“My life has been distinguished by two important events, dated about twenty-six years apart,” Frederick Douglass declared to an audience at Baltimore’s Bethel African Methodist Episcopal (AME) Church in November 1864. “One was my running away from Maryland, and the other is my returning to Maryland to-night.” If Baltimore, Maryland, was a bona fide source of Douglass’s unique gift, his claim that he was “standing on the very spot where I first came to worship” was a crowd-warming flourish, but inaccurate (SDI 4:41, 39). Douglass attended the black-run AME church near Old Town as his adult ambition climbed in the late 1830s; as a child he was nurtured by black Methodists closer to home, in Fell’s Point. In 1891, Douglass correctly identified the first church he joined as the Centennial Methodist Episcopal Church of Baltimore. “I was admitted to membership in this church on November 18, 1831.… When I joined the church the congregation worshiped in … what at that time was called Strawberry alley,” he recounted.¹ The Strawberry Alley meeting house was Baltimore’s oldest permanent Methodist place of worship. A majority black congregation by 1802, unlike Bethel on Saratoga Street, Strawberry Alley never attained full autonomy or ordained its own ministry. While Douglass noted the AMEs in his journey out of bondage, it was a stew of worship houses and black neighborhoods, near the water’s edge and in more distant locales of Baltimore, that steered his famed pursuit of abolitionist literacy.²

Eight-year-old Frederick Bailey arrived in Baltimore in March 1826. The boy was deposited at the home of shipwright Hugh Auld, the brother of Thomas Auld, who, after his wife Lucretia’s death in 1827, would become Bailey’s owner. Hugh, his wife Sophia, and their two-year-old son Tommy lived on Aliceanna Street, at the corner of Happy Alley, when Bailey arrived. The couple soon moved to 37 Philpot Street, a few blocks south. Both streets were located in Fell’s Point, a promontory on the Patapsco River founded by landowner William Fell in 1763 and the shipbuilding hub of early republican Baltimore (Figure 1.1).³

Figure 1.1 Map of Baltimore in 1838. (a) Auld family home at 37 Philpot Street; (b) Strawberry Alley Methodist Church; (c) Sharp Street Church; (d) Bethel AME Church on Saratoga Street; (e) James Mingo’s house at the corner of Happy Alley and Wilkes Street. Thomas G. Bradford, An Illustrated Atlas, Geographical, Statistical, and Historical, of the United States, and the Adjacent Countries (Boston: Weeks, Jordan, 1838).

Courtesy of the Johns Hopkins University Sheridan Libraries

While some travelers saw an ancient grandeur in Baltimore Town – “the city, seen from the bay, might be mistaken for Rome” – it was also obvious to others that “the Point,” the shipyard east of the harbor, was “dirty and unattractive.”⁴ This early national divide between territories cut by the Jones Falls was as polar as the Falls itself. Upstream the Jones Falls provided the commercial engine propelling local grain mills, only to become a sludge-like, fetid canal filled with sewage as it emptied into the Basin, where the Patapsco River reached land, forming the town’s natural harbor. The Falls practically separated the city into east and west segments and was a consequential landmark and obstacle for the young boy. The most elegant passage was a bridge along Baltimore Street, a mile north, and the easiest, the wharf route from Pratt Street, where the coffles of enslaved people marched at night to the clipper ships and steamboat packets for sale to Petersburg, Charleston, and New Orleans. The first difficulty for the boy was to overcome the taunt that he was country, from Maryland’s Eastern Shore, and join the Point lads in rock battles against boys from Baltimore Town. Freddy Bailey, who already had a deep scar over his eye from battles with iron shavings at Wye House, made friends and joined the fight.

Bailey always lived in the city’s second ward, one of four large cantons of urban Africans and their descendants. Baltimore’s total 1830 population was 80,620 and, of that, 18,910 was African American. Four-fifths of these black people were legally free, the largest concentration of them in any US city; they maintained their liberty as launderers, carters, seamen, caulkers, porters, cooks, cleaners, and hacks. In Baltimore, it was becoming increasingly unusual to be enslaved.⁵ The customary habit of free black people in the city was to deliberately occupy public space. Streets spilling over with “‘colored gentlemen’ who frequent the outside of the Sharp street meeting house … clustered around the steps,” numerous black male stevedores and female hucksters unencumbered by the supervisory logic of slavery, blacks who sued in open court, fought back when struck or insulted, and defended themselves against kidnappers trying to render them into slavery, contributed to the city’s nickname “Mobtown.”⁶

Between 1826 and 1833, the most important address for Bailey was the Philpot Street house, on a section marked by two brick dwellings and typically called “Despeaux’s Wharf,” after the Point’s most prominent shipbuilder, the white refugee from Saint-Domingue Joseph Despeaux. Bailey remained there through March 1833, when he was returned to Talbot County on the Eastern Shore. Slaveholding remnants of the Despeaux family lived next door, at 33 Philpot, at the southwestern corner of Wills Street. In two households, Frances Despeaux and her daughter Ann enslaved twelve people, including female Louisa, born in 1821, and males Ben Dority, born in 1807, and LaFleur, born in 1806. Although Philpot Street ran only three blocks, several of the households retained enslaved people. In 1830, toward the end of Bailey’s boyhood years in Baltimore, there were seventy-seven people of African descent living on Philpot, Block, and Dock Streets – Bailey’s neighborhood – twenty-seven of them free people, including seven black boys in his age category, one of them free.⁷ These are among the people he saw everyday as he fetched water, wood, and coal, and scurried to Mr. Aburn’s shop for flour or bacon, eventually walking with Tommy to school.

The black households on Philpot and Block Streets offered a concrete lesson to young Bailey in self-governed liberty. Four free blacks lived with Charles Lawson, and Robert Bond’s household contained three free elderly black adults. Even enslaved Hester Williams lived alone, with a woman young enough to be her daughter. While these Baltimoreans inhabited slight wooden frame houses, and Hester Williams probably occupied a shanty, Fred roomed in a household of twelve, possibly in a three-story brick house on a twenty-foot lot, like the buildings on the Despeaux property at Wills and Philpot.⁸ Though not materially prosperous, this black community could dress his hair, teach him songs and rhythms, welcome him into organized Christian religious practice, and provide an example of life unaided by white overlordship.

Fred had received the beginnings of religious instruction from an enslaved man named Isaac Copper at Wye House. In Baltimore, Fred’s thirty-year-old mistress Sophia Auld was enrolled as a probationer at the Wilkes Street Methodist Church, pastored by Beverly Waugh, a visitor to the Auld home. Bailey accompanied her to church, but that tradition ended before long. In an early shift away from intimate interracial domestic to intraracial neighborhood alliances, he befriended his pious black neighbor Charles Lawson and started to attend the Strawberry Alley church with him. A ropemaker’s drayman, Lawson became “spiritual father” to orphan Bailey. “I loved him intensely,” admitted Douglass, “and was at his house every chance I got.” Beyond providing the religious instruction and a private space managed by black elders, Lawson was the first African American named in Douglass’s narratives in possession of a book. Defying the Aulds, Douglass accompanied Lawson “to prayer-meeting, and spent much of my leisure time with him on Sunday.” Douglass’s statement about venturing to Lawson’s indicates habitual practice over the years, one where he was recruited in the clandestine activity of reading, memorization, and reasoning. While his putative owner Hugh Auld was “averse to my going to Father Lawson’s,” Douglass persisted in the relationship, which stimulated his literacy and his association with other determined blacks (BF 96, 95). The boy’s defiance of his white master to develop a relationship with a black neighbor and to master the complex world of free black men was the beginning of a series of self-conscious acts that would culminate with his escape from the city in 1838.

Lawson may have been special, but he was not singular. The large free black community significantly fed Bailey’s appetite for literacy, abolitionist discourse, and disciplined spirituality. While Lawson attended nearby Strawberry Alley Methodist Church, his name on the Baltimore City Station registry of 1825 means that he was intimate with congregations of the Town, some of them running into the thousands, such as the parent church of Baltimore’s black Methodists, the Sharp Street Church, west of the Jones Falls and south of Pratt Street, which traced its origins to 1787.⁹ Lawson apparently contributed to Bailey’s ability to bridge the “low water” seafaring black communities of the Point and the refined barbers, domestic servants, and cordwainers operating three schools for black children in the Town. By 1832, Bailey belonged to a black social network of information and culture that included Strawberry Alley and Sharp Street, the Point, and the southwest neighborhood of the Town – a circuit that would later include the northern portion of Saratoga Street, where he lectured in 1864. He at least visited the historic Sharp Street Church during the cholera epidemic of 1832, when black residents were “all invited up to this church to receive advice from Dr. [Lewis G.] Wells,” the city’s prominent black physician and preacher.¹⁰

Wesleyan Methodism had its organizational stronghold in Baltimore, where it had attracted eager black worshippers from the 1770s, drawn to the charismatic vernacular approach of the preachers as well as to the antislavery doctrine. In 1780 in Baltimore the Methodist conference had included an ordinance to “pass our disapprobation on all our friends who keep slaves,” and African American Methodist elder Harry Hosier, known as “Black Harry,” served as a revered figure.¹¹ Nonetheless, segregated pews and communion, and the sluggish advance of blacks as officiants within the Methodist ranks, necessitated the acquisition of ground and buildings and the creation of all-black congregations in Baltimore. By 1830, the city counted four black Methodist churches: Sharp Street, in sight of the Pratt Street slave pens; Asbury Church and Bethel in Old Town; and Strawberry Alley in Fell’s Point. The largest and most prestigious was Sharp Street.

The church Bailey attended most frequently, “low and plain” Strawberry Alley, had been “given to the colored society” for so long that people called it “Bethel on the Point,” conflating it with the larger, independent church on Saratoga Street.¹² Behind the pulpit was a blue circle with the cry of Egyptian slave Hagar, “Thou, God Seest Me,” painted in gold. In the region, black Methodist services (the sermons delivered by whites assigned by the diocese) were known to be audible “at half a mile distant,” particularly the “devotional songs.” European travelers and the black ministers themselves noted the emotional vigor, or “wild enthusiasm,” of the church meetings.¹³ Keen-witted and sensitive to his own emotional discomfort and that of other people, Fred Bailey, who would become the earliest black person to write about the complexity of enslaved black people’s music, lived about four blocks away from a black church for seven years. The space was significant enough that in the final decade of his life, Bailey returned to the same Strawberry Alley, purchasing several lots and building five brick row houses on the block where the meeting house had once stood.¹⁴

At the request of the boy, Sophia Auld had introduced Bailey to reading by teaching him the alphabet and simple words, until she was sternly rebuked by her husband, who delivered the legendary injunction that literacy would spoil the boy for slavery. Bailey went on to piece an education together, using cast-off Webster’s spelling books and hymnals and tempting “the dear little fellows” from his block with leftover biscuits (NL 34). Until now it has been assumed that Douglass’s Narrative of the Life of Frederick Douglass, an American Slave (1845) and My Bondage and My Freedom (1855), emphasizing the possibility of interracial ties, had afforded a complete view of a lengthy process, peaking with the narrator’s purchase of Caleb Bingham’s The Columbian Orator at Nathaniel Knight’s shop on Thames Street. Since the work of Dickson Preston in 1980, the consensus has been that the “little boys” who said “that they were going to learn some little pieces out of it for the Exhibition” and from whom Douglass first heard about the book were the white boys of Philpot Street (BF 90).¹⁵ However, Baltimore opened its public school system for whites in 1829, enrolling that year 269 pupils throughout the city, the number climbing to 640 by 1832, with few more than a dozen instructors.¹⁶ Among the very young sons of the mechanic class in the working-class part of town, Bailey was unlikely to gain the sole impetus for what is understood as his prime early literate achievement.

The free community orbiting the Strawberry Alley meeting house offers another way to grasp the arc of Bailey’s literacy toward abolitionism. Commemorating Douglass’s death in 1895, Jane Marsh Parker interpreted the famed book purchase by pointing to the requirements of a black audience, writing that he wanted The Columbian Orator “[so] that he might learn something to speak at the Sabbath-school exhibitions of the free negroes, which he attended by stealth, and where he was beginning to shine as an orator.”¹⁷ A competition based out of the black Methodists at the East Baltimore Station makes sense considering that Strawberry Alley was the most consequential nearby institution requiring black literacy as a functional condition for membership. Strawberry Alley is the church Douglass refers to when he writes that when he “met boys about Bethel church, or any of our play-grounds, I entered the lists with them in the art of writing, and would make the letters which I had been so fortunate as to learn, and ask them to ‘beat that if they could.’” And it is also undoubtedly about the dullness of the Sabbath school at Strawberry Alley that Douglass directed this telling comment: “In Baltimore, I could, occasionally, get into a Sabbath school, among the free children, and receive lessons, with the rest; but, having already learned both to read and to write, I was more of a teacher than a pupil” (BF 98, 114).

Yet, there were schools taught by black scholars in Baltimore where more strenuous exhibitions of learning took place: St. James African Episcopal Church on North Street, near Bethel, where William Levington instructed seventy students, free and enslaved, by the late 1820s; John Fortie’s school connected to the Methodist churches of Old Town; and William Watkins’s academy, near the Sharp Street Church.¹⁸ As Hilary Moss notes, visitors to Baltimore were often surprised to find black schooling so prevalent in the city; a free black New Yorker remarked in 1839 that “even Baltimore, in the slave State of Maryland, has schools superior to ours.”¹⁹ Bailey relished the chance to read and speak learnedly among other black people; the occasion to do so conveyed prestige. He noted that “if a colored preacher could be found sufficiently capable and intelligent to instruct us and preach to us, he was looked upon by the colored people as a marvel.”²⁰

During Bailey’s years in Baltimore, the most marvelous black preacher on account of his erudition was William Watkins.²¹ Watkins led the William Watkins Academy for Negro Youth, a school offering Latin and Greek and conducted at the church near the corner of Sharp Street and Camden Street. The academy produced two graduates that Bailey knew later and could have known as children in the 1830s: Watkins’s niece Frances Ellen and his son William J. Watkins. The most highly praised black female writer of the nineteenth century, Frances Ellen Watkins Harper was such an outstanding scholar and poet that her book Forest Leaves was published in Baltimore sometime after 1845; she is still credited with publishing the first short story written by an African American woman, “The Two Offers” (1859).²² Her cousin William J. Watkins would leave Baltimore in 1853 to join Douglass as associate editor of Frederick Douglass’ Paper.

Uncle and father William Watkins had graduated from Maryland AME bishop Daniel Coker’s school, where he had certainly recited Coker’s 1810 publication, A Dialogue between a Virginian and an African Minister, the first black abolitionist pamphlet published below the Mason–Dixon line. Raised and married in the Sharp Street Church, Watkins was an extraordinary scholar and an active participant in the American Moral Reform Society, which promoted education, temperance, economy, and universal liberty. In public addresses during the mid-1820s, Watkins insisted that “the descendants of Africa” were “as capable of intellectual improvements as the Europeans, or people of any other nation.”²³ His most radical public venture involved the creation in 1827 of the Legal Rights Association, with James Deaver and Hezekiah Grice. Attempting to produce legal frameworks for “birthright citizenship” to contest the application of laws aimed at curtailing black rights, the men hired prominent Baltimore attorneys such as John H. B. Latrobe and later William Wirt, former US attorney general, to prepare a legal brief interpreting the Constitution that would uphold native blacks as full citizens.²⁴ Adherents to the central argument of the Declaration of Independence revisited the Constitution as a document capacious enough to guarantee black rights, a move that Bailey himself would later become known for. Watkins wrote regularly for Benjamin Lundy’s Baltimore abolitionist paper Genius of Universal Emancipation, shaping William Lloyd Garrison’s early views and, when Garrison started the Liberator in 1831, Watkins published articles with him. He used the pseudonym “A Colored Baltimorean.”

In the years between 1836 and 1838, Watkins took stands to boycott slave-made goods and bemoaned the condition of the black clergy, unable “to supply the intellectual wants of the colored population.”²⁵ During his famously dry public addresses, Watkins was unbending in his advocacy of classical education and probity in a way that Bailey went on to share. Addressing a Philadelphia audience in August 1836, Watkins described the profit of academic instruction to people like then eighteen-year-old Bailey:

Bailey had the opportunity to cross his path when Watkins made his regular rounds across the Jones Falls to the Strawberry Alley meetings “to discharge his obligations as a local preacher.”²⁷

In 1836 Bailey returned to Baltimore from Talbot County field slavery and in Fell’s Point achieved salaried success as a professional caulker. He began to range fully beyond the Point’s “pungent fragrance of boiling pitch” and into Town, where he moonlighted as a butler.²⁸ The abolitionist attitudes of literate blacks like Bailey, willing to use violence to free themselves, challenged the delicate public positions of the church officials. In fall 1835, trustees of the Strawberry Alley church had had to assert their own neutrality in public, deploring “mistaken, hot headed zealots, [who seek] to plunge the country into anarchy and discord, and to deluge it with torrents of blood.” The black clergy, joined in print a few weeks later by more prominent ministers such as Bethel’s Nathaniel Peck, John Fortie of Sharp Street, and William Levington of St. James, were especially having to appear to forsake “the vile, mischievous, and incendiary publications, now so industriously scattered abroad.”²⁹ Frederick Bailey knew these trustees, such as James Wilson, whose “eloquence” he noted alongside that of William Douglass, the erudite black Episcopalian who left Baltimore to head St. Thomas African Episcopal Church in Philadelphia (SDI 4:40). At least one of Bethel’s ministers was also a professional caulker living in Fell’s Point, Charles Johnson, whom Bailey consulted with and thought “a good colored man” (BF 95). Impatient with acts of public conciliation, Nathaniel Peck favored migration to the Caribbean, and embarked shortly on a fact-finding trip to Guyana and Trinidad. Before the trip, Bailey had sat in a pew at Bethel and heard Peck “thunder the gospel into sinners’ ears” (SDI 4:40).

By that time Bailey was a marvel, a teacher gathering pupils wherever he went. He instructed “secret night-school scholars” at houses on Wolfe Street, the Point neighborhood where the black caulkers abounded.³⁰ “My first effort in instructing colored people was commenced here. I opened a night school on Wolfe street, and afterward one on what was then called Fleet street. Both were well attended, and I found my work profitable and pleasing.”³¹ He became known in secret organizations at the homes of important black people, regularly visiting the dwelling of John Mingo, the radical son of the pioneer Sharp Street Church family of James Mingo. The Mingos lived in Happy Alley, in the center of a block with twenty contiguous households of black Americans. Mingo’s frame house in this densely black zone was the location of the East Baltimore Mental Improvement Society, a debating club of free caulkers; Frederick Bailey enjoyed “a prominent part in its debates,” insisting that he would not cease his antislavery disputations before reaching the US Senate (BF 182).³² On Sundays, fellow black caulker and debater John Chester hid with Bailey “under ship’s bottoms and behind logs of ship timber” to become fully literate and probably also to examine incendiary pamphlets.³³

The stealthy acts of black literacy in Happy Alley and Wolfe Street mounted to deeds of greater resistance. The watermen Washington and Jeremiah Stanley lived between Wolfe Street and Star Alley on Wilk Street: Bailey apparently used the seaman’s identification certificate belonging to one of them in his September 1838 locomotive escape from the city.³⁴ Defiance, physical and intellectual, attracted other blacks to Fred Bailey, but also characterized freemen in Baltimore at the moment of his flight. At the end of August 1838, as Bailey and his intended Anna Murray finalized the plot for his running away, a watchman was beaten near Sharp Street Church by the black men from the neighborhood’s doorways, stoops, and corners. Understood well by Bailey, the interracial violence was not simply the work of ruffians “standing about the doors,” but an assault by black Baltimoreans against sentinels of the hated slave regime.³⁵