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
On Cannon Street east of High Street, on the right when traveling east.
Meet Echo Hill Outdoor School's fleet of historic Chesapeake workboats!
Since 1972, Echo Hill Outdoor School has been connecting children to nature through the magic of playing, learning and exploring in the outdoors. The school's . . . — — Map (db m273577) 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
On Cannon Street east of High Street, on the left when traveling east.
Her Story
Annie D is a Chesapeake buyboat, built in Deltaville, Virginia in 1957 for waterman, Thomas Asbury. Buyboats are the Bay's tractor trailers, built to transport fish, oysters, lumber and produce all over the Chesapeake.
Echo . . . — — Map (db m273596) 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 Cannon Street east of High Street, on the left when traveling east.
This versatile, all-around skiff is known as a "bateau." With a flat bottom and a shallow draft, Ric was built for the protected waters of rivers and creeks. At the turn of the century, watermen used bateau like Ric throughout the seasons, . . . — — Map (db m273582) HM
On Caulks Field Road, on the right when traveling west.
To Commemorate the
Battle of Caulk's Field
Bicentennial
Old enemies unite, remember the past and look to the future as allies. We honor and pay tribute to the heroic men of the Maryland Militia commanded by . . . — — Map (db m295596) WM
On South Cross Street (Maryland Route 289) south of Cannon Street, on the right when traveling north.
For thousands of years, Native Americans planted, fished, hunted, and built communities along the banks of the Chester River — developing knowledge and practices that still influence life here today.
After colonists arrived, indigenous . . . — — Map (db m273553) HM
On North College Avenue south of Prospect Street, on the left when traveling south.
The original structure was built on Kent and Calvert Streets in 1878 and remained there until it was destroyed by fire. A new church was erected on this site in October 1910, becoming an anchor throughout the struggles of the local Black . . . — — Map (db m302841) 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. Reported permanently removed.
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 ( 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
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 Cannon Street east of High Street, on the left when traveling east.
Her Story
The Elsworth is an original Chesapeake Bay skipjack, built in 1901 by Mitchell Hubbard in Hudson, MD. Hubbard was assisted by Robert Thomas and William Seward. Construction was commissioned by Hilory Wingate, and named after his . . . — — Map (db m273605) HM
On North Cross Street at Memorial Plaza, on the right when traveling north on North Cross Street.
In solemn remembrance of and with gratitude for those enslaved persons who through their involuntary labor and sacrifice made possible the founding and preservation of this church, originally named Chestertown Chapel, 1766. — — Map (db m302862) 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 High Street (Maryland Route 20) east of Flatland Road, on the right when traveling east.
This former truck storage yard was redesigned to reduce impervious surfaces and provided wildlife habitat through the use of native trees, bushes and grasses. The adjacent Radcliffe Creek, which feeds into the Chester River, benefits from . . . — — Map (db m302861) HM
On Cross Street 0.1 miles west of 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 Cannon Street east of High Street, on the left when traveling east.
Born and raised in Chestertown, Maryland, Gilbert Byron was an author and teacher. His work includes hundreds of poems, novels, short stories and newspaper columns, inspired by the Chester River and its mother, Chesapeake Bay.
The son of a . . . — — Map (db m273607) HM
On High Street north of Cannon Street, on the left when traveling north.
In colonial times, Chestertown was the primary port for the upper Eastern Shore.
Bustling wharves lined the waterfront as laborers loaded ships with local crops, such as wheat and tobacco, bound for Europe and the Caribbean. vessels from . . . — — Map (db m273619) HM
On Calvert Street west of North Kent Street, on the right when traveling west.
Garnet School, built 1916, was a wooden structure located on College Avenue, built under the leadership of Emma L. Grason Miller, Kent County's first Black Supervisor of Colored Schools 1911-1922. Its first graduating class of five students was . . . — — Map (db m302847) HM
On Maple Avenue (Maryland Route 213) just south of North Cross Street ( 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 ( 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 . . . — — Map (db m5414) WM
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
On High Street east of South Water Street, on the right when traveling north.
This plaza is donated by
John E. Barnes
in honor of his grandfather
John W. Barnes
1856 - 1941
Elected as one of the first Mayors of Chestertown in 1929 — — Map (db m273622) HM
On North Cross Street north of Park Row, on the left when traveling north.
Lynching in America. Over 6,500 Black people were victims of lynching in the United States between 1865 and 1950. After the Civil War, lynching emerged as the most notorious and public form of racial terrorism used to enforce racial hierarchy . . . — — Map (db m301685) 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
Near South Cross Street (Maryland Route 289) south of Cannon Street, on the right when traveling north.
This project was initiated by the Chestertown Garden Club and made possible by a grant from The Chesapeake Bay Trust.
Special thanks to the town of Chestertown for their ongoing support of the project and to The Chesapeake Bay . . . — — Map (db m273562) HM
On South Cross Street (Maryland Route 289) south of Cannon Street, on the right when traveling north.
In 2008, the Town of Chestertown and Washington College's Center for Environment & Society conducted a tree canopy study of the town. Based on that survey and recommendations from the US Forestry Service, an Urban and Community Forest Master Plan . . . — — Map (db m273556) 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 . . . — — Map (db m138241) HM
On Caulks Field Road, on the right when traveling west.
This Stone has been Laid
In Memory of the
Royal Navy
and
Royal Marines
Servicemen Killed During the
Battle of Caulk's Field
on the 31st Day of August in the Year of 1814
Sir Peter . . . — — Map (db m295593) WM
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
On Cannon Street east of High Street, on the left when traveling east.
Further down the waterfront, past the old Chestertown wharf, was the African American community of Scott's Point. Here, Black watermen worked on the water, catching oysters, crabs and fish on the same waterways as their enslaved ancestors. . . . — — Map (db m273604) HM
Near High Street (Maryland Route 20) 0.2 miles west of Flatland Road ( 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
On South Lynchburg Street, on the right when traveling south.
Fireworks explosion on July 16, 1954, that claimed the lives of eleven employees.
This marker was placed by the Cadwalader of Kent Questers on the occasion of the 70th Anniversary of the tragedy. — — Map (db m266022) HM
On Cannon Street east of High Street, on the left when traveling east.
Echo Hill also has two other floating outdoor classrooms, the historic Chesapeake workboats Spirit and Twilight. Spirit is a classic deadrise built by Stanley Vansant in 1944. She was acquired by Echo Hill in 1978. Twilight is a Potomac River . . . — — Map (db m273611) HM
On Cannon Street east of High Street, on the left when traveling east.
Stanley Vansant built boats and worked the waters of Kent County, Maryland. From his boatyard in Long Cove, off the lower Chester River's Piney Neck, he constructed hundreds of bateau and deadrises. Their rugged quality and beauty made for local . . . — — Map (db m273592) HM
On Cannon Street east of High Street, on the left when traveling east.
For over a century—from April 1821 to December 1923—passenger and freight steamboats played a major role in the life of the Chester River and Chestertown. In the era before highways, bridges and railroads, steamers offered reliable, regularly . . . — — Map (db m273601) HM
On Cannon Street east of High Street, in the median.
The schooner Sultana is part of the larger Chestertown campus of the Sultana Education Foundation. Since 1997, the Foundation has provided award-winning programs in history and environmental science for tens of thousands of students, . . . — — Map (db m273613) 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 Cannon Street east of High Street, in the median.
The schooner Sultana is a reproduction of a Boston-built merchant vessel purchased by the Royal Navy and used to enforce the hated "Tea Taxes" from 1768 to 1772. During Sultana's four year tour of duty, over 100 men from three continents . . . — — Map (db m273617) HM
On Washington Avenue (Route 213) 0.2 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, 1723
This became Washington College
October 15, 1782 — — Map (db m274231) 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 ( 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 Cannon Street east of High Street, on the left when traveling east.
For centuries, the Chesapeake Bay has shaped life along its waterways. Rich in natural resources, with extensive rivers that served as highway for travel and commerce, the Bay's environment has fostered human habitation, culture, and industry . . . — — Map (db m273602) HM
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 South Cross Street (Maryland Route 289) south of Cannon Street, on the right when traveling north.
In the fall of 2009, wooden bulkheading was removed at this location in order to restore, enhance and protect the Chester river's natural shoreline. A living shoreline, unlike the traditional "armor" such as stone revetments. It creates essential . . . — — Map (db m273566) HM
On Maryland Route 20 at Martin Wagner Road, on the right on Maryland 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
Near Sandy Bottom Road 0.1 miles north of Sandy Bottom Road & Ricauds Branch Road.
At 7:40 a.m. on the morning of December 9, 2015, the sound of the first firing up of a chain saw was heard around the parking lot of St. Paul's Parish, Kent. It was time to begin the felling of the 400-year-old United States Champion Swamp . . . — — Map (db m224326) HM
On Rock Hall Road (Maryland Route 20) 0.3 miles north of Tolchester Beach Road ( 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 m247358) HM
On Caulk's Field Road 0.1 miles west of 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 ( 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 ( 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 Maryland 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 Augustine Herman Highway (Maryland Route 213) north of Georgetown Cemetery Road, on the left when traveling north. Reported unreadable.
Here and here abouts are the grounds of Westminster Presbyterian Church and its burial grounds.
Founded in 1786, two Presbyterian meeting houses were [unreadable] was held to raise funds [unreadable], one here in Georgetown and [unreadable]. . . . — — Map (db m307066) HM
On Maryland Route 213 0.7 miles south of 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 ( 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 ( 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 ( 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 ( 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 ( 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
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