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Where Did Frederick Douglass Land in Talbot County When He Returned for the Division?

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In November of 1826 when Frederick Douglass was eight years old, he was living with the family of Hugh and Sophia Auld in Fells Point when his slaveholder, Aaron Anthony, died without a will in Talbot County, Maryland. Under Maryland law, Anthony’s property was required to be divided equally among his heirs. As an enslaved person, Douglass was considered part of Anthony’s property and therefore was subject to evaluation and division. 

The following October, Frederick was called back to Holme Hill, Aaron Anthony’s farm in Talbot County, for the process of evaluation and division of all Anthony’s property under the supervision of the County’s Orphan’s Court.

We have clear records that Frederick Douglass returned to Talbot County for the division, but precisely where he landed when he arrived on the Shore is murky. This post describes the various places that Douglass may have stepped off the boat transporting him from Fells Point. It provides perspectives based on what Douglass’s biographers have said plus those of members of our editorial board who have spent considerable time boating on the Choptank River and Tuckahoe Creek. We have conducted this research because the photographic essay that Jeff McGuiness is working on would like to be as accurate on this point as possible.

In his autobiography Narrative of the Life of Frederick Douglass: An American Slave, Douglass said that he took passage with Captain Rowe in the schooner Wild Cat and that he arrived “near the place of my birth.” Specifically,

I took passage with Captain Rowe, in the schooner Wild Cat, and, after a sail of about twenty-four hours, I found myself near the place of my birth.

There is no mention of the details of this journey in either of his other two autobiographies, My Bondage and My Freedom and Life and Times of Frederick Douglass.

In Dickson Preston’s biography of Frederick Douglass, Young Frederick Douglass, the former news reporter discusses this trip in more detail. He writes:

The trip by schooner took twenty-four hours; Wildcat was a slow tub of a boat, stubby and broad of beam with shallow draft and a centerboard rather than a keel, so that she could creep up the Eastern Shore’s many tidal creeks. Frederick spent much of the time brooding, or dozing on tarpaulins piled on the open deck. When he awoke next morning, the schooner was far up the Choptank, near the mouth of Tuckahoe Creek and the old Anthony farm where his fate would be decided.

No citation is given for these additional details. Also, Wild Cat in Narrative becomes Wildcat in the Preston biography, a change that is mirrored in other Douglass biographies and writings. And some have said the boat transporting him sailed up the Tuckahoe.

So where precisely did Douglass land?

A trip by boat under sail alone can bring a watercraft from Baltimore up the Choptank to Easton Point on the Tred Avon River within twenty-four hours. From there Douglass could have walked the 13 miles to Holme Hill Farm or hitched a ride there. With the tide running hard up the Choptank River, a sailing craft can also reach Kingston Landing within 24 hours if all the elements are in alignment. From there, the walk to the farm is only 9 miles. 

Could the boat transporting Douglass have gone up the Choptank, then up Tuckahoe Creek to Holme Hill Farm? Yes, but not without difficulty and considerable consumption of time. It would have been quicker to simply walk from Kingston Landing to Holme Hill. Tuckahoe Creek is a narrow waterway with a strong tidal current that winds its way between forested banks for several miles. Steamships did make stops along Tuckahoe ports later in the nineteenth century, but such a journey by sailboat would have been a struggle with the constant twists and turns the creek makes. Nevertheless, if the watercraft was owned by the Lloyd family and was servicing agricultural operations along the Tuckahoe owned by the Lloyds or people with whom they were doing business, then it likely the boat had no choice but to work its way up that creek. Further, Douglass may have reached the Kingston Landing area in 24 hours as he said he did and then spent the rest of the day riding the tide up the Tuckahoe with the Wild Cat takig advantage of favorable winds when they became available.

We posed these questions to Bronwen Masemann of Masemann Research, and her findings can be found at this link.

Her conclusion was that “sail-powered vessels made regular cargo and passenger runs between Baltimore, Annapolis, and ports along the Choptank River in the 1820s." By going through local newspapers printed during the 1820s, she found advertisements for a schooner called Jane and Mary that did a weekly run between Easton Point on the Tred Avon River off the Choptank and Baltimore. The Jane and Mary was described in these advertisements as a “REGULAR PACKET & GRAIN BOAT.” The schooner was commanded by Captain Thomas Roe. Roe is a far more common name in Talbot County than Rowe.

Ms. Masemann found no record of a commercial boat doing a regular run up the Choptank beyond the Tred Avon River, though it would seem commercial transportation must have been available from Baltimore to Cambridge, Maryland, by then. And perhaps there were regular runs of boats transporting grain from farms along the Choptank as far upriver as Denton, ones that were not advertised and did not carry commercial passengers, and perhaps Douglass was on one of those watercraft. The Lloyd name comes up prominently in geographic names in the area of Talbot County fronting the Choptank, and with the Lloyd family’s extensive agricultural holdings, the Lloyds did own their own means of transportation for their crops as described in Douglass’s autobiographies. Still, these would likely have not been captained by the Capt. Roe Ms. Masemann found.

Ms. Massemann also researched the boat’s name of Wild Cat or Wildcat and found that it was a common boat name in use at that time. However, she found no reference to a commercial craft called Wild Cat or Wildcat on the Bay during the early nineteenth century. Again, Wild Cat or Wildcat could have been owned by the Lloyd enterprises.

In sum, it is anyone’s guess where Douglass stepped off the boat.

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