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Journey to Midnight: Rediscovering the Underground Railroad, Pt. I

In honor of Black History Month, we are exploring the complexity, bravery, and utmost historical significance of the Underground Railroad - especially within the scope of the Detroit region's unique role within its operation. Join us as we examine this great and tragic trail that forever redefined our region's history.

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Routes of the Underground Railroad leading to Detroit, codenamed "Midnight."

In the America of the 21st century, outdoor recreation - especially for expansive, extended periods of time - is largely regarded as a luxury.

Don't believe me? Take a quick look at your Instagram feed. If yours resembles anything like ours, then every couple of scrolls features a young-ish outdoor enthusiast living out their #VanLife, thru-hiking, or related outdoor-influencer lifestyle. Complete with pristine gear, jaw-dropping views, all smiles, and - inexplicably - zero sweat or dirt. Such public personas reflect the new "American Dream" for the "millennial" and "zoomer" generations: unending joy derived from carrying hardly any possessions, exploring beautifully planned and scenic trails, and freely hiking without any external pressures bearing down on you.

I wonder how glamorous this lifestyle would appear if we switched up a few variables.

How many thru-hikers would complete the Appalachian Trail if they could only hike at night - without any headlamps or trail signs? What would the completion percentage of the Continental Divide Trail reflect if hikers were unable to rest for 20 miles at a time? Would the Pacific Crest Trail retain its popularity if you could only begin the trail if carrying solely the clothes on your back?

Would anyone even attempt the North Country Trail - America's longest National Scenic Trail - if they knew, with absolute certainty, that they would be hunted for even attempting the feat?

These questions are obviously rhetorical. No one in their right mind would attempt to complete a journey under such harrowing conditions unless their life truly depended on it. America's outdoor culture would erode rapidly. Your TikTok feed would evaporate overnight.

Unless... unless such hikers had no other option than to set out on this apparent suicide mission. Unless the alternative of remaining in their current living conditions constituted a far, far worse existence.

Two centuries ago, hundreds of thousands of enslaved black men, women, and their families faced such a decision. They chose to potentially - no, likely - die in the pursuit of freedom vs. certainly die in the bondage of slavery. They chose to venture out into the darkness of the unknown, carrying nothing but a day's worth of food, their sweat-stained clothes, and an inextinguishable belief in their dignity as human beings.

These black Americans journeyed along the disparate and illicit trail system called the "Underground Railroad," traveling treacherously towards one final and almost mythical destination: Midnight.

The Underground Railroad (1893 ) by Charles T. Webber. Public domain image.


Let's start by knocking out one common misconception: the Underground Railroad was neither underground nor an actual railroad. Instead, the Underground Railroad grew organically from 1780 through 1861 as a series of interconnected trail networks united by one singular purpose: to guide escaped slaves from the southern United States towards obtaining freedom. This "railroad" consisted of several secret routes and safe houses scattered throughout the northernmost slaveholding states and extending all the way to the Canadian border. Alternative, shorter routes led south to Cuba or west to Mexico, although the vast majority of these routes led north.

The Underground Railroad derived its name from the terminology that "conductors" (the abolitionist network) and "passengers" (the escaped slaves) utilized to describe its network of "stations" (the safe houses). Passengers would travel from station to station following the "railway" - an indirect, inefficient, hazardous, and decentralized route intentionally maintained as such to avoid Federal bounty hunters. Even prominent conductors were unaware of the extent of the railroad in order to further protect both the fugitive slaves and the integrity of the routes, which often extended over 1,000 miles.

The clandestine nature of the Underground Railroad was brilliantly crafted and absolutely warranted. The success of the railroad in the early 19th century, with new routes opening regularly in tandem with northern states and territories electing to abolish slavery, prompted southern outrage and demand for Federal action. In 1850, Congress appeased the southern states by enacting a second Fugitive Slave Act, which included the following provisions related to convictions for harboring fugitive slaves anywhere within the United States:

  • Imprisonment and a fine of up to $1,000 (roughly $38,355 in today's USD) per fugitive.

  • Bonus compensation to judicial magistrates for successful convictions.

  • Bonus compensation to police officers that apprehended alleged runaway slaves.

  • Forced return of alleged fugitive slave to southern state of origin.

The passing of the Fugitive Slave Act of 1850 not only heightened the necessity of secrecy along the Underground Railroad, but also fundamentally changed its routing and composition. Most notably, the Act made Upper Canada (modern Ontario) - which had granted freedom to former American slaves since 1793 - the destination of choice for assured freedom.

The conductors wasted no time drawing up new routes to Ontario, including new stations that avoided well-traveled routes alone Lake Erie. New stations were established. And, due to relatively recent historical events, one state in particular became the most sought-after destination for the masses yearning for freedom.


Even in the 21st century, much of the Underground Railroad's history is simply unrecoverable. The requisite secrecy surrounding its entire operation means accepting the reality that we will never fully grasp the depth, nuance, and complexity that defined the long trail to freedom.

That being said, we in the Detroit region benefit from indisputable historical evidence that southeastern Michigan constituted a prominent route along the Underground Railroad towards southwestern Ontario. Beyond the geographic proximity of the two areas, abolitionist veterans of the War of 1812 recalled how easily the British-Canadian, American, and Native American armies crossed the Great Lakes during the northwest theater of the war. In fact, American prisoners of war were led on foot by their British captors across the frozen Detroit River to Amherstburg following the rout at the Battles of Frenchtown. .

There was just one catch, however: the Feds had just as sharp of a memory as the abolitionists. Bounty hunters during the antebellum era increasingly patrolled the port cities along Lake Erie, especially well-known gateway port cities like Cleveland. Crossing prolonged open water on the Great Lakes evolved into one of the riskiest segments of the entire Underground Railroad. Daring ships that carried fugitives, such as the Arrow, United States, Mayflower and Bay City, are known to us now only because they were caught in their daring mission.

With these Great Lakes risks steadily rising, the railroad rerouted its course northwest and over land, with most trails northbound converging upon Toledo, Ohio before diverting away from the lakeshore. The trail continued northwest in a seemingly counter-intuitive route, through Monroe County's sanctuary cities like Adrian and Tecumseh, until aligning with other eastbound routes in the capital of Michigan's anti-slavery movement: Ann Arbor.