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Caroline County Markers
Maryland (Caroline County), Andersontown — North-South Boundary Between the State of Maryland and the State of Delaware
This monument commemorates the completion in 1976 of the resurvey by the U.S. Department of Commerce of the north-south boundary between the State of Maryland and the State of Delaware known historically as the Mason and Dixon Line. The original limestone markers, some of which bear the armorial shields of the Calvert (Lord Baltimore) and Penn families, were established by the original survey made by Charles Mason and Jeremiah Dixon in 1764. — Map (db m88751) HM
Maryland (Caroline County), Denton — Caroline Court House
Caroline County-established, 1773, from parts of Queen Anne's and Dorchester Counties - held its early courts at seven different locations until 1797 when its first courthouse was built on this site, once known as Pig Point. The 1895 replacement was renovated and extensively added to, 1966. The courthouse was purchased 1791 for 120 shillings. — Map (db m3388) HM
Maryland (Caroline County), Denton — Caroline Courthouse-In the Shadow of JusticeHarriet Tubman Underground Railroad Byway
Many facets of 19th century rural life focused on a county’s courthouse. Elected officials, lawyers, merchants, and ordinary citizens all had reasons to gather at the Caroline County Courthouse Square. For the enslaved and abolitionists, the square possessed a more sinister purpose.

Conducted in the shadow of the courthouse—the symbolic center of government and justice—local slave auction exhibited the inhumanity and raw, lucrative economics of the antebellum slave trade. The . . . — Map (db m79340) HM

Maryland (Caroline County), Denton — Choptank River Heritage Center-Steal Away by RiverHarriet Tubman Underground Railroad Byway
The Choptank River was as entwined with the history of slavery and freedom on the Eastern Shore as any plantation. Slaves arrived by boat for auction and left the dock in the hands of a new owner. At wharves like this, black watermen played an important role in freedom’s network, bringing news, passing gossip, and occasionally whispering advice about the prospects for escape.

A river crossing was always dangerous for fleeing slaves. Few could swim, and currents were strong. Bridges were . . . — Map (db m79342) HM

Maryland (Caroline County), Denton — Denton
Originally called "Edenton" for Robert Eden, Maryland's last Colonial Governor. CAROLINE COUNTY was named in honor of his wife Caroline Calvert, a sister of Frederick, the last Lord Baltimore. — Map (db m3391) HM
Maryland (Caroline County), Denton — Great Wars of World Conflict
Dedicated in honor of the men and women from Caroline County who served their country during the great wars of world conflict. — Map (db m4534) WM
Maryland (Caroline County), Denton — Hubs of ActivityTerminals, Wharves and Landings on the Choptank
Sailboats and steamboats unloaded and loaded passengers and freight all along the Choptank. As trade increased in the 1800s, people built wharves and landings every few miles on the river. A wharf bustled with activity when a boat arrived. Children raced to the dock to watch the action. Stevedores moved freight. Passengers disembarked or boarded. Farmers brought their products to the dock for loading. Locals exchanged news with travelers. The steamboat terminal at West Denton, owned . . . — Map (db m68427) HM
Maryland (Caroline County), Denton — John Wilkes BoothEscape of an Assassin — War on the Chesapeake Bay
Divided loyalties and ironies tore at Marylander’s hearts throughout the Civil War: enslaved African-Americans and free United States Colored Troops; spies and smugglers; civilians imprisoned without trial to protect freedom; neighbors and families at odds in Maryland and faraway battlefields. From the Eastern Shore to the suburbs of Washington, eastern Maryland endured those strains of civil war in ways difficult to imagine today. Those strains continued even after Confederate General . . . — Map (db m3390) HM
Maryland (Caroline County), Denton — Moses and the HoundsHarriet Tubman Underground Railroad Byway
Growing up as a slave near Easton, MD, Moses Viney often heard, “The wild geese come from Canada, where all are free.“ When he was 23 years old, Moses learned he might be sold to a new owner in the Deep South. To avoid this fate, he and two friends escaped on Easter morning in April 1840. They swore they would make it to Canada or die trying.

Upon reaching the Choptank River, the trio attempted to cross a bridge near here. But the plantation’s hounds were hot on their trail, . . . — Map (db m79341) HM

Maryland (Caroline County), Denton — Neck Meeting House
Neck or Tuckahoe Neck Meeting House was built in 1802 by members of the Society of Friends who had been Nicholites, a sect that originated in Caroline County. The building was used as a house of worship and as a Friends School until 1897. The building was then rented by "Dunkards" for religious meetings for black persons and as a school. It was privately sold in 1901 and since 1949 has been owned by Choptank Electric Cooperative, Inc. — Map (db m5075) HM
Maryland (Caroline County), Denton — Nest of TraitorsThe Denton Arrests
On August 17, 1862, the steamboat Balloon arrived at Denton wharf and disembarked a company of New York infantry and a troop of cavalry. The soldiers quickly arrested twelve prominent local citizens and transported them to imprisonment at Fort McHenry in Baltimore. Had the U.S. Army broken up a nest of traitors as implied by pro-Union newspapers, or was this an example of what states-rights poet James Ryder Randell described as the "despot's heel" in rural Maryland? Clearly, . . . — Map (db m68428) HM
Maryland (Caroline County), Denton — On this spot Sept. 5, 1938 stood Franklin Delano Roosevelt
"It is the privilege of some of us to dream dreams, and some of us to carry out the dreams of others" — Map (db m3541) HM
Maryland (Caroline County), Denton — Revolution or Fraud?Emancipation in Caroline Co.
Maryland slaves were not freed by the Emancipation Proclamation of 1863, which excluded states that remained in the Union from its provisions. It was Maryland's new constitution, adopted by the narrow margin of 291 votes of almost 60,000 cast on November 2, 1864, that ended slavery in the state. The voluntary abolition of slavery here boosted the reelection campaign of President Abraham Lincoln. Though hailed as "The Mighty Revolution," emancipation and the new constitution resulted from . . . — Map (db m3389) HM
Maryland (Caroline County), Denton — Steamboats on the Choptank RiverConnecting Denton to the World
Steamboats carrying passengers and freight brought prosperity to Denton and Caroline County during the late 1800s and early 1900s. Caroline County's economy was based on agriculture. Farmers had to market their products. Steamboats quickly and efficiently carried fresh and canned vegetables and fruit to the Chesapeake Bay and on to markets in Baltimore and elsewhere. Farmers prospered. Canneries, granaries, a flourmill, fertilizer warehouses, a shirt factory, stores and a blacksmith . . . — Map (db m68429) HM
Maryland (Caroline County), Denton — Tuckahoe Neck Meeting House-Living Their BeliefsHarriet Tubman Underground Railroad Byway
The Quakers, also known as Friends, who met in this Meeting House not only held strong opinions on the abolition of slavery and women’s rights, but they also acted on those beliefs.

After 1790, the Friends who gathered here refused membership to slaveholders. They also played critical roles in the Underground Railroad, relying on family, friends, and business contacts in the North to move fugitives from one safe house to another along the many paths to freedom.

For many 19th century . . . — Map (db m79354) HM

Maryland (Caroline County), Denton — William Still Center-Families Divided & UnitedHarriet Tubman Underground Railroad Byway
William Still’s mother Sidney and several of his siblings lived in a cottage on the plantation where they were enslaved. Sidney escaped with her children to join her husband in New Jersey, but she was soon recaptured and returned to Maryland. Leaving her two boys behind but taking her two daughters, she fled again, this time successfully. As punishment, her angry owner sold her sons Peter and Levin.

Sidney gave birth to her last child, William, in freedom in New Jersey. As an adult living . . . — Map (db m79313) HM

Maryland (Caroline County), Federalsburg — Marshyhope Creek Bridge
Until it was named Federalsburg in 1812, the community took its name from the bridge at this crossing. This 215-foot concrete structure was built in 1910 by the Luten Bridge Company of York, Pennsylvania, a firm noted for its filled Spanderel Arch design. It was built as part of the newly-formed state roads commission's plan to improve the highway system. Repaired and altered after the flood of 1935. — Map (db m60467) HM
Maryland (Caroline County), Greensboro — Goldsborough House
Judge Laird Goldsborough lived here 1897-1970. As onetime Adjutant General of the Philippines he authored the Island's first constitution. Part of the house is of pre-revolutionary construction. Among other members of this Caroline County family distinguished for public service: W. E. Goldsborough, U. S. Consul, Amoy, China; T. Alan Goldsborough, longtime U. S. Congressman and Federal Judge; Dr. G. Winder Goldsborough, General Practitioner and State Legislator; and Elwell Goldsborough nationally famous electrical engineer. — Map (db m3394) HM
Maryland (Caroline County), Greensboro — Greensboro
Founded 1732 as Bridge-Town, then in Queen Anne's and Dorchester Counties. Named Greensboro 1791. Sessions of Caroline County Court held here November, December, 1778; June 1779; march, 1780. Choptank Bridge, the first across the river built near here before 1732. — Map (db m3395) HM
Maryland (Caroline County), Greensboro — Greensboro-Threatened by IdeasHarriet Tubman Underground Railroad Byway
More than cargo flowed through commercial towns like Greensboro. Abolitionist ideas and freedom seekers on the move created tension within a society dependent on slavery.

Site of the northern-most bridge over the Choptank River, Greensboro served as a link between the river and overland traffic. Dockworkers loaded and unloaded grains, timber, and manufacturing goods. Transferred to wagons, cargoes lumbered along to markets in Delaware, Philadelphia, and beyond. In return, news and ideas . . . — Map (db m79356) HM

Maryland (Caroline County), Greensboro — Letter to LincolnChaos on the Eastern Shore
The war divided communities in Maryland, pitting neighbor against neighbor. During Confederate Gen. Robert E. Lee's first invasion of the North, which ended at Antietam, a Greensboro resident wrote to President Abraham Lincoln for assistance on September 13 1862: We the Loyal Union people of the Eastern Shore of Maryland are in contact constantly with vile secesh(secessionists) Traitors, that frequently threaten us with vengeance when Stonewall Jackson comes into the state. They declare . . . — Map (db m3398) HM
Maryland (Caroline County), Greensboro — Peter HarringtonRevolutionary Officer, founder of Greensboro
Son of Nathan Harrington and grandson of Peter Rich, early landowners here. He served in 1778 as 2nd Lieutenant, 28th Battalion of Militia, Caroline County. In 1783, he successfully laid out town on tract called Ingram's Desire (efforts to sell lots beside Choptank Bridge in 1732 having failed). He built brick house, church and Bernard Avenues, 1786-1789. After his death in 1814, he was buried in this yard which he had donated for Methodist Meeting House in 1789. Nearby are graves of his younger son Alexander and daughter Mary. — Map (db m3396) HM
Maryland (Caroline County), Harmony — “Sailing Away to Freedom”-Glipin PointHarriet Tubman Underground Railroad Byway
Glipin’s Point was one of the busiest wharves along the Choptank River in Caroline County where steamboats and sailing vessels transported people, timber, agricultural products, and seafood. It sat just upriver from Dr. Anthony C. Thompson’s plantation where Harriet Tubman’s parents lived and where Tubman herself conducted several of her most famous escapes.

Forty-year-old Joseph Cornish, a blacksmith and minister, was enslaved by Capt. Samuel W. LeCompte, USN, who worked him very hard. . . . — Map (db m79311) HM

Maryland (Caroline County), Harmony — William Richardson
Tomb of William Richardson Patriot Col. of the Flying Camp of the Maryland Line Hero of battles of Long Island and Harlem Heights 1776 — Map (db m79312) HM
Maryland (Caroline County), Hillsboro — Frederick DouglassTales of Horror
The anti-slavery movement was a major factor in the regional contention that led to the Civil War. During the 1840s and 1850s, no individual generated greater support in both America and Europe for that movement than Frederick Douglass. His eloquent speeches and writings were uniquely influential because they were based on his personal experiences as a Maryland slave from his birth near Hillsboro in 1818 until his escape from Baltimore in 1838. Many of Douglass' best known and most . . . — Map (db m68430) HM
Maryland (Caroline County), Hillsboro — St. Paul’s Episcopal Church(St. John’s Parish)
Established 1748 at nearby Tuckahoe Bridge in Queen Anne's County. Congregation built church here in 1768, but it fell into decline as influence of Methodism grew on Eastern Shore. Under guidance of Rev. Robert William Goldsborough, present Gothic revival structure was begun 1853, patterned after design of Richard Upjohn. Despite destructive windstorm, church was completed, consecrated in 1858. — Map (db m3393) HM
Maryland (Caroline County), Marydel — This Sapling ...
This sapling from the over 400 year old oak tree (Quercus alba) at Wye Mills, MD Planted April 1976 — Map (db m73856) HM
Maryland (Caroline County), Preston — Charles Dickenson
Born here on Wiltshire Manor in Caroline County in 1780. Moved to Foxley Hall, Easton on 1795. He read law under Judge Marshall. He met Andrew Jackson traveling across the Eastern Shore to the United States congress. He moved to Nashville Tennessee. Killed by Jackson in a duel May 30, 1806 in the Red River Valley of Kentucky. Body returned here by Truxton faithful Negro servant. Lead casket found 500 yards east of this spot Dec. 1, 1965. — Map (db m46119) HM
Maryland (Caroline County), Preston — Choptank
Before 1679, Indians had a settlement here. Present village stands on parts of tracts once known as Paradise, Belmont, Huntington and Gore. Community was "Leonard's Wharf" c. 1855 and "Medford's Wharf" later. In 1883 Choptank Post Office was established, named for both the Indian Tribe and the River. Shipping and industry spurred growth during the 1880's. — Map (db m3375) HM
Maryland (Caroline County), Preston — Choptank Landing-Escape from Poplar NeckHarriet Tubman Underground Railroad Byway
While the Choptank River could pose a troublesome barrier to those without a boat, others used the river as a path to freedom.

Josiah Bailey, an enslaved logger and shipbuilder, rowed six miles up the river. His destination was Poplar Neck, where he alerted Harriet Tubman’s father, Ben Ross, that he wanted her help to escape.

In November 1856, Harriet arrived to lead Bailey, his brother Bill, and friends Peter Pennington and Eliza Manokey to Canada. Hotly pursued, Bailey made good his . . . — Map (db m79172) HM

Maryland (Caroline County), Preston — Colonel William RichardsonBorn 1735, died 1825
Member Maryland Assembly 1773–76. Introduced bill forming Caroline County 1774 of which he was one of the Commissioners. Colonel of the “Flying Camp” of the Eastern Shore 1776. Fought at Harlem Heights. First Colonel 5th Maryland Regiment. Moved Continental Treasury from Philadelphia to Baltimore 1777. Helped suppress Tory rebellions in lower Eastern Shore. Presidential Elector 1789–1793. Lived and lies buried at Gilpin’s Point. — Map (db m3377) HM
Maryland (Caroline County), Preston — Escape from Poplar NeckHarriet Tubman Underground Railroad Byway
Harriet Tubman’s parents, Rit and Ben Ross, moved to Poplar Neck in 1847. Her father worked as a lumber foreman on Dr. Anthony C. Thompson’s 2,200 heavily forested acres. Harriet probably made her first escape from this place in 1849, and she covertly led her brothers to freedom from here on Christmas Day in 1854.

Harriet Tubman’s parents were Underground Railroad agents. In 1857, they were suspected of aiding a group of escaped slaves, known as the Dover Eight. Fearing her parents’ . . . — Map (db m79173) HM

Maryland (Caroline County), Preston — Leverton House-Finding Safe HavenHarriet Tubman Underground Railroad Byway
Refugees from slavery came here for temporary sanctuary.

Under the cover of darkness, they crept across these fields toward the home of Quaker Jacob and Hannah Leverton. The house, a rare, documented Underground Railroad station, still stands at the end of this driveway. All along the many paths to freedom, “agents” like the Levertons provided food, clothing, comfort, and transportation.

This safe house anchored a refuge that also included the homes of the free black . . . — Map (db m79303) HM

Maryland (Caroline County), Preston — LinchesterCirca 1681
Since the establishment of Hunting Creek Grist Mill prior to 1681, a mill on this site has served farmers. Known during the Revolutionary War as Murray’s Mill, it supplied provisions to the Continental Army. Linchester also was a Colonial Port of Entry. — Map (db m3366) HM
Maryland (Caroline County), Preston — Linchester Mill
Linchester Mill borders Hunting Creek, a tributary of the Choptank River flowing into the Chesapeake Bay. This historic site provided a crossing for Native Americans who traveled the Choptank Indian Trail; colonists en route to the first Choptank River ferry located at Hog Island; the first “salt raid” of the American Revolution; the first trans-Peninsula railroad to Ocean City; and for customers buying moonshine at Tom’s Still.

A mill has been here for 250 years. The . . . — Map (db m79301) HM

Maryland (Caroline County), Preston — Linchester Mill-Living DangerouslyHarriet Tubman Underground Railroad Byway
Daily life at and around Linchester Mill provided fertile yet dangerous ground for those seeking freedom.

The mill, a general store, post office and homes at this site brought whites and blacks, free and enslaved, into regular contact. Freedom and slavery existed side-by-side in stark contrast. Quakers and free blacks who lived near the mill secretly helped freedom seekers pass through the area. The mill’s dam provided a spot to cross Hunting Creek.

Underground Railroad agent Daniel . . . — Map (db m79299) HM

Maryland (Caroline County), Preston — Mt. Pleasant Cemetery-Dangerous RendezvousHarriet Tubman Underground Railroad Byway
After Quakers sold their meetinghouse to the local black community in 1849, the new owners established Mt. Pleasant Methodist Episcopal Church. The original church building has since burned, but the modern day congregation still uses the cemetery.

Laws restricted blacks from meeting in groups and a group of slaves gathering in a home or in the woods might arouse suspicion. But they did gather at cemeteries---a rare respite amidst the constant oversight that prevailed in the 19th century . . . — Map (db m79178) HM

Maryland (Caroline County), Preston — Preston
Started 1846 around Frazier's Chapel, an early Methodist Church, the land for which was purchased 1797. First called "Snowhill", the name was changed to Preston 1856, in honor of a prominent Baltimore lawyer. Preston was chartered as a town 1892. — Map (db m3365) HM
Maryland (Caroline County), Preston — Site of Frazier’s ChapelPreston, Maryland, 1785
Built by Rev. Freeborn Garrettson and Captain William Frazier. Early Methodist pastors included Jesse Lee, Joseph Everette and Bishops Francis Asbury and John Emory. Remodeled and named Bethesda 1849. Present church built 1875. Rebuilt 1958. — Map (db m3362) HM
Maryland (Caroline County), Preston — The Maryland Lot
Left panel Est 1865 The Maryland Lot owned by Maryland Steamboat Co. The beginning of Choptank Village.

Right panel In memory of the Steamboat Captains of the Chesapeake who were vital in building Choptank Village in the 1880's — Map (db m79174) HM

Maryland (Caroline County), Preston — The Underground RailroadSeed of War
Among the factors that contributed to the coming of the Civil War was the increasing animosity between Southerners and Northerners over the issue of slavery. The operation of the Underground Railroad to help slaves escape to the free North and Canada, which was supported by Northern anti-slavery societies, was a sharp thorn in the sides of slaveholders. Two major "stations" on the Underground Railroad were located near Preston. Local Quakers, long opposed to slavery, operated one and . . . — Map (db m5411) HM
Maryland (Caroline County), Preston — Webb Cabin-Living FreeHarriet Tubman Underground Railroad Byway
Common in the mid-19th century, this cabin is a rare survivor today. James H. and Mary Ann Webb built this one-room house in the 1850s, using materials found in the surrounding landscape. Hand-hewn log walls rest on a foundation of ballast stones from ships that plied the Chesapeake Bay. The interior has fireplace, a root cellar, and a loft. It is typical of homes occupied by both free and enslaved blacks, including Harriet Tubman’s parents, Ben and Rit Ross, who lived nearby at Poplar . . . — Map (db m79305) HM
Maryland (Caroline County), Ridgely — Adkins Arboretum-Slavery ArboretumHarriet Tubman Underground Railroad Byway
The forests and waterways of the Eastern Shore, traditional land of the Choptank and Nanticoke Indians, provided the backup for the austere home life, backbreaking labor, and dramatic escapes of enslaved blacks.

Hundreds of acres of white oak, black walnut, poplar, hickory and sweet gum trees, located near river transportation provided income to local landowners. Harriet Tubman and her father Ben Ross not only graded and harvested timber, but Harriet also learned lessons for living off the . . . — Map (db m79355) HM

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