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Historical Sites & Landmarks

Heritage Trails  | Sites & Landmarks | Museums | UGRR | Genealogy & Historical Info


Caroline County Courthouse
Although chosen by the Maryland legislature in 1773 as the county seat, the creation of Denton was delayed until word arrived in 1781 that the British were surrendering at the Battle of Yorktown. The current Romanesque and neo-Georgian courthouse (c. 1895) replaced the original courthouse (c. 1797) that was believed to have been designed by William Buckland.
109 Market Street, Denton

Sophie Kerr House – Private home
Kerr grew up in Denton and lived much of her adult life in New York City where she was managing editor of the Woman’s Home Companion. She was educated at Hood College in Frederick and the University of Vermont. She began to write stories at 18 years of age and did newspaper work in Pittsburgh. She contributed stories to all the major magazines in the country. In her will, she bequeathed half a million dollars to Washington College in Chestertown, MD to fund one promising graduating writer each year – currently over $50,000 award annually.
608 Fifth Avenue, Denton

Colonel Richardson’s Tomb – A State Historic Marker
In 1776 Richardson’s 5th Maryland Regiment drove the British from the field at the Battle of Harlem Heights. This, the first victory of the Continental Army in a stand-up fight, restored the confidence of the previously badly-beaten American soldiers. Richardson later suppressed pro-British rebellions on the Eastern Shore before being captured and held prisoner in England until 1781. This idyllic spot was his home at Gilpin’s Point, circa 1765-1825.
Two miles north of Harmony on Route 16

Dickenson Memorial Marker – A State Historic Marker
Charles H. Dickinson was born on the adjacent farm into a family which achieved national prominence through John Dickinson, “Penman of the Revolution.” Located at Routes16 and 621 south of Harmony

Federalsburg Railroad Station – c. 1870
Following the arrival of the Pennsylvania Railroad in 1868, goods from area mills and tanyards were transported from Federalsburg by rail to larger markets in New York and Philadelphia.
Main Street and Railroad Avenue, Federalsburg

Goldsborough House
This house was home to Washington Laird Goldsborough (1897-1958). A hero at the battle of San Juan Hill in the Spanish-American War, he served as Judge Advocate of Manila, Philippine Islands.
116 W. Sunset Avenue, Greensboro

Jacob Leverton Dwelling – Private home
The Jacob Leverton Dwelling was “the main stopping place,” a focal point around which several adjoining landowners participated in a broad stronghold of Underground Railroad activity. From their early 19th century residence, Quakers Jacob and Hannah Leverton aided escapees moving under cover to freedom in the North. It is a designated site of the National Underground Railroad Network to Freedom Program, 3531 Seaman Road, Preston

Preston – A State Historic Marker
Preston was founded in 1846 around Frazier’s Chapel, an early Methodist Church. First called Snow Hill, the name was changed to Preston by an act of legislature in 1856, in honor of a prominent Baltimore lawyer.
At Main & Maple Streets, Preston

Linchester Flouring Mill Complex
One of the last water-powered mills on the Eastern Shore, it ceased operating in 1979 when the mill pond dam broke after heavy rains. The structure has been described as a “treasure of America” because its original equipment reflects the long evolution of American milling. Of special interest is the Fitz water- wheel on the south (rear) side of the mill, and the Miller’s dwelling across the road.
3390 Linchester Mill Road, Preston 410-673-1910

Mason Dixon Line – A State Historic Marker
A Crownstone of the Mason-Dixon Line is located in Marydel. The dividing line was surveyed in the 1760s by Charles Mason and Jeremiah Dixon to settle the contradictory land claims of the Penn and Calvert families. Caroline County’s eastern border was marked by 36 stones placed at one-mile intervals; while every 5 miles Crownstones were placed. 33 of the mile stones remain. Route 8, Marydel

Ridgely House – now the Ridgely Town Hall
James K. Saulsbury, a veteran of the California Gold Rush of 1849, built this property as his residence and general store. It was one of the first two private residences built in Ridgely. Dr. Jessee Fifer purchased the property and established and operated a hospital here from 1935-1945. The Ridgely House, which exemplifies the historical heritage of the Town of Ridgely is open to the
public and currently houses a collection of
early photographs and memorabilia.
Central Avenue, Ridgely

St. Paul’s Episcopal Church
This Church was established in 1748 at nearby Tuckahoe Bridge in Queen Anne’s County. A church was built at this site in 1768, but it fell into decline as the influence of Methodism grew on the Eastern Shore. Under the guidance of Rev. Robert William Goldsborough, construction of the present gothic revival structure began in1853.
Corner of Maple & Church Streets, Hillsboro