Kennersley

The Island Image is a Chesapeake Bay log canoe, built in 1885 at Elliot's Island, Maryland, by Herman Jones and Isaac Moore. It is 29'-8½" long with a beam of 5-10¼", and has a straight, raking stem and a sharp stern. It is privately owned, and races under No. 17. It is one of the last 22 surviving traditional Chesapeake Bay racing log canoes that carry on a tradition of racing on the Eastern Shore of Maryland that has existed since the 1840s. She is located at Chestertown, Kent County, Maryland.The Island Image was listed on the National Register of Historic Places in 1985.

Godlington Manor is a historic home located at Chestertown, Kent County, Maryland, United States. It is a frame gambrel-roof structure with a long frame 1+1⁄2-story kitchen wing. The house features much of the original beaded clapboard. Also on the property is a frame milkhouse, a brick smokehouse, and a boxwood garden.Godlington Manor was listed on the National Register of Historic Places in 1972.

Chester Hall, also known as Rye Hall, is a historic home located at Chestertown, Queen Anne's County, Maryland, United States. It is a large brick Georgian / Federal style Flemish bond brick dwelling constructed in the 1790s. The house measures approximately 48 feet by 36 feet and is two stories tall above a high basement.Chester Hall was listed on the National Register of Historic Places in 1980.

Readbourne is a historic home on the Chester River located at Centreville, Queen Anne's County, Maryland, United States. It is a five-part Georgian brick house: the center block was built in the early 1730s; the south wing in 1791; and the north wing in 1948. The central part of the house is the most significant, being a T-shaped, two-story brick building with a hip roof, measuring 60 feet (18 m) by 23 feet 6 inches (7.16 m). All of the brick walls are laid in Flemish bond.The house was listed on the National Register of Historic Places in 1973. It was built by James Hollyday, a prominent politician for the Province of Maryland. It was once owned by William Fahnestock Jr. of the New York banking family.

The Mystery is a Chesapeake Bay log canoe, built in 1932, by Harry Sinclair in Oxford, Maryland. She measures 34'-7" long, has a beam of 8'-81⁄2" and has a centerboard. She is noted for her very tall masts, is privately owned, and races under No. 8. She is one of the last 22 surviving traditional Chesapeake Bay racing log canoes that carry on a tradition of racing on the Eastern Shore of Maryland that has existed since the 1840s. She is located at Kingstown, Queen Anne's County, Maryland.She was listed on the National Register of Historic Places in 1985.

Kingstown is a census-designated place (CDP) in Queen Anne's County, Maryland, United States. The population was 1,644 at the 2000 census.

The Silver Heel is a Chesapeake Bay log canoe, built in 1902, in Kent County, Maryland by Eugene Thompson for John Wesley Dickinson. She is a 33'-113⁄4" sailing log canoe in the racing fleet. She has a beam of 7'-3/4". She has a clipper bow, with the longhead braced to serve as a bowsprit, and a straight, raking stern. The canoe is privately owned and races under No. 2. She one of the last 22 surviving traditional Chesapeake Bay racing log canoes that carry on a tradition of racing on the Eastern Shore of Maryland that has existed since the 1840s. She is located at Chestertown, Kent County, Maryland.She was listed on the National Register of Historic Places in 1985.

The Sergeant First Class John H. Newnam Armory, also known as the Chestertown Armory, is a historic National Guard armory built in 1931 and located in Chestertown, Kent County, Maryland, United States. From 1933 until 2005 it housed various formations from the Maryland Army National Guard. It also was the home of sporting and community events during this time. After the 115th Infantry Regiment was merged into the 175th Infantry Regiment in 2005, the armory was declared to be surplus by the state of Maryland. The Chestertown Armory was transferred to Washington College in 2013. Since then, it has stood vacant. The college is investigating the possibility of turning it into a bed and breakfast.

Bernice J. is a Chesapeake Bay skipjack, built in 1904 in Young's Creek, Virginia, by W. Thomas Young of Parksley, who also built Claude W. Somers. She is a 42-foot-long (13 m) two-sail bateau, or "V"-bottomed deadrise type of centerboard sloop, commonly referred to as a skipjack. She worked dredging oysters through the 1970s. She is located at Chestertown, Kent County, Maryland.She was listed on the National Register of Historic Places in 1985.

The Hynson–Ringgold House, sometimes known as The Abbey, is the official residence of the president of Washington College. The building is in the Georgian style and is made entirely out of brick. In the rear of the building there is a large enclosed garden. It sits on the corner of Cannon Street and Water Street in Chestertown, Maryland.

Widehall is a historic and architecturally significant house in Chestertown, Kent County, Maryland. Built by Thomas Smyth III, 1769–1770, it is a contributing property in the Chestertown Historic District.

Charles Sumner Post #25, Grand Army of the Republic is a historic fraternal lodge building located in Chestertown, Kent County, Maryland. Named after Charles Sumner, it was constructed as a meeting hall about 1908 and is a two-story gable-front frame building, built on brick piers, with a rectangular floor plan. It is located in the Scotts Point area, a historically black area within the Chestertown Historic District, and was abandoned between 1985 and 2002. It is one of only two Grand Army of the Republic halls for African-American veterans known to survive in the Nation.It was listed on the National Register of Historic Places in 2005. In 2012, Preservation Maryland placed the Charles Sumner Post #25 on its list of threatened historic properties.The building has been restored by the Kent County Arts Council and opened to the public in 2014 as a museum of American Civil War history and the role of African-Americans in the war.