Three Dare households are shown on this map, surveyed in 1824 and published in 1857. We believe that Dare household to the east is Bayside Farm, occupied by the elder Gideon Dare prior to his death in 1820. Meanwhile, the Dare household south of the main east-west road is Holly Hill, occupied by Henry Dare until his death in 1833. It is possible that the household north of the main road was the younger Gideon Dare's property. The abbreviation M.H. marks the site of a Quaker Meeting House; the abbreviation W.H. marks the site of a warehouse serving transport at Allnut's Landing (sometimes spelled Allnutts; later Dares Wharf and today, Dares Beach). Detail from U.S. Engineer Dept., Maj. J.J. Abert and Maj. J. Kearney, Map of the Patuxent & St. Mary's Rivers; survey 1824, pub 1857. The full map is linked from the Calvert County historic maps page.

 

1822: Henry Dare failed to pay a debt

 

Henry Dare failed to pay a debt to Joseph G. Waters and, following a writ of execution on a judgement against Dare, Holly Hill was seized and put up for sale by the sheriff. However, the property did not sell as planned.

 

1825: Holly Hill sold to Nathan Levering

 

Belated sheriff's sale of Holly Hill to Nathan Levering of Baltimore.

 

1832: Holly Hill sold to Thomas Clevely Dare

 

Nathan Levering sold the land to Thomas C. Dare (1779-ca 1838, Henry Dare's brother).

 

1833: death of Henry Dare

 

Henry Dare died.

 

1838: death of Thomas Clevely Dare

 

Thomas Clevely Dare died; his will included the following bequests:

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• Holly Hill to his son Richard S. Dare.

• Bayside plantation to his son Thomas Clevely Dare Jr., "where on he now lives."

• Personal property to his wife Elizabeth S. Dare and, after her death, to his son John G. Dare. Thomas Clevely Dare's will also instructs Elizabeth and son Richard S. Dare to serve as guardians to his 15-year-old son John.

 

1840-1890

 

During these decades, most of what we know is derived from census records, including the Agricultural Schedule of the U.S. Census, often referred to as the Agricultural Census, and available for 1850-1880. Information was also provided by a Chancery Court case, see the 1850-1854 entry below. As reported below, the census enumerations for Richard Dare and Thomas Dare in 1840 and for Richard Dare and John Dare in 1860 name a number of Free Blacks (the usual term for free persons of African descent), several of whom were laborers on the Dare farms. Knowing of the Dare family's Quaker background, we wondered if this presence aligned with their faith's support for abolition. There is, however, a counter-indicator in 1850, when the U.S. Census Slave Schedule lists a Richard Dare as owner of 8 enslaved individuals. At this writing, we are uncertain as to how to interpret these findings.

 

1840: three Dare households, including Holly Hill

 

Comment: in the main enumeration of the 1840 census, people's ages are given as ranges; our more exact age information is primarily derived from later census records and gravestone markings.

Richard S. Dare (1805-1868); information in the chancery court record indicates that this household occupied Holly Hill.

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• Census data reports that this household included Richard S. Dare, his wife Priscilla Allnutt Dare (prob b 1809-d 1858), two Free Black males, two Free Black females, and one enslaved female child. Richard and Priscilla Dare had a daughter Sarah E. Dare; according to the Find-a-Grave entry, Sarah died at age 2 in 1842.

 

Elizabeth Snowden Dare (1784/5-1859, widow of Thomas Clevely Dare, 1779-1838): information in the chancery court record suggests this was the Bayside Farm.

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• Census data reports that this household included Elizabeth Snowden Dare and a white male aged 20-29, almost certainly Elizabeth and Thomas's teenage son John G. Dare (1823-1890). The household also included two male Free Blacks and two female Free Blacks.

 

Thomas Clevely Dare [Junior], 1808-1843 [dates sometimes given as 1810-1845]; location not identified.

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• Census data indicates that this household included Thomas Clevely Dare [Jr], and one male Free Black and one female Free Black.

 

1850: two Dare households, including Holly Hill

 

Richard S. Dare (1805-1868): information in the chancery court record indicates that this included Holly Hill; the extent of acreage suggest that this also included additional land.

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• Census data reports this household included Richard S. Dare, listing him as farmer and planter, and his wife Priscilla Dare [she would die in 1858]. The 1850 U.S. Census Slave Schedule lists a Richard Dare as owning 8 enslaved individuals. We believe that this is the same Richard Dare; however, no other reports that we have seen for 1840-1860 state that he owned more than one enslaved person. The 1850 Agricultural Census indicates that the farm's main cash crop was tobacco (5,000 lbs), although the listing suggests that livestock, wheat, and butter may also have been sold. The decennial census reports real estate valued at $4,000, no acreage stated; the Agricultural Census reports a value of $7,000 and 555 acres.

 

John G. Dare (1823-1890): information in the chancery court record suggests this was the Bayside Farm.

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• Census data reports this household included John G. Dare, listing him as farmer and planter, and his mother Elizabeth Dare [she would die in 1859]; the Agricultural Census indicates that the farm's main cash crop was tobacco (5,000 lbs), although the listing suggests that livestock, wheat, and butter may also have been sold. The decennial census reports real estate valued at $3,000, no acreage stated; the Agricultural census reports a value of $1,800 [difficult to read] and 180 acres.

1850-1854: Chancery Court case, Catherine Dare v. Richard S. Dare

 

Catherine Dare was the widow of Henry Dare. Her claim was for the dower portion of Holly Hill, which her husband had inherited from his father Gideon Dare in 1820. Holly Hill had been sold at a sheriff’s sale in 1825 and later sold to Thomas C. Dare in 1832 and left to his son Richard S. Dare in 1838. A court decision is not included in the case file, but we presume that Catherine Dare’s dower rights were lost when Henry Dare defaulted on his debt and the farm was seized by the sheriff, and the case was decided in favor of the defendant, Richard S. Dare. (Maryland State Archives, Chancery Court Cases, 1850/11/09; Catherine Dare vs. Richard S. Dare. CV. Estate of Henry Dare - Holly Hill. Accession No.: 17,898-7387 MSA S512-9-7364 Location:1/37/4/.)

 

1860: two Dare households, including Holly Hill

 

Four separate rows in the 1860 Agricultural Census associate Richard S. Dare with two farms and John G. Dare with two farms. In both pairs, the two tracts are listed with 337 and 175 acres. We believe that this may indicate that the brothers shared the management of Holly Hill and the Bayside Farm; the total acreage of 512 for the two properties is consistent with earlier reports. The cash crop of tobacco appears in three of the four listings, with yields of 14,000, 11,000 and 7,000 lbs. The farm data also lists horses, oxen, milk cows, hogs, and sheep, and the sale of potatoes and butter.

 

Richard S. Dare (1805-1868)

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• Census data indicates that this household includes Richard S. Dare, a 7-year old white girl named Rachel Ramsey, and two Free Black men, Dennis Blake and Horace Gross. Richard S. Dare's wife Priscilla had died in 1858.

 

John G. Dare (1823-1890)

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• Census data indicates that this household included John G. Dare and six Free Blacks: Jacob Boots (male age 65), Roaney [Ronny?] Boots (female age 40), Eliza Boots (female, age 19), [Julia?] Boots (female, age 14), Tom Boots (male, age 10), and Baby Boots (male infant). John Dare's mother, Elizabeth, who had been living with John, died in 1859. In the 1860 census enumeration, the next household listed after John Dare is an eight-person Free Black family, headed by Samuel Boots. John Dare's name also turns up an 1863 Civil War military registration record although there is no indication that he was drafted.

 

1870: one household, Holly Hill

 

Richard S. Dare died in 1868. The Agricultural Census associates 285 acres with John G. Dare; we have not determined how to account for the reduction from the 1860 total of 512 acres. It is likely that the Bayside Farm and other land to the east was sold at some point prior to 1870.

 

John G. Dare (1823-1890)

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• Census data indicates that this household included John G. Dare and eight African Americans. Six are listed as farm laborers: Samuel Boots, George Hicks, William Smith, George Boots, Jeremiah Boots. The list also includes Barbara Beckett, domestic servant, with her son William, age 6. The 1870 Agricultural Census listing for John Dare states that the farm acreage is 285 with a value of $3,500. It also reports that Dare paid $930 in wages (including board), harvested 1,600 lbs of tobacco (far fewer than in previous years); the total value of all farm products is stated as $1,686. If the $930 labor cost is deducted, net earnings would be $756.

 

1880: one household, Holly Hill

 

John G. Dare (1823-1890)

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• Census data indicates that this household included John G. Dare and five African Americans: Wesley Whillington (Whittington?, servant), Charles Freeland (servant), Barbara Flint (keeping house). W. Henry Flint (hand), and James Parish (servant). Virginia E. Freeland (1832-1900), who joined John Dare as his life companion at some point in this general period, is listed as residing with her brother George Freeland, "two households over" on the same census page.

 

1890: death of John G. Dare

 

John Dare (1823-1890). Buried in St. Paul's Episcopal Church extension cemetery, Dares Beach Road. This a former Freeland-family graveyard.

 

John G. Dare's will

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• " … I give and devise unto the said Virginia E. Freeland the Farm or Plantation whereon I now reside containing Three hundred acres more or less, to her and her heirs and assigns in fee simple…." Calvert County Wills VCC1:110

1900-2017

 

During these decades, some of what we know is derived from deeds and census records, supplemented by personal recollections from Thomas B. Turner MD (1902-2002) and his daughter Anne Pope.

 

1900: death of Virginia E. Freeland

 

Virginia E. "Jennie" Freeland (1831-1900). Buried in St. Paul's Episcopal Church extension cemetery next to John G Dare. This a former Freeland-family graveyard.

One member of the John Dare (Holly Hill) household during the 1890s and perhaps even earlier was Virginia "Jennie" Freeland Lyles (1878-1970), Virginia E. "Jennie" Freeland's niece. In 1902, Lyles (by then married to George Turner) gave birth to Thomas B. Turner; years later, thinking of her and the family association with John Dare, Turner commented, "I know one Dare who never married. Uncle John we called him, Uncle John Dare." (From a recorded interview, 22 September 1995, identifier aclt-sca-cf_C014A.)

 

1900-1901: Acquisition of Holly Hill by Jennie Lyles (1878-1970), soon to marry George Turner (1868-1948)

 

Regarding her grandparents George Dorsey Turner (1868-1948) and Jennie Lyles Turner (1878-1970), Anne Pope described the circumstances in a 2017 email.

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• "Jennie [Lyles] grew up there with her Aunt Jennie [Freeland] (for whom she was named) after her mother died. I have a diary kept by my grandmother while she was living there that talks with great excitement about Mr Turner coming to visit. When the farm was put up for sale, in quite a romantic gesture, Granddaddy bought it for her although it was not actually in her name until he died and left it to her in its entirety. . . . My Grandfather Turner loved buying land and bought hundreds of acres around Prince Frederick and of course Holly Hill. He loved to own it and he loved to walk it."

• The legal details in some of the deeds related to the acquisition add some complications as, apparently, various Lyles and Dare relatives sorted out claims to parts of the property in December 1900 and April 1901. In these deeds, Jennie is identified as Virginia F. Lyles. The matter seems to have been brought to conclusion in another "sorting out" deed dated 19 November 1901, that names the parties as George D. Turner and Virginia F. Turner and describes the outcome obtained by trustee J. Frank Parran:

• " . . . the said Trustee, after complying with all the previous requisites of the decree, did on the 24th day of June in the year one thousand nine hundred and one sell unto the said George D. Turner and Virginia F. Turner at and for the sum of eight hundred dollars, current money, the aforesaid leasehold property situate in Calvert County . . . containing three hundred acres more or less."

1917: Thomas B. Turner (1902-2002) worked at the farm

 

Thomas "Tommy" B. Turner, George and Jennie Turner's son and later a physician and Dean of the Johns Hopkins University School of Medicine, recalls working on Holly Hill as a teen-ager:

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• "Eventually at about age 15, I became my father’s 'foreman' during the summer, working along with the hired men--about a half dozen blacks and whites--planting, cultivating, and harvesting corn and tobacco. My immunity to farming was thus acquired early!" (From Part of Medicine, Part of Me, privately published 1981)

• In an reminiscence, Thomas Turner also recalls his father passing along tales learned from an African American storyteller:

• "My father had a good sense of humor and was somewhat of a raconteur. He began early telling me 'Uncle Remus' stories which had been told him as a child by an old black man on his grandfather [Thomas Bourne] Turner’s farm. [This farm was across the county to the west, near a place called Chitron Neck.] Since my father was born in 1868, these stories were being told well before Joel Chandler Harris put them in a book first published in 1880. Moreover, many of the tales told to me about Brer Rabbit and Brer Fox differed substantially from those recorded by Harris, so presumably they were a part of the early black culture in America. These were wondrous stories which have now delighted four generations of my family; in most of them Mr. Rabbit was the lazy fellow always devising ways to get something for nothing by outwitting some hardworking fellow, usually Mr. Fox or Mr. Dog.