Pomona, Maryland

Clark's Conveniency is a historic home located near Pomona, Kent County, Maryland, United States. It is a 1+1⁄2-story, early-18th-century brick house built in three sections: the main block and a wing on the east and west ends. It is representative of the houses built by the smaller but still prosperous planters of 18th-century tidewater Maryland.Clark's Conveniency was listed on the National Register of Historic Places in 1975.

Airy Hill is a historic home located at Chestertown, Kent County, Maryland, United States. It is a two-section dwelling consisting of a 1+1⁄2-story frame wing and a two-story Federal-style brick house. The brick section was added in the early 1790s, together with a middle section that now connects the two. Also on the property is a brick smokehouse and an early-19th-century cemetery.Airy Hill was listed on the National Register of Historic Places in 1996.

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.

Reward-Tilden's Farm, or The Reward, is a historic home located at Chestertown, Kent County, Maryland. It is a three bay long, two bay deep, two story, brick dwelling which appears to have been constructed in the 1740s.It was listed on the National Register of Historic Places in 1977.

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.

Langford is an unincorporated community in Kent County, Maryland, United States. Langford is located along Maryland Route 446 on Broad Neck, 4.25 miles (6.84 km) west-southwest of Chestertown.

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.

Brampton is a historic home located at Chestertown, Kent County, Maryland. It is a transitional Greek Revival / Italianate-influenced dwelling built about 1860. The main section of the house is a three-story structure, constructed of brick with a symmetrical five-bay-wide facade and a depth of two bays. A two-story frame wing extends from the rear.It was listed on the National Register of Historic Places in 1983.

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.

Chestertown is a historic railway station built in 1902–03 for the Pennsylvania Railroad and located in Chestertown, Kent County, Maryland. It is a 1+1⁄2-story, 17-by-47-foot (5.2 by 14.3 m) Queen Anne–style building. It features a hip roof with a wide bracketed overhang that provided shelter for train passengers on all four sides.It was listed on the National Register of Historic Places in 1982 as the Chestertown Railroad Station.

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.

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.