Finding Richard Loockerman in Denton, Caroline County, Eastern Shore of Maryland

Pictures above: Image 1. House at the site of Richard “Dickey”Loockerman’s plantation Bennett’s Toulson in Denton, Maryland. Image 2. Landing near Bennett’s Toulson. Image 3. Richard Loockerman c. 1803 by Robert Field (1769-1819).

Recently our director Barbara Goyette and curator Rachel Lovett had the opportunity to visit Denton in Caroline County on the Eastern Shore of Maryland. They spent the day two members of the Caroline County Historical Society J.O.K Walsh and Patricia Guida. They toured the Museum of Rural Life in Downtown Denton, soaked in the local culture having lunch at a local pub, and did a driving tour of Richard’s former plantation and neighborhood. They were in pursuit of the details surrounding the life of one of our former inhabitants Richard Loockerman who is one of our most provocative and mysterious characters.

Caroline County has the honor of being the oldest continuous community that has their main economy based in commercial agriculture. The area is made up with large farms, these days mostly poultry farms.

Richard “Dickey” was born in 1783 the only child of his father Richard Loockerman Sr. who owned the plantation Bennett’s Toulson in modern day Denton.  The property, was originally owned by Dickey’s grandfather John Loockerman Jr., who had divided his original 930 acres between his two sons Jacob and Dickey’s father Richard Sr.

Richard Sr. was a veteran of the revolutionary war and married twice, but Dickey was his only child. Unfortunately, Richard Sr. died in 1792 at age 42, when Dickey was just nine years old. It is unclear if Dickey’s mother was his father’s second wife Ann or a woman by the name Mary “Polly” Markland who may have been a common law spouse, as payments were made to her from the estate of Richard Loockerman Sr. for a dozen years after his death.  Illegitimate but acknowledged children were not uncommon in this period, like Benedict Swingate Calvert son of Charles Calvert, Fifth Lord Baltimore or the wealthy Charles Carroll of Carrolton, Signer of the Declaration of Independence.

Upon his father’s death Dickey became a guardian of his uncle Jacob who owned the southern half of Bennett’s Toulson. In his father’s will his instructions were ” I request that my brother Jacob will be mindful that my son Richard shall be liberally educated that he may be qualified for and made to apply to some genteel business.”

Uncle Jacob then rented out the land and some of the enslaved population while raising Dickey, and produced an annual income of 150 pounds, which for the time was a good sum. Jacob oversaw Dickey’s education diligently. There are charges made for silk and cashmere to outfit Dickey. He was sent to boarding school in Easton and Chestertown before coming to Annapolis in March of 1800 to attend St. John’s College. He graduated in 1802 and during his time in Annapolis society met Frances “Fanny” Chase, the beautiful eldest daughter of Judge Jeremiah Townley Chase and his wife Hester.

The couple married October 1st, 1803. Silversmith William Faris, recorded the event in his diary saying “Saturday October 1 a fine day. this evening Jeremiah Chace’s daughter Miss Faney Chace is to be married to Mr. Richard Lockerman, of the Eastern Shore.”

Upon their marriage their miniatures were painted by English born artist Robert Field (1769-1819) who was then living in Annapolis. Dickey and Fanny began spending time at Bennett’s Toulson in Caroline County during the early years of their marriage, along with Fanny’s younger sister Matilda, and her father Judge Chase. The relationship between Dickey and his father in law Judge Chase appears to be quite strained. Dickey took out loans from his father in law in 1808 and 1810 and was able repay a portion back in 1816 but not the full amount. Dickey mortgaged part of Bennett’s Toulson and another property in southern Caroline County on the Choptank river to his father in law. Jefferson’s embargo during the War of 1812 may be have been a contributing cause to Dickey’s financial woes.

Judge Chase became alarmed the young couple were spending so much time away from Annapolis and in order to attract them back  he purchased a large home with four acres nearby to his home on King George Street in 1811. The house was originally built in 1774 by architect William Buckland for Matthias Hammond, who actually never lived on the property. It would have been customary for Judge Chase to give the house to Dickey, as his daughter Frances, as a woman, could not hold property. Chase never gave the house to Richard and made it clear it was for Fanny’s sole use, though Richard could live on the property with his family. Fanny and Dickey had a total of ten children, seven of whom survived to adulthood, only one daughter, Hester, married and had children.  For Fanny and Dickey their seven children were a constant source of anxiety for the couple, with fatal accidents and bouts of mental illness. Their eldest daughter Hester married William Harwood, and it was their children who were the last private owners of the Hammond-Harwood House until 1924.

During the War of 1812 Dickey served in the militia in both Caroline County and Anne Arundel, serving a total of 81 days. It is likely he was at the Battle of Bladensburg on August 24, 1814 which was a great loss to the Americans and resulted in the burning of Washington D.C. He was not at the bombardment of Fort McHenry when the Star Spangled banner was written, but he was actively serving in the militia during this time.

In December of 1817 he was elected State Auditor of Maryland  but by 1819 there were issues, and he was suing the state for back wages.

Dickey’s main livelihood was his plantation, Bennett’s Tolson, where wheat, corn, tobacco grew in addition to having cows, hogs, sheep, and turkeys. Dickey was in a favorable neighborhood and would have associated with the Daffin’s of nearby Daffin House, an architecturally significant property, that hosted president Andrew Jackson in 1806.

Despite his prospects Dickety was thrown into immense economic struggle in the early 19th century between the war of 1812 and the panic of 1819. It was not the genteel life his father had envisioned for him.

Dickey’s father had been an active Methodist and had instituted a gradual emancipation for the eighteen enslaved people mentioned in his will. The last enslaved person to be granted freedom at Bennett’s Toulson was in 1816. During the late 18th century emancipation became a popular idea in religious communities including the Quakers, Methodists, and Episcopalians.  It is unclear what labor Dickey used on the plantation but most likely it was a mix of free and enslaved African American’s. The mother in law of Frederick Douglass, Mary Murrary, was born on this property and granted her freedom around 1813, so that her daughter Anna born in 1813 was freeborn. Anna Murray Douglass was a very talented and resourceful woman who married Frederick Douglass in 1838, and was a great source of inspiration for him. In modern day Denton on Tuckahoe Road just above the former Loockerman property there is an African American community.

Dickey Loockerman’s difficult finances affected his not only his immediate family but also the enslaved population he owned. In 1821 he mortgaged his enslaved women Juliet to a merchant tailor, Nicholas Watkins, for a year so that he could pay a debt. Watkins owned a tailor’s shop on Conduit Street in Annapolis. Juliet may have cooked, cleaned, or been trained in sewing. After the year had passed Richard refused to pay the remaining debt, however, Juliet was able to return.

Dickey divided his time between his plantation and the city house in Annapolis. In 1827 Judge Chase foreclosed on his son in law’s back payments. He was given one month to sell his eastern shore properties. The court appointed Dickey’s first cousin, Theodore Loockerman, a local lawyer, and the son of his Uncle Jacob. However, Theodore wrote,
“being closely related to one of the parties in the transaction, I feel compelled by delicacy to decline the trust.” The matter seemed to go on for years and it was still proceeding in November of 1834 when Dickey unexpectedly passed away at Bennett’s Toulson.

There are two letters (see below) that tell a very different story about the death of Dickey Loockerman. I leave it up to you to decide what fate befell Dickey.

The first is from Dickey’s cousin Theodore to Fanny Loockerman here in Annapolis:

“Procured an excellent nurse by the name of Hicks, who remained until the last moment. Every attention was rendered that could be. The room, the bed etc. were very comfortable. As far as I could ascertain his mind was calm and collected to the last. And although I was not informed of his expressing any particular wish in regard to his family he spoke frequently generally of them and expressed his desire to see them.” December 2 1834

The second letter is dated the same day December 2 1834 is written by a family friend, Mrs. Trippe to her son in New York:

“What won’t the love of strong drink do_ he came over to Caroline on business, got in a drunken frolic (sic) and continued so about 3 weeks, was taken ill among the black people, who lived on his farm and actually breathed his last in a black man’s house, thus my dear, has closed the temporary career of one of the handsomest, most sensible and well informed men of our age”

Charming, smart, attractive yet flawed the life of Dickey Loockerman is still somewhat of a mystery to us here at Hammond-Harwood House, but this trip gave a greater context into the world he lived in and the economic struggles he faced in early 19th century Maryland.




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