Douglass Returns


Approximate driving time is one hour

Douglass faced the worst depths of chattel slavery between 1834 and 1836 in the area west of St. Michaels known as Bayside or the Bay Hundred. Bayside farms were smaller than local plantations and were often occupied by tenant farmers using hired labor, both enslaved and free.

At about 8 years old, Douglass was dispatched to Baltimore and the Fells Point household of Hugh Auld, a ship carpenter. When Douglass was recalled to St. Michaels by Hugh Auld’s brother Thomas, he was 15, a fast-growing teenager. In urban Fells Point, he had the ability to fraternize with black and white friends, attend church, improve his reading, and move around the city when not at work in the shipyard.

In contrast, St. Michaels was a depressed, poor community with violent racism ingrained in local customs. In the fall of 1833, Douglass worked with several others in the community to start a Sabbath school for black students. Not only was the school broken up by a mob at its second meeting, it was also the last straw for Thomas Auld. Shortly after the school incident, Auld rented Douglass to Bayside farmer Edward Covey, infamous for his ability to break the spirits of rebellious slaves.

In the isolated Bayside, Douglass became a man and determined he would be free. This tour passes through St. Michaels, where Douglass lived in Thomas Auld’s household in 1833. From St. Michaels, the tour proceeds to Bayside. You can view the farms where Douglass was rented out for hard field labor beginning in 1834 and ending in 1836, when he was jailed in Easton for attempting to self-liberate using a Chesapeake Bay log canoe. You will see the open waters of the broad Chesapeake Bay that inspired him to seek freedom.

PLEASE NOTE: These tours will take you on busy roads, as well as many rural back roads. Use caution when pulling off to view a site or read from the guide. Many of the buildings associated with Frederick Douglass in Talbot County are no longer standing, and their exact locations are unknown; this guide directs you to the approximate vicinity of each site. In addition, many of the sites included are private property. Please respect property owners and do not trespass or use private lanes and driveways. In Talbot County, road names with green signs are public. Roads name with blue signs are strictly private.

Self-Guided Driving Tour #3

Site #1 — Frederick Douglass Historical Marker, St. Michaels, Talbot Street at Mill Street

Use the Mill Street lot to park and read the historical marker located in the small roadside park. Walk one block south to the southeast corner of Talbot and Cherry Streets to begin your tour.

Site #2 — Site of Thomas Auld’s Store and Post Office

Thomas Auld kept a store on this corner and lived in the block behind it, toward the harbor. The site is now a bakery. Auld scrambled to make ends meet. He rented the store and a contract to serve as postmaster helped maintain some year-round income. In 1833, Auld was married to his second wife, 22-year-old Rowena Hambleton, daughter of Bayside farmer William Hambleton. Rowena’s youth didn’t equip her to manage a household or act as stepmother to 12-year-old Amanda Auld, Douglass’s friend from their early childhood on the Lloyd planation. Rowena attempted to run her household through meanness and stinginess while Thomas Auld deployed the lash with an inconsistency that bred disrespect in his slaves. Hunger was ever-present Douglass wrote of “the brutalizing effects of slavery upon both slave and slaveholder”..

There were four slaves of us in the kitchen, and four whites in the great house — Thomas Auld, Mrs. Auld, Haddaway Auld, (brother of Thomas Auld,) and little Amanda. The names of the slaves in the kitchen, were Eliza, my sister; Priscilla, my aunt; Henny, my cousin; and myself. There were eight persons in the family. There was, each week, one half bushel of corn-meal brought from the mill; and in the kitchen, corn-meal was almost our exclusive food, for very little else was allowed us…This allowance was less than half the allowance of food on Lloyd’s plantation.

Douglass goes on to describe his strategy to find enough food: [He spelled Hambleton as Hamilton.]

One of my greatest faults, or offenses, was that of letting [Auld’s] horse get away, and go down to the farm belonging to his father-in-law. The animal had a liking for that farm, with which I fully sympathized. Whenever I let it out, it would go dashing down the road to Mr. Hamilton’s, as if going on a grand frolic. My horse gone, of course I must go after it. The explanation of our mutual attachment to the place is the same; the horse found there good pasturage, and I found there plenty of bread. Mr. Hamilton had his faults, but starving his slaves was not among them. He gave food, in abundance, and that, too, of an excellent quality. In Mr. Hamilton’s cook—Aunt Mary—I found a most generous and considerate friend. She never allowed me to go there without giving me bread enough to make good the deficiencies of a day or two. — Frederick Douglass, My Bondage and My Freedom

Unable to discipline Douglass, and always looking for money, Thomas Auld rented Frederick Douglass out for the year 1834 to the cruelest “slave breaker” in the Bayside neighborhood.

Return to the car and proceed to Site #3. You will now follow the route Douglass walked on the cold morning of January 1, 1834, the full seven miles to the rented farm of Edward Covey (pronounced KOH-vee).

In approximately three miles on the right, on the way to the Covey Farm, you will pass Emerson Point Road, the former lane gate of William Hambleton’s farm, where Douglass sent the Auld’s horse on “grand frolics” for food as described above. In 1836, Douglass would plan to steal a log canoe from this farm as a means of sailing up the Chesapeake to freedom.

In approximately five miles on the right, on the way to the Covey Farm, you will pass Wade’s Farm Lane, the former lane gate of the Hatton Farm. In 1834 it was part of Wade’s Point Farm, owned by descendants of clipper ship builder Thomas Kemp. Interestingly, both the Hatton Farm and Wade’s Point once belonged to the Aulds. (Thomas and Hugh were born here.) Also of note, the Hatton farm would later become the first large diversified farm to be owned by an African American in Talbot County.

From 1920 to 1925, African-American farmer Charles Caldwell, Sr. produced livestock, corn, wheat, tomatoes, and other vegetables here. His wife, Ethel Adams Caldwell, operated a bed-and-breakfast in the 13-room house. They next moved to across the road to Clay’s Neck, a 156-acre farm.

Charles Caldwell, Sr., was born in 1881 and could have met Douglass on his return trip to St. Michaels in 1893. The Caldwell family were among Frederick Douglass’s friends. In 1835, Douglass had worked with Handy Caldwell.

Of his return trip to Talbot County in 1877, Douglass writes in his book, Life and Times of Frederick Douglass, “It should in the first place be understood that I did not go to St. Michaels upon Capt. Auld’s invitation, but upon that of my colored friend, Charles Caldwell.” 

Site #3 — New St. Johns United Methodist Church — View of the Covey Farm

9123 Tilghman Island Rd, Wittman, MD 21676

From the church parking lot, you can see the fields of the Covey Farm and the broad Chesapeake Bay beyond. As Douglass described, the site is midway between the landmarks of Kent Point and Poplar Island.

On New Year’s Day 1834, when Douglass completed the seven-mile walk from St. Michaels to Covey’s farm, he was filled with dread as he recalled the stories he had heard about Covey’s cruelty and frequent use of the whip. It wasn’t long before Douglass found out for himself how terrible Covey could be. The young slave was sent into the woods (behind this church) for a load of wood behind a team of unbroken oxen, with disastrous results and vicious punishment to follow.

This is also the scene of the weeklong Bayside camp meetings, which drew several steamers from Baltimore. In the camp meeting, Douglass observed Thomas Auld experience a conversion, become an exhorter, and yet continue to starve and whip half the members of his household. Religious hypocrisy among the slaveholders of the white Methodist church of the 1830s is a theme in all three Douglass autobiographies. Covey was also known for wearing out knees with daily prayers, “as strict in the cultivation of piety, as he was in the cultivation of his farm.”
— My Bondage and My Freedom.

Easton Star, August 17, 1830

However, it was here that Douglass came into his own when he defeated Covey in a much-celebrated fistfight. In Douglass’s own words, “This battle with Mr. Covey … was the turning point in my life as a slave … I was NOTHING before: I WAS A MAN NOW.” — My Bondage and My Freedom.

As you proceed to Site #4, note the intersection of Pot Pie Road in Wittman. The road leads to Pot Pie Neck, where Douglass’s friend Sandy Jenkins procured a root offered as a talisman. Douglass had the root in his pocket during his fight with Covey.

Site #4 — Lowe’s Wharf — Site of Haddaway’s Ferry

Haddaway’s Ferry ran from here to Annapolis and brought the mail for Talbot County and points north since Colonial days. It is here that steamers of Methodist camp meeting attendees from Baltimore arrived in the hot summers of the 1830s. You can park and look across the Chesapeake Bay as you contemplate Douglass’s most important words from his time on the Bayside of Talbot County. From the waters before you he found his resolve to self-liberate and his resolve to see an end to slavery for all people.

I shall never be able to narrate the mental experience through which it was my lot to pass during my stay at Covey’s. I was completely wrecked, changed and bewildered; goaded almost to madness at one time, and at another reconciling myself to my wretched condition. …

Our house stood within a few rods of the Chesapeake Bay, whose broad bosom was ever white with sails from every quarter of the habitable globe. Those beautiful vessels, robed in purest white, so delightful to the eye of freemen, were to me so many shrouded ghosts, to terrify and torment me with thoughts of my wretched condition. I have often, in the deep stillness of a summer’s Sabbath, stood all alone upon the lofty banks of that noble bay, and traced, with saddened heart and tearful eye, the countless number of sails moving off to the mighty ocean. The sight of these always affected me powerfully. My thoughts would compel utterance; and there, with no audience but the Almighty, I would pour out my soul’s complaint, in my rude way, with an apostrophe to the moving multitude of ships:–

You are loosed from your moorings, and are free; I am fast in my chains, and am a slave! You move merrily before the gentle gale, and I sadly before the bloody whip! You are freedom’s swift-winged angels, that fly round the world; I am confined in bands of iron! O that I were free! …

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. … 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, 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.
— Frederick Douglass, My Bondage and My Freedom

Site #5 — Freeland Farm & Old Martingham

Pull to the roadside 0.15 mile past Broad Creek Road. Old Martingham, to your left on the Miles River, was the seat of the Hambleton family since 1663. The Hambleton family was important in the War of 1812. In Douglass’s time, a large contingent of brothers and sisters controlled most of the land from Emerson Point to Perry Cabin in St. Michaels.

Look to the right and you can see Broad Creek, part of the Choptank River with the abandoned train bridge crossing the creek. (Douglass rode a train across this bridge on his last visit to Talbot County in 1893). The farmland on the Broad Creek side is the site of the Freeland Farm, where young Douglass was hired out from Jan. 1, 1835 to spring 1836. William Freeland’s wife was one of the Hambleton sisters.

“I found myself in congenial society, at Mr. Freeland’s,” Douglas wrote. “There were Henry Harris, John Harris, Handy Caldwell, and Sandy Jenkins.” Douglass considered William Freeland to be a “well-bred southern gentleman … the best master I ever had until I became my own master.” During his time at the Freeland farm, Douglass learned that he was gaining a reputation among the whites as a troublemaker and among the blacks as a hero and leader. He was quick to take advantage of his role as a leader by organizing another school for blacks, but this time the school was kept secret.

On New Year’s Day, 1836, Douglass resolved that this was the year he would become free and began planning his escape. On Easter weekend, with the branches of the Hambleton family gathered at Old Martingham, he and four others (including his uncle Henry Bailey) would take one of William Hambleton’s two sailing log canoes from Emerson Point, round Kent Point and head up the Bay. It would take a full crew to handle the vessel. William Hambleton got wind of the plot. Sandy Jenkins (the “root man”) became frightened and was suspected of leaking some detail. On the morning of their planned escape, they were arrested and forced to walk more than 20 miles tied behind a mounted horse to the jail in Easton. Word spread quickly; at every village along the way, the men were jeered and harassed. Tour #4 includes the site of the Easton jail where Douglass spent a harrowing week, uncertain of his fate.

Site #6 — The Eliza Bailey Mitchell House

213 N. Talbot Street, St. Michaels

The Mitchell House is the small white cabin on the Chesapeake Bay Maritime Museum grounds. The cabin is open daily to Museum visitors. Admission may be purchased at the front gate.

Two years older than Frederick, Eliza Bailey Mitchell was the closest sibling to Douglass. They maintained a lifelong relationship. The two of them had shared experiences under Thomas and Rowena Auld and, as Douglass later claimed, it was Eliza who taught him the art of survival in the face of hunger and abuse. Eliza and her two children were sold by Thomas Auld to her free husband, Peter Mitchell, in 1836 for $100 (a debt which they both worked for almost five years to repay). Peter Mitchell and his brother James were highly esteemed farm managers for the Hambleton family.

Eliza Mitchell was matriarch to many generations of the Mitchell family in St. Michaels and the surrounding area. Her great-grandson James E. Thomas became the first African-American elected to the town commission in St. Michaels and the first elected president of that body. The Mitchell home originally stood on Lee Street on land subdivided from Perry Cabin by the Hambletons. The house was slated for demolition and Commissioner Thomas was a leading force to save it by relocation to the Museum. While at the museum, be sure to see the log canoes and the Edna Lockwood, a 19th century bugeye under restoration. The canoe Frederick Douglass planned to take from William Hambleton would have resembled a cross between a modern racing log canoe and a bugeye.

Tour #3 Ends Here

Although there are many more Douglass sites in St. Michaels to see.
They include:

200 Cherry Street — Home of William and Louisa Bruff — now the Dr. Dodson House Bed & Breakfast

200 Cherry Street

While visiting family in St. Michaels in 1877, Douglass was invited to call on the aged Thomas Auld, who was ill in the second-floor bedroom. (Mrs. Bruff was Auld’s daughter). The much-reported visit was the first time the two men had seen each other since 1836.

Sardi’s Chapel site at St. Mary’s Square

The main Methodist church was located on the town green at St. Mary’s Square. Douglass would have attended with the both the Auld and Covey families.  The Saint Mary’s Square Museum offers an excellent Douglass walking tour of St. Michaels on alternate summer weekends.

Olivet Cemetery

In an iron-fenced area towards the southwest corner of this cemetery, part of the St. Luke’s Parish in St. Michaels, are the graves of many of Douglass’s contemporaries, including Thomas Auld and Lucretia Anthony Auld. Additionally, one can also find the graves of Garretson West, an oysterman who headed the posse organized to break up Douglass’s teaching activities, and that of the Reverend Daniel Weeden, a neighbor of Freeland’s, who believed, according to Frederick Douglass in My Bondage and My Freedom, that “the good slave must be whipped to be kept good, and the bad slave must be whipped, to be made good.”

Long’s Chapel and Cemetery

At the rear of the Blue Crab Coffee Shop across from the library is a memorial for the site of Long’s Chapel, named for Douglass’s friend Rev. John Dixon Long. Long established a church here with help from one of the Hambleton sisters. “In 1853, I established, in St. Michael’s, Talbot County, Md., a Sabbath school for colored persons, slave and free. Previous to its organization, I unfolded my purpose in regard to it to a brother in the church, who advised me to desist from the undertaking, as I was already denounced as an abolitionist.” — John Dixon Long, Pictures of Slavery in Church and State. Long’s Chapel was the beginning of Union United Methodist Church at the corner of Fremont and Railroad Avenue. The coffee shop is the former Freedom’s Friend Lodge #1024, a black mutual aid society begun in September, 1865 as an offshoot from a Baltimore organization.

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