The Sassafras River Water Trail
From the headwaters near the Route 301 Bridge to the river's mouth between Grove Point and Howell Point, the Sassafras River Water Trail winds past forested shorelines, bucolic farms, and high sandy cliffs for . . . — — Map (db m167808) HM
On Ericsson Avenue, 0.1 miles Main Street, on the right when traveling west.
In 1715 Edward Crew leased Fish Hall (Fishall Pattent 1664) for 11 years at the yearly rate of one ear of corn. Crew purchased 60 of the original 225 acres for 3000 lbs. of tobacco in 1726 and the remaining 165 acres in 1728. Fish Hall later became . . . — — Map (db m167078) HM
Establishing a county government is the first step for people building a stable community and a strong trade economy.
The first Kent County Courthouse was located at New Yarmouth, a 17th-century settlement abandoned when county lines were . . . — — Map (db m186650) HM
When four British barges entered Worton Creek in July 1814, local militia sprang into action. They ambushed the barges and forced them out of the creek. The Americans claimed they killed about 15 of the 20 enemy soldiers without losing any of their . . . — — Map (db m80623) HM
Kent County braced for the return of the British in August 1814. Enemy raiders had destroyed nearby Georgetown the previous year while terrorizing Maryland's Eastern Shore. Now they were back in an attempt to divert attention from their main . . . — — Map (db m186648) HM
During the Civil War, Baltimore and its environs exemplified the divided loyalties of Maryland’s residents. The city had commercial ties to the South as well as the North, and its secessionist sympathies erupted in violence on April 19, 1861, . . . — — Map (db m190078) HM
On South Cross Street at High Street, on the right when traveling south on South Cross Street.
Building built in 1883 by Thomas S. Bordley as a two-story men’s haberdashery. Gutted by fire in 1910. Rebuilt in 1911. Owned and operated as a men’s store by Carl and Ruth Bordley 1922-1950. Now rented by the Bordley family. — — Map (db m6157) HM
On South Queen Street just south of Cannon Street, on the right when traveling south.
You are looking at a rare survivor—a building that embodies the radical social change brought on by the Civil War. In 1882, 28 African American veterans of the United States Colored Troops (USCT) chartered the Charles Sumner Post #25, Grand Army . . . — — Map (db m199235) HM
On South Queen Street just south of Cannon Street, on the right when traveling south.
African American Civil War veterans constructed this meeting hall for Charles Sumner Post No. 25, Grand Army of the Republic (G.A.R.) in 1908. The hall is one of only two known to survive that were built for soldiers who served in . . . — — Map (db m156672) HM
Chestertown Historic District has been designated a Registered National Historic Landmark under the provision of the Historic Site Act of August 21, 1935. This site possesses exceptional value in commemorating or illustrating the history of the . . . — — Map (db m69840) HM WM
In remembrance of the people who built and nurtured Chestertown for 300 years including those who worked land and river and those in trade professions, and religious leaders who inspired the essential being and spirit of our town. From their . . . — — Map (db m69844) HM
On High Street at Cross Street (Maryland Route 289), on the left when traveling south on High Street.
County seat of Kent County. Established in 1706. Situated on the most traveled highway between south and north during the revolutionary period. George Washington made eight known visits here between 1756 and 1793. Rich in Colonial History. — — Map (db m3059) HM
Erected by James A. Pearce June 1917 in commemoration of the patriotism and valor of a once divided but now reunited county. To the soldiers of Kent in the Confederate Army 1861-1865
Captain William I. Rasin; Macall M. Rasin; George T. . . . — — Map (db m62822) HM
On Quaker Neck Road (Maryland Route 289) near Cliffs City Road, on the left when traveling west.
The last remaining one-room schoolhouse in Kent County. Erected in 1878 to serve a watermen's and farming community and was so used continuously until 1939. One teacher taught seven grades and as many as 46 students. — — Map (db m40195) HM
The people of Chestertown---a commercial center connected to international trade---generally opposed going to war with Great Britain. Yet when war came, most supported the American effort. Chestertown sent many distinguished fighters to battle.
The . . . — — Map (db m80629) HM
On North Cross Street (Maryland Route 289) at High Street, on the left on North Cross Street.
From this point
on
May 23, 1774
a group of Chestertown citizens
undisguised and in broad daylight
boarded the brigantine
Geddes
and threw its cargo of tea
into the
Chester River. — — Map (db m3060) HM
On Cross Street, 0.1 miles west of Maryland Route 213, on the right when traveling west.
George Vickers was born in Chestertown in 1801. He opposed secession in 1861. Assisted Governor Hicks to raise an Eastern Shore Regiment and attained the rank of Major General of Militia. In the trial of President Johnson, Senator Vickers voted for . . . — — Map (db m3049) HM
On Washington Avenue (Maryland Route 213) 0.1 miles south of North College Avenue, on the right when traveling south.
Benefactor of Washington College
Member of the
Board of Visitors and Governors
1784-1789
Honorary Degree Recipient 1789
A gift from the Class of 2000
in commemoration of the
Bicentennial of
George Washington's death . . . — — Map (db m138233) HM
On Maple Avenue (Maryland Route 213) just south of North Cross Street (Maryland Route 289), on the right when traveling north.
History
1845…The first Chestertown Fire Company was owned and maintained by the Mutual Fire Insurance Company. They paid $1,000 for a hand pumper in 1878 that was built in 1804 by Philip Mason, in Philadelphia. In . . . — — Map (db m199225) HM
On High Street near Cross Street (Maryland Route 289), on the left when traveling south.
In Memory of more than 400 prominent United States Colored Troops from Kent County, Maryland who bravely displayed extraordinary acts of heroism as they faithfully served their country with courage & honor in an attempt to gain freedom & equality in . . . — — Map (db m5414) HM
Near High Street, on the left when traveling south.
John Leeds Barroll first walked these courthouse grounds as a prominent Kent County lawyer before becoming a newspaper publisher. He was admitted to the bar in 1852 and served as the county State’s Attorney, 1854–1856, then founded the Kent . . . — — Map (db m186649) HM
Near High Street near Cross Street, on the left when traveling south.
On this site stood the courthouse built in 1707 which was burned and repaired in 1720. A new building was erected in 1860 and remodeled in 1937. — — Map (db m3065) HM
On High Street, 0.2 miles north of Cannon Street, on the left when traveling north.
The Chestertown waterfront seems quiet today, but it was a flashpoint in the American colonists' struggle for liberty.
Kent County, long loyal to England, found its ancestral ties weakening with each new generation born on American soil. . . . — — Map (db m138241) HM
On High Street, 0.2 miles north of Cannon Street, on the left when traveling north.
In colonial times, Chestertown was designated the primary port of entry for the upper Eastern shore.
Bustling wharves lined the waterfront, where laborers loaded ships with local crops bound for Europe and the Caribbean. Vessels from . . . — — Map (db m138239) HM
Early September 3, 1814, at Mitchell House, British raiders roused Joseph T. Mitchell and his wife from their bed, shot their horses, and abducted Mitchell. They believed he ws commissary general for all of Maryland.
His was a lesser job as . . . — — Map (db m80628) HM
Near High Street (Maryland Route 20) 0.2 miles west of Flatland Road (Maryland Route 514).
At the outbreak of the Civil War in 1861, George Vickers opposed secession and used his influence to keep Maryland in the Union. He became a major general of the 2nd Division, Maryland Militia, and helped form the 2nd Regiment Eastern Shore . . . — — Map (db m156850) HM
In Honor of
James Alfred Pearce
Born 1840 -- Died 1920
Distinguished Citizen - Eminent Jurist
Christian Gentleman
Chief Judge of Second Judicial Circuit
Member Court of Appeals of Maryland 1897 - 1912
Erected August 1, . . . — — Map (db m62849) HM
On Washington Avenue (Route 213) 0.1 miles south of North Kent Street, on the left when traveling south.
Here stood
The Kent County Free School
authorized and established
by act of
Council and Assembly of Maryland
September 26, 1728
This became Washington College
October 15, 1782 — — Map (db m138234) HM
On Calvert Street at College Avenue, on the right when traveling west on Calvert Street.
In 1945 former U. S. Army Sergeant Charlie Graves built a multi-enterprise operation on this site that featured a night club boasting top-notch décor, a restaurant, bar, billiards hall, and a package store. Ten years later in 1955, Charlie . . . — — Map (db m208435) HM
On High Street near Cross Street (Maryland Route 289), on the left when traveling south.
This Monument honors • the area Veterans • who have sacrificed • for their country.
World War I 1917–1918 • World War II 1941–1945 • Korean War 1950–1953 • Vietnam War 1964–1973. — — Map (db m3063) WM
On North Cross Street (Maryland Route 289) at Maple Avenue, on the right on North Cross Street.
Welcome to Kent County! The Civil War intruded into quiet Eastern Shore communities, and residents of this beautiful, water-laced region faced difficult choices.
In the years before the war, enslaved African Americans from the Eastern Shore . . . — — Map (db m190079) HM
On Washington Avenue at Brown Street, on the right when traveling south on Washington Avenue.
George Washington gave to its founding, granted use of his name and served on the Board of Visitors and Governors. He attended public exercises here, 1784, and received degree of Doctor of Laws in 1789. — — Map (db m3053) HM
On Cannon Street at High Street, on the right when traveling west on Cannon Street.
From the year 1642 until the end of the Civil War in 1865, slavery prevailed in Maryland. During that period, this harbor is where human beings captured from Africa were enslaved and transported to be bought and sold for the profit of free labor. . . . — — Map (db m208428) HM
In June 1917, Judge James A. Pearce commemorated the Civil War soldiers of Kent County by erecting a monument to honor the patriotism and valor of a once divided, but now reunited country. The rough-cut and polished granite monument behind you . . . — — Map (db m186803) HM
On North Water Street at High Street, on the left when traveling south on North Water Street.
Home of
Thomas Smyth, Sr. 1730-1819
Member of the
Maryland Council of Safety 1775-1776,
Commissary of Troops Kent County 1777.
His shipyard built the Maryland Navy
Galley "Chester", launched 1777. — — Map (db m138238) HM
“Swish”
Philadelphia A.L., 1936
Chicago N.L., 1939–1948
Philadelphia N.L., 1948–1953
Born Chestertown, Kent County, Eastern Shore of Maryland, 1914. Graduate of Washington College 1936. Feared and respected . . . — — Map (db m3058) HM
On Maryland Route 20 at Martin Wagner Road, on the right on State Route 20.
Master Machinist and Blacksmith, he was the third generation of his family to devote his life to work with forge, torch and anvil on this site. The Wagner Blacksmith and Machinery Repair Shop began serving the residents of Kent County in the 1850s. . . . — — Map (db m3071) HM
On Maryland Route 20, 0.3 miles north of Maryland Route 21, on the right when traveling south.
Kent County Militia under Lt. Col. Philip A. Reed marched from Belle Air (Fairlee) to meet British Forces here on August 31, 1814. The British with 15 killed, were repulsed and their commander, Sir Peter Parker, mortally wounded. American losses . . . — — Map (db m62512) HM
On Caulk's Field Road, 0.1 miles west of Maryland Route 21, on the right when traveling west.
The British commanded by Sir Peter Parker[,] Baronet and the Americans commanded by Col. Philip Reed met in engagement on this field Aug. 31st 1814[.] The British were defeated and Sir Peter Parker killed — — Map (db m156869) HM
On South Main Street (Maryland Route 313/290) at W. Cross Street (Maryland Route 213), on the left when traveling north on South Main Street.
On this site stood the tavern erected by William Downs in 1763. Burned in 1893. George Washington stopped here in 1774 en route to and from the first Continental Congress. He traveled this road on his eight visits to Kent County. — — Map (db m155488) HM
On Queen Street, on the left when traveling north. Reported damaged.
British Rear Admiral George Cockburn noted Georgetown and Fredericktown “were Places of some…Importance,” and the Sassafras the only upper river “I had not examined and cleared.” He led his full force toward the . . . — — Map (db m155762) HM
On Queen Street at Augustine Herman HIghway (Maryland Route 213), on the right when traveling north on Queen Street.
From opposite sides of the Sassafras River local militia fired at British raiders advancing toward Fredericktown and Georgetown May 5-6 , 1813. The militia fought only briefly before retreating, but the towns paid dearly. The British reduced . . . — — Map (db m155653) HM
On Maryland Route 213 at Queen Street, on the right when traveling south on State Route 213.
Erected by act of Assembly of Maryland, May 1736, on a tract called Tolchester. A base of Continental supplies, 1775 to 1783. Port of Entry and ferry landing. George Washington stopped here enroute to points north and south.
Burned by British . . . — — Map (db m155498) HM
Near Maryland Route 213, on the right when traveling south.
In Honor of
Mistress Kitty Knight
Revolutionary Belle and Beauty
A Friend of General George Washington
When the British burned Georgetown in 1813
Her Heroic Efforts Saved this
House which later became her home.
Placed by London . . . — — Map (db m154346) HM
On Maryland Route 213, 0.7 miles south of Maryland Route 444, on the left when traveling south.
Commander Penna Troops. Served at Princeton, Brandywine, Germantown and Monmouth. Incensed at the cabal against Washington he wounded Gen. Conway in a duel. Lived nearby and served in General Assembly of Maryland from Kent County. Buried in . . . — — Map (db m129181) HM
On Maryland Route 213, on the right when traveling south.
Son of Thomas Perkins, who built brick house near here in 1720. The Colonel was one of the commissioners appointed by Maryland Council of Safety to raise supplies for Washington’s army. Much of the flour provided from the Eastern Shore was ground in . . . — — Map (db m129179) HM
On May 6, 1813, the British landed barges at Turner’s Creek—a village of about 60 people and an active port for grains and flour. Resident John Stavely was forced to lead the enemy vessels to Fredericktown and Georgetown. After destroying . . . — — Map (db m80621) HM
On Maryland Line Road (Maryland Route 330) 1.6 miles east of Galena Road (Maryland Route 313), on the right when traveling east.
This aircraft, NC 18111, was an early production model, the 117th made, built for and operated by United Airlines from 1937 to 1954, American Flyers Airline 1954 to 1973 and Shawnee Airlines to 1980. The aircraft was donated to the Museum in . . . — — Map (db m189385) HM
On Maryland Line Road (Maryland Route 330) 1.6 miles east of Galena Road (Maryland Route 313), on the right when traveling east.
Mike Macario purchased the An-2 from the Air Mobility Command (AMC) Museum, Dover, DE and donated it to the Massey Museum in the name of his mother, Katherine (Kate) Macario. Longtime friend of Massey Aerodrome, Kate Macario passed away on . . . — — Map (db m189384) HM
On Maryland Line Road (Route 330) 1.6 miles east of Galena Road (Maryland Route 313), on the right when traveling east.
Life-size fiberglass model of
Chance-Vought F4U Corsair
WWII - Korean War Fighter
Marked as flown in 1949 by
Alberto H. Santa Maria
Commander U.S. Navy
1924 - 2010
Kent County, MD . . . — — Map (db m189382) HM
On Maryland Line Road (Maryland Route 330) 1.6 miles east of Galena Road (Maryland Route 313), on the right when traveling east.
This aircraft is a Russian designed, probably Polish built, Antonov AN-25 (NATO code name - Colt)
Largest of single engine Bi-planes, they were produced from 1948 until 2008 with 16,164 built (most in Soviet countries and China) . . . — — Map (db m189383) HM
On River Road (Maryland Route 291) 0.2 miles west of Chesterville Road (Maryland Route 290), on the left when traveling west.
Born in New Market, now Chesterville, where he lived with his family until they escaped slavery ca. 1822-24, settling in New York City. Abolitionist and activist, Presbyterian minister, teacher, founder of schools, college president, missionary and . . . — — Map (db m168190) HM
On Cypress Road (Maryland Route 291), on the right when traveling east.
The North-South line between the colonies of Maryland and Pennsylvania, now Delaware, was surveyed between June and September 1764 by Charles Mason, an astronomer, and Jeremiah Dixon, a mathematician and surveyor.
Leading a party of . . . — — Map (db m19671) HM
On River Road (Maryland Route 291) west of School Street, on the left when traveling west.
(Top of memorial)
To Honor the Veterans of All Wars
May They Rest in Peace
(Front of memorial)
Veterans Memorial
Erected by
Kent County Memorial
VFW Post 663
American Legion
Jeff Davis Post 18
Kent . . . — — Map (db m130453) WM
Captain Peter Parker arrived at Swan Creek in the HMS Menelaus August 20, 1814. The British had terrorized towns in the Upper Bay all summer, but Parker came with a special mission---to divert attention from a strike against the U.S. Capital.
While . . . — — Map (db m80634) HM
For centuries, people have made their living on the water here at Rock Hall. Earliest accounts of the place relate that fisherman hauled in enormous amounts of rockfish; some believe the fish gave the town its name.
A Working Waterfront . . . — — Map (db m69896) HM
Keen eyes spot prey from 3,000 feet away. T he hunt begins for the raptor. Wings spread outward while the powerful feet extend downward. The sharp, heavy talons grasp hold of the unsuspecting animal. Soon a hooked beak will tear it apart. The hunt . . . — — Map (db m69897) HM
The aquatic ecosystem of Chesapeake Bay supports a remarkable diversity of sea creatures.
From bottom-dwellers to swimmers to reef-clutching shellfish, the Bay environment produces more than $175 million in commercial harvests each year. . . . — — Map (db m69889) HM
On Maryland Route 20 at Main Street (Maryland Route 445), on the right when traveling west on State Route 20.
One of senior officers of Continental Navy in opening years of Revolutionary War. Noted for his daring raids on British shipping. In his Sloop of War Reprisal he took Benjamin Franklin to France in 1776. Was first American Naval Officer in . . . — — Map (db m3072) HM
Lieutenant Colonel Philip Reed and his Maryland militia allegedly tried to fool British Troops at anchor off the Chester River. He directed his small force of cavalry to ferry back and forth between mainland and Eastern Neck Island, hoping British . . . — — Map (db m80652) HM
On Rock Hall Avenue just east of Beach Road, on the right when traveling east.
The village was named for the steamboat Gratitude, which from 1888 to 1914 made regular stops here and in Centreville from the Light Street Piers in Baltimore. Before the advent of motor transport, steamboats opened remote towns to commerce, . . . — — Map (db m138231) HM
Much like people travel to their destinations on interstate highways, birds migrate along flyways. Many different roads lead onto major highways. The same is true for flyways: birds fly to the major routes from various starting points and fly to . . . — — Map (db m69915) HM
The geography of Rock Hall puts it smack dab in the middle of a well-traveled transportation route. From the beginning, it served as a key ferry terminus linking the Eastern and Annapolis shores. Our nation’s founding fathers, traveling . . . — — Map (db m69894) HM
On Hawthorne Street at Sharp Street, on the left when traveling east on Hawthorne Street.
Site of Rock Hall Mansion for which the town was named. Landing of Annapolis - Rock Hall Packet used by George Washington on eight known trips through Kent County. A convenient route used by many prominent persons of Colonial and Revolutionary . . . — — Map (db m3074) HM
On Sharp Street at Main Street (Maryland Route 445), on the right when traveling east on Sharp Street.
Formerly known as Rock Hall Cross Roads. Main Street is part of first road cut in Kent County in 1675. George Washington passed here eight known times. Tench Tilghman used this route from Yorktown to Philadelphia in October 1781. — — Map (db m3075) HM
On Maryland Route 20 at Main Street (Maryland Route 445), on the right when traveling west on State Route 20.
Fishing shanty & wintertime portable home for waterman. Towed to suitable sites. Refurbished thru Friends of Stanley Rock Hall Lions. — — Map (db m3073) HM
On Eastern Neck Road, on the right when traveling south.
Major Joseph Wickes, who settled on Eastern Neck Island c. 1658, was Chief Justice of Kent County. Before 1674 the Court met at Wickliffe, his home here (no longer standing). By 1680 he had acquired 864 acres, the southern half of the island, which . . . — — Map (db m3076) HM
On Still Pond Road (Maryland Route 292) at Old Still Pond Road, on the left when traveling south on Still Pond Road.
In the village of Still Pond, twelve years before the 19th Amendment established women’s suffrage, Mary Jane Clark Howard, Anne Baker Maxwell and Lillie Deringer Kelley cast their ballots in the municipal election of 1908. That year, an act for . . . — — Map (db m3052) HM
On Tolchester Beach Road (Maryland Route 21) 1.4 miles west of Tolchester Road (Maryland Route 445), on the right when traveling west.
Opened on this site in 1877 by the Tolchester Steamboat Company, in an era when the steamboat was a primary mode of social and commercial transportation in the Tidewater region, and in response to the rising popularity of resorts and amusement . . . — — Map (db m19449) HM
The house before you - known as Knock's Folly - has witnessed more than 200 years of history. Henry Knock constructed the original clapboard log portion of the house around 1753. Donaldson Yeates bought the log house in 1770. After his death, his . . . — — Map (db m64354) HM
On Turners Creek Road, on the right when traveling south.
Agricultural Demonstration Area
this demonstration field shows how a farmer can grow crops on a steep slope while preventing soil erosion. The Grassed Diversion in the middle of the field funnels water into the Waterways that . . . — — Map (db m162790) HM
In 1608, English explorer Captain John Smith conducted two expeditions on the Chesapeake Bay. He was charged by the Virginia Company to seek precious metals and a water passage to the Pacific. His first voyage focused on the Bay's western shore. His . . . — — Map (db m64349) HM
Near Turners Creek Road, on the right when traveling north.
This house illustrates the almost extinct dwellings of the early 1800's that housed slaves/servants of Maryland's Eastern Shore. Believed to have been built as slave quarters and later as part of the African American community in Chestertown. The . . . — — Map (db m64511) HM
In the 1800's a corn crib was the place to dry and store corn. After harvesting, corn on the cob was placed in the crib. Air circulated through the slats in the side to allow the corn to dry. The kernels were then removed from the cob and stored in . . . — — Map (db m64510) HM
More than 3,600 species of plants, fish and wildlife live in the Chesapeake Bay region. the Sassafras River and Turner's Creek - tributaries of the Bay - provide food and shelter for great blue herons, osprey, otters, beaver, largmouth bass and . . . — — Map (db m64356) HM
The American Indians of the Sassafras region - known as the Tockwogh - survived by harvesting the rich bounty of plants and animals of the Chesapeake. They netted rockfish and other finfish, gathered shellfish and crabs during low tides, hunted deer . . . — — Map (db m64351) HM
On Turners Creek Road, on the right when traveling north.
From the headwaters near the Route 301 Bridge to the river's mouth between Grove Point and Howell Point, the Sassafras River Water Trail winds past forested shorelines, bucolic farms, and high sandy cliffs for 18 miles before reaching its confluence . . . — — Map (db m64294) HM
On Turners Creek Road, on the right when traveling north.
The "Settlement at Turner's Creek" was developed by Donaldson Yeats before the Revolutionary War. It was a hub for trade. At its peak, there was a shipyard, a tannery, a granary and a dock for shipping and receiving products. The Sassafras River . . . — — Map (db m64295) HM
On Turners Creek Road, on the right when traveling north.
Step back to the days of the small family farm and see the tools and equipment that made life easier. Most people did not travel far from home - going to Baltimore was a major undertaking! Farm products were shipped to market by custom Chesapeake . . . — — Map (db m64509) HM
On Saint James Newtown Road (Maryland Route 297) 0.1 miles south of Newtown Road, on the right when traveling south.
Worton Point 'Colored' Public School #2, District Number 3; a one-room schoolhouse built August 1890. This structure was documented by the University of Delaware Center for Historic and Architectural Design in June 2003. Prior to the 1930's . . . — — Map (db m62847) HM
Lieutenant Colonel Philip Reed, buried here in 1829, excelled among Maryland militia officers. Reed countered several of the British hit-and-run raids along the Eastern Shore. His men fended off the enemy’s attack at Worton Creek and claimed victory . . . — — Map (db m80622) HM
