Talbot County Timeline

Frederick Douglass was one of the most consequential figures of nineteenth century America. Born into slavery in Talbot County, Maryland, he shook off his bondage when he was twenty and became an internationally recognized abolitionist, philosopher, editor, and best-selling author whose works were translated into several languages. An intellectual force, his powerful oratory calling for emancipation, equality, and universal suffrage shook the world with messages that remain vibrant and timely today.  

The following timeline provides key dates regarding his Talbot County experiences that were part of his life journey.

February 1818


Born Frederick Augustus Washington Bailey at Holme Hill Farm along Tuckahoe Creek in Talbot County; lives with his grandmother, Betsey Bailey, on the farm until he is six.

August 1824

age 6

Taken by his grandmother Betsey to live on the Lloyd Plantation at Wye House along the Wye River at the home of his slaveholder, Aaron Anthony.

February 1825

age 7

Visited by his mother, Harriet Bailey, for the last time before her death. She could only see him at night after the day’s work was done and had to return by sunrise, walking up to two dozen miles over roads only lit by moonlight.

March 1826

age 8

Sent to live with Hugh and Sophia Auld in Fells Point, Baltimore. Among other things, Sophia begins teaching Frederick to read.

November 1826

age 8

Aaron Anthony dies without a will.

October 1827

age 9

Called back to Holme Hill Farm for the division of Anthony's property, travels by boat down Chesapeake Bay and up the Choptank River. Awarded in the division to Thomas Auld who becomes his new slaveholder and returns him to his brother Hugh Auld in Baltimore.

March 1833

age 15

Following quarrel between Hugh and Thomas Auld, sent to St. Michaels where Thomas is a storekeeper and postmaster. Travels from Baltimore to St. Michaels aboard the sloop Amanda, lives at Thomas Auld's residence on Cherry Street in St. Michaels for the remainder of the year.

January 1834

age 15

Rented out to Edward Covey as a field hand on his farm overlooking the Chesapeake Bay below Wades Point, seven miles from St. Michaels. Douglass describes his new servitude, “like a wild young working animal, I am to be broken to the yoke of a bitter and life-long bondage.”

August 1834

age 16

Because of “the savage persecution to which I had been subjected,” Douglass fights to a draw with Covey on Covey's farm, “the turning point in my ‘life as a slave.’”

December 1834

age 16

Returns to Thomas Auld's residence in St. Michaels when term with Covey ends on Christmas Day.

January 1835

age 16

Rented out to William Freeland whose farm is two miles north of St. Michaels.

April 1836

Age 17

Formulated plans to shake off his bondage by using a log canoe which would “bear me into freedom;” arrested when plans discovered; jailed in Easton, released into custody of Thomas Auld who sent him back to Hugh Auld in Baltimore.

September 1838

age 20

While living in Baltimore, escapes to New York City dressed as a sailor on leave where he is joined by Anna Murray who he marries, changes his name to Frederick Douglass and continues journey to New Bedford, MA.

December 1846

Age 28

After ownership of Douglass had been transferred to Hugh Auld by Thomas Auld, freedom is purchased while in Great Britain after friends there raise L150 ($712).

June 1877

age 59

Visits St. Michaels with residents lining the streets, meets with Thomas Auld in a tearful reconciliation, gives a speech on the town green.

November 1878

Age 60

Visits Easton, dedicates Asbury United Methodist Church, addresses Bethel AME Church, travels to his birthplace along Tuckahoe Creek going through Tappers Corner.

March 1881

age 63

Returns for a visit to Wye House on the Lloyd Plantation.

March 1893

age 75

Returns to Talbot County visiting St. Michaels and Easton, offered places to purchase in the area including The Villa near Easton and Perry Cabin Farm in St. Michaels. Inquires about purchasing Sharon, a 200-acre farm where Thomas Auld had lived in his later years but declines an offer by an Auld heir to tour it. No purchases of property by Douglass in Talbot County were ever made.

February 1895

age 76

Dies of a heart attack at his home Cedar Hill in Anacostia in Washington, DC.