Douglass Returns


Approximate drive time is one hour.

On this tour, you will travel through some of the vast holdings of Edward Lloyd V (1779-1834), once one of the wealthiest men in Maryland. He succeeded five generations of Lloyds, whose agricultural interests were established in 1660 and steadily increased. The Lloyds were predominantly seated in the Miles River Neck area bounded by the Wye River to the north and the bending Miles River to the east, south, and west. The finger-like waterways forming the large neck of land permitted shipping of tobacco, grain, pork, beef, and timber to larger markets. The Lloyd farms were among the first to convert from tobacco to wheat, which they supplied to the Continental Army.

The locations of fields and woods are largely unchanged from 1824 when Frederick Douglass (then Frederick Bailey) arrived. The narrow roads of Miles River Neck date to the 17th century, though most travel then was by water.

PLEASE NOTE: These tours will take you on busy roads, as well as many rural back roads. Use caution when pulling off to view a site or read from the guide. Many of the buildings associated with Frederick Douglass in Talbot County are no longer standing, and their exact locations are unknown; this guide directs you to the approximate vicinity of each site. In addition, many of the sites included are private property. Please respect property owners and do not trespass or use private lanes and driveways. In Talbot County, road names with green signs are public. Roads name with blue signs are strictly private.

Self-Guided Driving Tour #2

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Driving Tour #2 - Start Here

Driving directions: Start at the intersection of Airport Road and Maryland Route 662 N/Longwoods Road. Proceed approximately 1.5 miles and turn left on Sharp Road. Proceed approximately 1.4 miles to a bend in Sharp Road and proceed straight ahead another 1.4 miles on Little Park Road. Turn left on Todds Corner Road and continue 1.15 miles. The road becomes Bruffs Island Road. Follow Bruffs Island Road, keeping right at Gregory Road. Proceed 2.6 miles to a circular turnaround which is Site #1. Turn around in the circle at the Wye Town Farm Bruffs Island sign and pause to view the landscape on either side. Site #1 text notes explain Douglass’s experience here.

Site #1 – Lands of Edward Lloyd V

Driving to Site # 1, you have passed through many of the old Lloyd farms, encompassing thousands of acres. Note the 1858 farm map below. Most of the farms are labeled Lloyd or Tilghman (a family intermarried with the Lloyds). Douglass lived on Lloyd land from 1824 to 1826.

Detail from 1858 Dilworth Map of Talbot County Farms. Source: Library of Congress.

Edward Lloyd V was a statesman as well as an agriculturalist. He served in state and federal politics throughout his life and was governor of Maryland before Douglass’s time. Lloyd was then a United States Senator from 1819-1826. His property in land and slaves constituted a giant agribusiness operating under a plantation system, which he built from 12 to 20 farms, each with an overseer.

By 1832, Lloyd owned and was taxed on 577 slaves in Talbot County, a 25% increase from 1817. Lloyd was personally involved in his farming operations but lived in Annapolis or Georgetown during legislative sessions and the social seasons. Douglass’s owner, Aaron Anthony, was Lloyd’s farm superintendent — the “overseer of overseers.” Anthony managed all of the overseers, the shipping and receiving of grain, and the on-site manufacturing necessary to run all the farms. In the spring of 1824, Douglass was summoned from his grandmother’s cabin to begin life as a slave in Anthony’s rented house at the central Great House Farm. He was six years old.

When Douglass lived in Anthony’s house on Great House Farm, he lived with Bailey kin including some siblings and aunts he met for the first time. They lived in the kitchen wing adjoining the main cottage, which housed two to five Anthony family members and 15 Anthony slaves. The household often included Lloyd’s boat captain, Thomas Auld, who was married to Anthony’s daughter Lucretia.

Photo from Historic American Buildings Survey E. H. Pickering, Photographer December 1936. Over 100 years after Douglass & Anthony were here. Kitchen wing on right.

Well over 100 of Edward Lloyd’s slaves lived on the central farm in quarters near the Anthony house, and those enslaved persons who labored on the surrounding farms would come periodically for food allowances. Thus young Douglass’s formative boyhood years were spent at the very hub of a plantation slavery system that was both busy with industry and totally isolated by family out-farms and rivers. He observed slavery’s cruel realities. He was also mindful of the beautiful natural environment and the amenities of the wealthy and politically powerful Lloyd family. He described the extremes in three autobiographies, relying on sharp boyhood memories.

The names of the farms nearest to the home plantation were Wye Town and New Design.”Wye Town” was under the overseership of a man named Noah Willis. New Design was under the overseership of a Mr. Townsend. The overseers of these, and all the rest of the farms, numbering over twenty, received advice and direction from the managers of the home plantation. This was the great business place. It was the seat of government for the whole twenty farms. All disputes among the overseers were settled here. If a slave was convicted of any high misdemeanor, became unmanageable, or evinced a determination to run away, he was brought immediately here, severely whipped, put on board the sloop, carried to Baltimore, and sold to Austin Woolfolk, or some other slave-trader, as a warning to the slaves remaining. — Frederick Douglass, Life and Times of Frederick Douglass

Site #1 is located between Miles River and Shaw Bay on the Wye River. Shaw Bay’s deep water anchorage still attracts sailing vessels and would have harbored the Sallie Lloyd, a state-of-the-art, luxuriously appointed sailing sloop commanded by Captain Thomas Auld, Aaron Anthony’s son-in-law.

courtesy Spocott Windmill

You are at the nexus of Wye Town Farm and Great House Farm, where a windmill served as a source of fascination to the young Douglass. The symbols of freedom and self-power in the sails of the vessel and the sails of the windmill’s wings recur throughout Douglass’s autobiographies.

The little tendrils of affection, so rudely broken from the darling objects in and around my grandmother’s home, gradually began to extend and twine themselves around the new surroundings. Here, for the first time, I saw a large windmill, with its wide-sweeping white wings, a commanding object to a child’s eye. This was situated on what was called Long Point–a tract of land dividing Miles river from the Wye. I spent many hours here watching the wings of this wondrous mill. In the river, or what was called the “Swash,” at a short distance from the shore, quietly lying at anchor, with her small row boat dancing at her stern, was a large sloop, the Sally Lloyd, called by that name in honor of the favorite daughter of the Colonel. These two objects, the sloop and mill, awakened as I remember, thoughts, ideas, and wondering.
— My Bondage and My Freedom.

As you proceed towards site #2, all the farmland and woods on both sides of the road are part of Wye Town, Great House, and New Design Farms observe the historic gates of the Great House Farm lane on your left as you pass.

Please Note: Now known as Wye House, Great House Farm is a private residence. Do not enter the driveway, farm lanes or private roads. The current owners will consider written requests for tours submitted by educational or charitable organizations. Requests may be submitted to the Talbot County Department of Economic Development and Tourism. Under no circumstances will requests from commercial tour operators be granted.

The current owners have contributed greatly to the history of American slavery by supporting nine years of archaeological investigation conducted by the Department of Anthropology of the University of Maryland at College Park. You can view rich online exhibits, including a searchable database of the enslaved people who lived on the property compiled from early Lloyd records.

Site #2 – Copperville (formerly Village of Liberty) and Deshields Cemetery

Use caution here. Roads are narrow, and there are few places to pull over.

Copperville is a small, historically significant African-American village located near one of the few Miles River Neck farms not owned by Edward Lloyd: the Andrew Skinner Farm now known as Fairview. Frederick Douglass’s Bailey family ancestors lived at the Skinner Farm from the mid-17th century. When Ann Skinner married Aaron Anthony in 1797, Douglass’s grandmother Betsy Bailey was one of Ann’s slaves and was moved from the Skinner farm to Anthony’s farm at Tuckahoe.

After emancipation in Maryland, freed slaves of the Lloyd and Skinner families purchased lots and settled Copperville. It was then known as the village of Liberty. Note that the cemetery lies between 4th Lane and Bailey Lane. The first lots were purchased by Civil War veterans Solomon Deshields and John Copper in 1867, and several dozen more lots were purchased over the following decades, including the lot bought by the Trustees of the Asbury Church at Miles River Neck (later Deshields United Methodist Church).

Artist Ruth Starr Rose, who lived on a nearby farm, painted members of the Copperville community and scenes of the spiritual life of the church. Recent exhibitions of her work at the Reginald Lewis Museum in Baltimore and the Easton Armory depict life in Copperville with a dignity and respect rarely seen in the segregated era of the first half of the 20th century. The church cornerstone dates the building, which has recently been converted into a private home, to 1895.

Driving Notes: Continue on Copperville Road and turn left at Tunis Mills Road. At the intersection, note Fairview Point Lane which was the Skinner Farm, birthplace of Douglass’s  grandmother, and Voit Road which was the home of Ruth Starr Rose. Continue over the bridge at Leeds Creek into Tunis Mills, a late 19th century mill town. At Leeds Landing Road, bear left to continue on Tunis Mills Road.

The Oakland or Tunis Mill was located on land purchased from Lloyd. A number of residents of Copperville and Unionville found employment at the mill after the Civil War. Tunis Mills also had two stores that served Copperville residents.

Site #3 – Unionville at St. Stephens A.M.E. Church (9467 Unionville Rd)

Driving Notes: From Tunis Mills Road, turn right on Unionville Road (Rt. 370); continue through the village of Unionville to the church on the left.

Our Douglass tour intersects here with the Civil War Trail. The village of Unionville was settled after the Civil War by emancipated slaves from the Lloyd plantations and by free persons who had worked for Ezekiel Cowgill (pronounced KOH-gul). Cowgill was a Quaker abolitionist who came to the area from Delaware in 1856 and bought a large farm, Lombardy, adjoining Edward Lloyd on the upper Miles River.

After the Civil War, returning Union Army veterans of the United State Colored Troops (U.S.C.T.) purchased town-sized lots from Cowgill, who believed in community development and profited over time through a unique financing arrangement. Terms were $1 per month for 30 years, with free access to timber for fencing and house-raising. As an interest free, rent-to-own deal, the purchase terms benefited both parties. Cowgill also sold lots outright at $1 per lot for a church and a school. Community trustees agreed to raise the buildings.

The church and the school formed the heart of Unionville’s progressive community; there were also fellowship halls. When the first schoolhouse burned, it was replaced in 1932 by a school relocated from McDaniel. The McDaniel school was started in 1821 by prominent shipbuilder Thomas Kemp; located on the Bayside road, Douglass walked past it many times during his teenage years (Tour #4). Sadly, the second Unionville schoolhouse also was burned in recent years. St. Stephens A.M.E. Church remains the active center of Unionville today.

School on Route to Unionville: The Easton Star Democrat July 3, 1936

A historic marker at the church honors the 18 Union Soldiers who returned to build homes and create their town on land worked by their ancestors for generations. U.S.C.T. markers designate their graves in the burial ground behind the church. Cowgill’s son John broke from his father’s pacifist religious beliefs and served as captain of Company A of the 108th Regiment of United States Colored Infantry.

After the war, in 1867, John Cowgill returned to Lombardy and led the local volunteers of the 1st Eastern Shore Colored Militia in their drills. When some of the southern-sympathizing Talbot County whites excoriated him in the local press, African American leaders from the militia wrote a letter to the Easton Gazette in his defense. Unionville is a testament to the power of liberty, place, and kinship ties. Many collateral descendants of Frederick Douglass’s family live today in Unionville and Copperville.

Driving Note: Follow Unionville Road South. At the Miles River Bridge, note that properties on both sides of the Miles River were large farms owned by daughters of Edward Lloyd V. On the south side, an historical marker designates The Rest, home of Ann Catherine “Nannie” Lloyd, wife of confederate admiral Franklin Buchanan. Douglass visited her at The Rest in 1881.

Proceed to the intersection of Unionville Road and Maryland Route 33/St. Michaels Road. Tour 2 end here. Turn left to return to Easton. Turn right to continue to St. Michaels and begin Tour 3.

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