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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.

The Middle Rouge River near Hines Drive was most likely a prominent route in the Underground Railroad


While we were researching this article, we stumbled upon two absolute truths. First, that the Detroit region provided an essential and pivotal final destination for the Underground Railroad. Second - and most frustratingly for an outdoorsman that loves retracing history - no one knows exactly where the main routes existed.

Similar to most historic Native American trails, the most prominent routes utilized by the Underground Railroad's conductors and passengers are still used today - but in a very, very different capacity. I-94 is the most prominent example of an Underground Railroad route that modern commuters traverse on a daily basis without thinking twice about the historical significance of their surroundings.

Despite the tragic paving-over of these historically and culturally-significant routes, our research efforts uncovered a variety of historical information pointing towards modern trails that were almost certainly used within the Underground Railroad. As mentioned, Ann Arbor's preeminent position as the abolitionist mecca of Michigan meant that virtually all Detroit-bound routes passed through the city. In modern times, Ann Arbor continues to lead the Detroit region as an innovator in creating outdoor recreation opportunities for its greater community, including the restoration, preservation, and creation of extensive trail routes. Furthermore, we know that rivers and other natural features were utilized as navigational directives, especially since most fugitive slaves were illiterate.

Armed with these data points, here are three modern trails that were most likely - if not certainly - a part of the Underground Railroad's vast network.

The Western Road: Dexter to Ann Arbor via the Border-to-Border Trail

Distance: 2.5 miles

Elevation Gain: 75 feet

Trail Orientation: Point-to-Point

Recommended Recreation Method: Running (trail and pavement), Cycling, or Kayaking

Aside from Midnight, Ann Arbor represented the principal destination of choice for freedom seekers passing through Michigan. Regardless of whether journeying north from Ohio or northeast from Indiana, all Detroit-bound railroad routes eventually converged in Ann Arbor. The efforts of prominent Ann Arbor residents like Guy Buckley, the editor of the anti-slavery newspaper The Signal of Liberty, nationally propagated the worst-kept secret about Ann Arbor providing a refuge for runaway slaves.

Just west of Ann Arbor, however, stood another recent settlement that provided a vital station for weary travelers along the desolate western Michigan segments of the railroad: Mill Creek Settlement, now known as the City of Dexter.

Thanks to historical, firsthand resources like an 1885 interview with Erastus Hussey of Battle Creek, Michigan, a conductor on the Underground Railroad, we know that Samuel Dexter - Dexter's namesake founder - was also an instrumental conductor along this "northern route" to Detroit. Dexter's prominent home called "Gordon Hall," located just northwest of the Village of Dexter, is also widely believed to have been a key Underground Railroad safe house within the settlement. Despite the inherent lack of certainty that surrounds most Underground Railroad research, available records definitely prove that Samuel Dexter assisted with the railroad's operation in and around Dexter, that a prominent railroad route led from Dexter to Ann Arbor, and that fugitive slaves often utilized rudimentary navigational directives like the Huron River for guidance.

As a net result of aggregating these historical data points, we can confidently state that the modern Border-to-Border ("B2B") Trail across Washtenaw County most likely traces the exact routes utilized for the railroad's Ann Arbor-centric segments. Of the B2B's established trails (several segments are still under construction), the Dexter-Huron Metropark segment leading from Downtown Dexter towards Ann Arbor follows the historical route that fugitives almost certainly traversed under moonlit and hushed conditions. The paved trail is best traversed on foot or by bike peddle, but paddling this route also comes with an added element of adventure - especially since voyagers along the Underground Railroad may also have completed this segment utilizing maritime transportation methods.

The Eastern Road: Ann Arbor to Ypsilanti via the Ann Arbor Ramble Trail

Distance: 5.9 miles

Elevation Gain: 42 feet

Trail Orientation: Loop

Recommended Recreation Method: Running (pavement), Cycling, or Kayaking

From the abolitionist stronghold of Ann Arbor, there were two primary routes to Midnight that passengers could follow. The more prominent - and therefore more dangerous - route continued down the banks of the Huron River towards another well-regarded Underground Railroad station: Ypsilanti, Michigan.

Similar to Ann Arbor and Dexter, some of Yspilanti's leading public citizens also held instrumental roles in the operation of the Underground Railroad. Ypsilanti resident George McCoy transported fugitives in wagons with false bottoms and gave them shelter in his barn, while Helen McAndrew hid passengers in either her octagon house or barn. Leonard Chase, “who resided on Cross Street at the summit of the hill,” ran a regular station there, and carried food to the hiding places of the near-starving men, women and children. These are just a handful of several brave Ypsilanti founding citizens - both white and black alike - that risked their lives and livelihoods to facilitate this immensely important station on the trail to Midnight.

The Ann Arbor Ramble trail displayed above also constitutes a segment of the B2B Trail, although this portion hugs the Huron River within a more urban setting. As such, while trail cyclists and walkers will lose somewhat of the isolation founder within Dexter-Huron Metropark, the constant presence of a large, surrounding community will hopefully instill an appreciation for the risk that fugitives bore while traversing the same route 200 years ago. Yes, abolitionist safe houses fortunately dotted the banks of the Huron along this route, but the homes and developments that you will jog, cycle, or hike past were likely standing in some earlier iteration during the antebellum era - and not all of those homesteads were friends of the abolitionist cause.

Nonetheless, thousands of indescribably brave conductors and passengers completed this nearly 6 mile passage from Ann Arbor to Ypsilanti in the most rudimentary and secretive of conditions. Today, you can retrace their steps along the immaculate B2B Trail's Ann Arbor Ramble section as a convenient loop, including multiple scenic crossings of the Huron River at Gallop Park. We also could not more strongly recommend paddling this pristine segment of the Huron River National Water Trail.

The Great River: Plymouth to Dearborn via the Hines Drive Ramble Trail

Distance: 15.1 miles

Elevation Gain: 229 feet

Trail Orientation Method: Point-to-Point

Recommended Recreation: Cycling to cover whole trail point-to-point; Running (pavement) also feasible for conditioned distance runners

The northeastern route of the Underground Railroad roughly followed the course of today's M-14 - a direct shot across the rolling hills of eastern Washtenaw County towards western Wayne County. After Ann Arbor, Plymouth provided the next abolitionist stronghold for fugitive passengers journeying slightly north towards the Detroit River. Beyond the litany of Plymouth homes and businesses that operated as safe houses, Plymouth's rise in prominence as a railroad station also resulted from another natural attribute: its location at the source of the Middle Rouge River, the meandering central vein of the entire Detroit region.

Nowadays, the route utilized by the Underground Railroad has largely been preserved within the Hines Drive Ramble trail. Just like the natural navigational directions received by the fugitive slaves, this trail follows the course of the Middle Rouge River from its official start in Plymouth Township to its embedment within the primary Rouge River in Dearborn Heights. Several locations along the Hines Drive Ramble were known or rumored to be Underground Railroad safe houses, including several homes, Mead's Mill, and most famously Nankin Mills.

The Hines Drive of 2023 provides a community staple for accessible recreation: paved trails, cleared brush, frequent outdoor events, sports fields, and engaging activity centers dotting the trailhead. Perfect for cycling and road running. However, for our more intrepid readers, we recommend that you lace up your hiking boots (or snow shoes) and follow the labyrinth of natural trails that intersect the main paved trail. These natural trails tend to more truly follow the route of the Middle Rouge, thereby increasing the likelihood of their use by freedom seekers two centuries ago. The light amount of maintenance allocated to these trails also preserves their inherent and somewhat unforgiving natural qualities - the perfect conditions for transporting back in time despite hiking through the heart of the developed Detroit region.


If you're still reading, thank you - this first part of our two-part series on the Underground Railroad covered a lot of ground (please forgive the pun) concerning the railroad's immense historical background, the Detroit region's significant role in the railroad's development, and the modern routes that sustain the legacy of the brave souls that traversed our familiar trails centuries earlier in the name of freedom. This is a heavy topic, and we sincerely hope that this lengthy article has provided some value to your understanding of the wealth of history and sacrifice that defines our beloved outdoors.

Part II of this series will zero in on the last stop on the Underground Railroad: station Midnight, aka the City of Detroit, and the conductors that facilitated the railroad's final passage across the Detroit River.

We'll see you at Midnight.

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