Capping off a year of painful social awakening, John Shackelford, a New York City bike messenger, rode 1,100 miles to retrace the Underground Railroad.

On the heels of a tumultuous summer last year, then-25-year-old John Shackelford embarked on an adventure cycling route from Mobile, Ala., to Washington, D.C.

Why adventure cycling? Because as he noted, it lacks representation among people of color. Why Mobile to D.C.? Because it retraces “where black people have come from (freedom from slavery) to where black people are today.”

And why set out at all? Well, to see — firsthand — just how far this country has come in the last 250 years.

Shackelford’s ride wasn’t just a personal quest. His mission became the focus of a new documentary: “Underground Railroad Ride.”

After the ride wrapped in October, Shackelford spoke with us about what he saw, what he learned, how cycling changed him, and — after seeing it all firsthand — how far we’ve really come.

This episode is sponsored by Polar. Find out more about their heart rate monitors & fitness trackers here.