Charles Sumner Post No. 25, Grand Army of the Republic

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.

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 Denton House, also known as the Denton-Weeks House, the River House, and the Smyth-Letherbury House, is a historic residence at 107 Water Street in Chestertown, Maryland. It is a three-story brick building, with a five-bay front facade framed by corner pilasters with stone capitals. The building has a raised basement, with a stone stringcourse between it and the first floor. The front entrance is centered, with an elaborate surround consisting of pilasters, entablature and dentillated gable. The house was built about 1784 by Richard Smyth, the son of one of the area's wealthiest merchants. In 1791 it was bought by Peregrine Letherbury, the first law professor at Washington College.The house was listed on the National Register of Historic Places in 1971, and it is a contributing property in the Chestertown Historic District.

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.

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 Historic District is a historic district in Chestertown, Maryland. It was listed on the National Register of Historic Places and designated a National Historic Landmark in 1970, and its area was increased in 1984. The town on the Chester River, became the chief port for tobacco and wheat on the Eastern Shore of Maryland between 1750 and 1790. The port declined thereafter, as Baltimore became the major port for such activity. In consequence, Chestertown acquired a collection of more than fifty Georgian style town houses. The 18th-century residential area survived without harm a 1910 fire that destroyed the central business district of Chestertown.The historic residential area is concentrated along Water Street between the business district and the Chester River. Highlights include: Hynson-Ringgold House ("The Abbey"), 100 South Water Street. Built in 1767 by merchant Thomas Ringgold by uniting two adjoining 1735 houses into a three-art house. Interiors were designed by William Buckland between 1767 and 1771. The original Chippendale-Georgian paneling in the drawing room was removed and installed at the Baltimore Museum of Art in the 1920s. The house was restored in the 1930s and is the residence of the president of Washington College. Custom House, 101 South Water Street. A three-story brick house in two parts, stated to have been built by the Ringgold family in the 1746. The first floor was used as a warehouse, with living quarters on the upper levels. The building was used as Chestertown's custom house. The rear section was added in 1771. Widehall, 101 North Water Street. Individually listed on the National Register of Historic Places, Widehall was built by Thomas Smythe about 1770. The house's exterior has been altered from the original Georgian style, while elaborate interiors remain. River House, also known as the Denton House, 107 North Water Street. Built between 1737 and 1743 by William Timbrill, a Barbados merchant. The interiors are Georgian, while the exterior has been modified in Greek Revival style. The paneling of the third floor master bedroom was purchased by the Winterthur Museum in 1926.A number of other structures on Water Street, High Street and Queen Street are included. Denton House and Widehall are also individually listed Registered Historic Places included in the district.

Washington College is a private liberal arts college in Chestertown, Maryland. Maryland granted Washington College its charter in 1782. George Washington supported the founding of the college by consenting to have the "College at Chester" named in his honor, through generous financial support, and through service on the college's Board of Visitors and Governors. Washington College is the 10th-oldest college in the United States and was the first college chartered after American independence. The school became coeducational in 1891.

Chestertown is a town in Kent County, Maryland, United States. The population was 5,252 as of the 2010 census. It is the county seat of Kent County.

The Radcliffe Mill is a historic grist mill and related structures located in Chestertown, Kent County, Maryland, United States. It consists of a Mill Building, built in 1891; Grain Elevator, probably constructed around 1924; and Annex / Seed House. The complex is historically significant for its association with the development of agriculture and the associated grist milling industry in Kent County. The present complex occupies land along Radcliffe Creek that has been associated with milling for about 300 years. A mill operated in this approximate location from 1694 until 1997.The Radcliffe Mill was listed on the National Register of Historic Places in 2006.

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.

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