Bear Me Into Freedom

Scroll Down

Say the words “Talbot County,” and most people unfamiliar with the Eastern Shore of Maryland have no sense of where it is and what it looks like. Yet, without realizing it, millions of us share a common image of this rural tidewater area, one that comes from an improbable source.

You may recall the 2005 film Wedding Crashers, a raunchy, romantic comedy starring Owen Wilson, Vince Vaughn, Christopher Walken, and Jane Seymour, among others. It was staged primarily in Talbot County, including scenes shot in St. Michaels, one of the county’s small, gentrified waterfront towns. The St. Michaels portion features a lavish wedding at the Inn at Perry Cabin, an upscale resort on the town’s harbor. Played across the screen are frames of elegantly dressed women in pastel colors, men in tuxedos with crisp white shirts, champagne served on silver trays, tables piled high with gifts and hors d’oeuvres. It’s all lighthearted fun, frothy conversation, and general pleasantries against the backdrop of the resort’s tidewater buildings. 

Production Still From Wedding Crashers. Source: Alamy.

Not as well known is that nearly two hundred years earlier, a 15-year-old enslaved Black youth lived a few steps away from where that film was made, someone who became one of the most recognized figures in nineteenth century America. In 1833, the resort’s property was Perry Cabin Farm, and the main entrance of today’s resort contains the original farmhouse. This youth, who five years later would change his name to Frederick Douglass, recounted the “pitiless pinchings of hunger” that characterized his time on nearby Cherry Street in St. Michaels. As Douglass wrote in his autobiographies, he was “wretchedly starved” by his slaveholder, compelling him to be in constant search of food. There were no hors d’oeuvres for Frederick, just a thin allowance of corn meal once a week.

One source of sustenance would have been the water along the shoreline of Perry Cabin Farm with its abundance of fish, oysters, and crabs. There is no mention of Douglass taking advantage of this opportunity in his autobiographies, but in the early nineteenth century, the harbor would have been teeming with protein. Therefore, whenever I think of Wedding Crashers, I see a jarring image of a hungry Black teenager walking knee deep in the harbor, shoulders bent forward, eyes intently scanning the water, hands in it or holding some instrument to grasp what might be found, against the backdrop of the film’s richly dressed twenty first century White revelers oblivious to the sacred ground on which they stand.

During his enslavement in Talbot County, a place that is as much water as land, Douglass focused intently on using that water to shake off his bondage. The region’s maritime aspect has special significance in the life of Frederick Douglass because in the eleven years he lived in Talbot, he was never more than a few steps from the Chesapeake Bay and the rivers, creeks, and streams that fed it. Along the banks of those waterways were skiffs, canoes, and sailing craft, each a means of transport that would enable him to avoid roads and having to scurry past houses without being seen. For Douglass, these abundant watercourses were a pathway out of his oppression, describing “the waters of the Chesapeake” as “the highway from slavery to freedom.” Having ruled out any other way of escape from the narrow neck of land where he was bound, Douglass saw the water as giving him the best chance to rid himself of Talbot’s shackles.

The most memorable passage in his autobiographies, one that underscores the importance of the water to Douglass, comes from his time at Edward Covey’s farm where he had been leased as a field hand when he was sixteen years old. Located seven miles from St. Michaels on fields alongside the Chesapeake Bay, Douglass described how he would stand at the edge of that land looking across the Bay’s broad expanse and lament his fate, crying out to be released from the savage beatings he was being subjected to by Covey. Watching ships and sloops driven by their beautiful white sails on their way to distant places, he declared, “It cannot be that I shall live and die a slave. I will take to the water. This very bay shall yet bear me into freedom.” 

Bear me into freedom.

If there is one phrase that best characterizes Douglass’s experience in Talbot County, the plea he cried, the inspiration that drove him, it is—bear me into freedom. He had seen what it meant to be free during the part of his youth he spent in Fells Point along Baltimore’s harbor, working in its shipyards and walking about the city, and free is what he desperately wanted to be. 

When he was seventeen, Douglass’s carefully laid plans to seize a log canoe from a farm outside of St. Michaels and paddle up the Bay seventy miles towards Pennsylvania were discovered by his overlords. He was dragged off to jail in nearby Easton and then released to his slaveholder’s brother in Fells Point. But at least he was back where he had greater opportunities to realize his dream. 

What eventually did bear Douglass into freedom was not the water but rails. Masquerading as a sailor on leave from a ship plying the waters of the Chesapeake, Douglass boarded a train in Baltimore and stepped off another in New York. Still, he used his experiences along the waterways of Talbot County to formulate a narrative of his years here that have become among the most famous expositions of the evils of slavery and the imperative for bringing it to an end. 

Here is an excerpt from his autobiography, My Bondage and My Freedom, his lamentation while standing on the shore of the Chesapeake at the Covey farm. It is displayed in a font modeled after Douglass’s beautiful handwriting:

Let me be free! — Is there any God? Why am I a slave? I will run away. I will not stand it. Get caught, or get clear, I’ll try it. I had as well die with ague as the fever. I have only one life to lose. I had as well be killed running as die standing. Only think of it: one hundred miles straight north, and I am free! Try it? Yes! God helping me, I will. It cannot be that I shall live and die a slave. I will take to the water. This very bay shall yet bear me into freedom. The steamboats steered in a northeast course from North Point; I will do the same; and when I get to the head of the bay, I will turn my canoe adrift, and walk straight through Delaware into Pennsylvania. When I get there, I shall not be required to have a pass: I can travel without being disturbed. Let but the first opportunity offer, and, come what will, I am off. Meanwhile, I will try to bear up under the yoke. I am not the only slave in the world. Why should I fret? I can bear as much as any of them. Besides, I am but a boy yet, and all boys are bound to some one. It may be that my misery in slavery will only increase my happiness when I get free. There is a better day coming.

Jeff McGuiness
St. Michaels, MD
January 20, 2022

Stay Updated

Enter your email below for notifications to any additions to this website.

Share This Site

Please send this to others interested in life and works of Frederick Douglass