from Washington DC, and four of his cycling friends will ride away from the airport in Mobile, Alabama on a 1,114-mile journey that they hope is both equally history-telling and history-making

This bikepacking trip is called the Underground Railroad Ride.

Shackelford has been on plenty of bike tours before, riding from DC to Boston and even Latvia to Estonia, but after realizing that the documentation of adventure cycling through short films and media didn’t inspire him, he decided that his next trip would be more than just a bike ride.

“I couldn’t really relate to any of the adventure cycling videos I found online,” he told me. “They weren’t inspiring and they didn’t relate to me.”

The experience was revelatory: Shackelford decided that if he wasn’t inspired, then others probably weren’t either. He wanted to document a bikepacking trip in a way that was educational, exciting, and inspirational — especially to an audience that would normally glaze over during a bikepacking film. Once he decided on where he wanted to ride, some people were already hooked.

As Shackelford and his friends make their way from Mobile to Washington D.C. on the Underground Railroad Ride, a small film crew led by Jon Lynn will follow them. Faith Briggs, the impact producer for the project said that Shackelford and his friends “were going to go whether it was them with their GoPro’s or with a film crew.”

Nevertheless, in the Underground Railroad Ride, Briggs and the rest of the crew saw an opportunity to tell a story that went beyond the adventure of a bikepacking trip.

“In a year like this, when we’re really talking about what is the Black experience in America in a widespread way . . . in every place that this conversation is possible, we have to be having it,” she said. “For the riders, it’s through cycling, and for the filmmakers, it’s through our filmmaking.”

Much like the Underground Railroad of the mid-19th century, Shackelford’s route isn’t tethered to a specific line on a map. He chose the points between Mobile and D.C. based on landmarks that were used as designated safe havens or places for safe passage — and also where the riders and film crew had friends and family who could serve as historians.

“I’ve met people who think that the Underground Railroad is literally a railroad,” Shackelford said. “I’ve been baffled by that. If I can teach people some history, I wanna do it.”

The history lessons of the Underground Railroad Ride are also meant to challenge the realities of the present.

How has life changed for Black Americans in the places along the route? What did freedom mean then, and what does it mean now? How easy, or difficult, is it to freely move through some of the most bloodstained places in the United States?

Shackelford’s personal touring bike.

Shackelford and his crew are prepared to make people feel uncomfortable with what they find.

However, there’s yet another angle to the story: the pure adventure of a bikepacking trip.

Shackelford has been friends with his riding companions for years, all of them met through cyclocross or the bike messenger scene. Whatever they encounter along the way, they’ll do it together, and Briggs says that’s another important message that the film crew wants to communicate.

“So often our stories are contextualized in something that had to do with racism or the deficit statistics that we live in,” she said. “It’s a really wonderful opportunity to show some beautiful friendships between these guys. It’s gonna be fun. It’s gonna be joyous. It’s gonna be an adventure. It’s a story of friendships.”

Shackelford estimates that the adventure will take about 11 days. A handful of cycling industry brands have stepped up to donate gear or cash, and there is a GoFundMe account to help raise funds for the filmmaking.

For now, Shackelford is just ready to ride. And, as comfortable as he is on a bike, he’s much less used to being the center of attention. Nevertheless, as a film crew follows him around for the next 1,114 miles, he’s prepared to get used to the attention. After all, he wants to create the very thing that eluded him when he was looking for an inspirational adventure film.

“I’m not really outgoing,” he said, “but I felt like I could make a small change that also felt like it could be a big change to a lot of people. I hope they can be moved by it, and I hope they can relate.”

Follow along @theundergroundrailroadride

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