“A Highly Regarded Citizen” of Windsor, Born Enslaved

Edward Hill c.1885, from his Hartford Times obituary.

Almost one hundred years ago, on March 1, 1928, a man in his 70s died in his home on Elm Street. This man, Edward Hill, whose photo appeared in his obituary, had lived in Windsor for almost 60 years and was a successful farmer, a property owner, an active member of Grace Episcopal Church, a constable, and a member of the volunteer Windsor Fire Company. He and his wife of 24 years raised an adopted daughter, who became a schoolteacher in Springfield, Massachusetts.

None of this is particularly remarkable—until you learn that Edward Hill was a Black man who was born enslaved.

His obituary in the Hartford Times began, “Edward Hill, one of Windsor’s best known and most respected citizens, died late last night at his home on Elm Street following a long illness. He was a native of New Bern, North Carolina, and was born a slave. He was nine years old when the Civil War broke out and soon after its close came north with his brother, Robert Hill.”

An Improbable Journey to Windsor

Edward Hill’s records indicate birth dates ranging from 1850 to 1857; this level of uncertainty for a once-enslaved person is not uncommon. The earliest record we could locate of someone who might possibly be Windsor’s Edward is the 1860 federal census, which lists an Edward Hill, age 8, residing with Caroline Hill, age 47, and Emeline Hill, age 37, all Black “free inhabitants” of New Bern, North Carolina. This census doesn’t list relationships, so Edward can be presumed to be the child of either Caroline or Emeline, but it is unclear which. Caroline’s occupation was washing, and she owned real estate valued at $1,000.

When Windsor’s Edward Hill married in 1888, he reported that his parents were named Buckner and Catherine. “Catherine” is close enough to “Caroline” that either name could have been mis-transcribed by the census enumerator or city clerk. We could not find a census record for a Black man named Buckner Hill in North Carolina in the early-to-mid 1800s, but if he was enslaved, that is unsurprising. Federal censuses before 1850 only named heads of households and just counted the rest of the people in the house.

There is another possibility for Edward’s father. Given that Edward Hill was usually described as mixed race, it’s not a stretch to imagine that he was the product of an enslaved woman and her enslaver.

One obituary claimed Edward was freed from slavery at age 9. We’re unable to determine the exact path, but by the time he was 20, Edward Hill had already taken an unlikely journey—from a young, enslaved child in North Carolina to a free farm laborer affiliated with two of the most prominent families in 19th-century Windsor, the Haydens and the Filleys.

Edward’s Hartford Daily Courant obituary stated that he came to Connecticut “shortly after the Civil War to work for Judge H. Sidney Hayden.” Judge Hayden, a probate judge and state legislator, was a towering figure in Windsor; he owned and developed much of the land in Windsor center. Interestingly, Judge Hayden spent fifteen years in the 1830s and 1840s operating his family’s store in South Carolina, where the family enslaved 14 people. Although we’ve yet to find a direct link between Edward and Hayden that would explain Edward’s move to Windsor, Edward had multiple connections with the judge in town, including being very close neighbors and both attending Grace Episcopal Church.

By 1870—perhaps a few years after arriving in Connecticut—Edward was living in the home of Horace H. Filley. Edward and his brother Robert were working as tobacco sorters and farm laborers. Horace’s son William was a tobacco buyer and the family had begun growing the crop. The Filleys were descendants of a Windsor founding family and prominent town residents who played important roles in commerce and the community from the 1600s through the 1800s. It appears that Robert continued to work as a farm hand for the Filley family for several decades, while Edward eventually acquired his own farm and branched out into other work.

Edward’s Life in Windsor

By 1880, Edward was living in a boarding house that was adjacent to the Young Ladies’ Institute, a school for girls founded by Judge H. Sidney Hayden. Also residing in the boarding house were two Black female servants (one of whom was Rhoda Hicks, who eventually married Robert), three white teachers, and seven students. Presumably all were staff or pupils at the school, which employed Edward as a janitor for more than two decades.

Young Ladies’ Institute at 260 Broad St., c.1880. Edward Hill (possibly the man on the far left in the background) worked here as a custodian for over 20 years. This school later became the Campbell School for Girls, and then the Campbell Apartments. The buildings were town down in 1976, and the site is now the drive-thru for Windsor Federal Savings Bank (as of 2024). | WHS collections 2010.1.48

Throughout their years in Windsor, both Edward and Robert lived in the neighborhood to the west of Broad Street, often next to one another. During this time, the brothers and their families lived among a small cluster of African American families in Windsor center, close to a larger neighborhood around Cook Hill Road.

In 1881, Edward, then in his mid-to-late-twenties, was charged with “bastardy”—fathering a child out of wedlock—by a Black Windsor resident, Hester Johnson. Although he denied the accusation and several of the “ladies of Windsor, connected with the seminary and otherwise” testified to Edward’s “general good character and good behavior,” judgment was rendered against him. Edward was required to pay court costs and child support until the child reached the age of four, an amount estimated at four to five hundred dollars. The Hartford Daily Courant article about the case noted that “Hill has property in Windsor worth a thousand or fifteen hundred dollars,” though 1880 tax records show him owning property valued at only $350. While it’s impossible to say whether this was a just outcome, this incident indicates that Edward associated with both the Black and white populations of Windsor. It also suggests he might have had a child living in Windsor.

Edward eventually married another African American transplant from the South, an Alabama woman named Sallie Tarrant, in 1888. By 1900, the Hill household also included an adopted daughter, Katharyne, age 13.

Edward’s and Robert’s houses at 47 and 53 Elm St., as they look in 2025, probably somewhat modified from when the Hill brothers lived there. | Photo by Michelle Tom

By 1910 Edward and Robert lived next to one another in houses owned by Edward. Robert, who rented 53 Elm Street, was a widower; his wife Rhoda had died in 1902. Edward lived at 47 Elm Street with Sallie and Katharyne, who by that time was a 22-year-old schoolteacher. The two houses back up to where today’s Geissler’s grocery store sits. Edward’s property also included a barn and his farm, which he owned outright.

The next years brought a series of personal changes to Edward. In 1912, Sallie died of tuberculosis at the age of 46. The same year, Katharyne married and moved to Springfield, MA to begin a family. In 1917, Robert died of heat stroke.

Part of the Windsor Community

An active member of the Windsor community for decades, Edward conducted business and participated in civic and religious organizations side by side with his fellow townspeople, who were predominantly white. He volunteered and worshipped with many of the town’s most prominent citizens, who bore still-familiar surnames such as Filley, Hayden, Clapp, Phelps, Mack, Barber, and Fitch. Edward was deeply and widely connected in Windsor.

On November 9, 1882, for instance, Edward was among several men proposed and accepted for membership in the Windsor Fire Company. To the best of our knowledge, he was the only Black member during his service in the organization (and for long afterwards). Likewise, Edward was a longtime worshipper at Grace Episcopal Church, where he and his family would have been among the few, if not the only, Black members.

Other town records and newspaper articles reveal additional aspects of Edward’s life in the community. Censuses describe his work as “farm laborer” to “general jobber.” Indeed, his occupations were quite varied. In addition to tobacco farming and maintaining the facilities at the Young Ladies’ Institute, he served as a town constable, directed the laying of bricks in front of the post office, dug a grave, and “[cared] for lawns for several residents in Windsor.” The town of Windsor paid Edward for janitorial work in Town Hall for years, as well as for “erecting booths” for an election.

Windsor voting records show that Edward voted regularly, beginning as early as 1875 and continuing at least through the 1910s. Additionally, tax records demonstrate his gradual accrual of property over the decades. In 1880, the value of his property was $350, including one horse and two carriages/wagons. By 1890, his taxable property of $1,000 included two houses, and in 1900, he also owned a bicycle and a musical instrument. In his tax record of 1914, Edward owned property valued at $3,450, including the two homes, a barn, two-and-a-half acres of land, a horse, and a musical instrument. Although Edward’s obituary in the Holyoke Transcript-Telegram said that “He was reported to have left a fortune of nearly $150,000,” we can find no evidence that Edward accumulated wealth of that nature, which would approach three million dollars today!

“A Much-Beloved Citizen”

Edward lived in his Elm Street home until 1928, when he died of gangrene and chronic nephritis at age 71; he and Sallie are buried in Palisado Cemetery. He was survived by his foster daughter Katharyne, four grandchildren, three cousins, and a niece, to whom he left his estate.

Edward and Sallie Hill’s grave in Palisado Cemetery (prominently located near the front by the parking area). | Photo by Michelle Tom

The Courant lauded Edward as a “long-time resident and much-beloved citizen of Windsor. … He was always a joy to the youngsters of the town in the old days because of his ready wit and his excessive good humor. Anyone who obtained his services for any piece of work was satisfied that it would be done efficiently. He typified the best of the Southerners who came North directly after the war.” This obituary was almost certainly written by Carlan Goslee, a reporter who was also a member of Grace Episcopal Church and would have known Edward personally.

This journey of Edward Hill—from a childhood of slavery to a well-regarded life as a businessman and property owner, and a trusted and prominent member of Windsor’s community—was an unlikely and impressive one. The echoes of Edward’s time in Windsor resounded into other lives, and in an upcoming article, we will explore the legacy of Edward Hill’s journey to Windsor through the compelling life story of his foster daughter, Katharyne, who became a civil rights leader in Springfield, Massachusetts.

By Sarah Gilligan, WHS board member and volunteer