Dorchester County Courthouse and Jail

Christ Episcopal Church and Cemetery is an historic Episcopal church and cemetery located at Cambridge, Dorchester County, Maryland U.S.A.

The Goldsborough House is a historic home located at Cambridge, Dorchester County, Maryland, United States. It is a two-and-a-half-story painted brick Federal-style house with a five-bay symmetrical facade, built about 1793. The house features an Ionic columned entrance portico.The Goldsborough House was listed on the National Register of Historic Places in 1988.

Sycamore Cottage is a historic home located at Cambridge, Dorchester County, Maryland, United States. It was built possibly as early as 1765. The house is a 1+1⁄2-story gambrel-roofed frame structure. Remodelings during the 19th century include adding Victorian windows, a central Colonial Revival entrance porch, 1840s Greek Revival interior decorative detailing, and the addition of a large one-story meeting hall. It was moved to this location in 1840. Since 1922, Sycamore Cottage has been the headquarters of the Cambridge Woman's Club.Sycamore Cottage was listed on the National Register of Historic Places in 1988.

Cambridge is a city in Dorchester County, Maryland, United States. The population was 13,096 at the 2020 census. It is the county seat of Dorchester County and the county's largest municipality. Cambridge is the fourth most populous city in Maryland's Eastern Shore region, after Salisbury, Elkton and Easton.

Cambridge Historic District, Wards I and III is a national historic district in Cambridge, Dorchester County, Maryland. It is a large residential, commercial, and governmental area in the northwest section of the city. It consists of buildings from the late 18th through the mid 20th century. Residential building styles include Georgian, Queen Anne, Colonial Revival, and American Foursquare. The district includes the Italian Villa style courthouse designed by Richard Upjohn.It was added to the National Register of Historic Places in 1990.

The Pine Street Neighborhood Historic District encompasses a neighborhood of Cambridge, Maryland with more than 150 years of history as an African-American neighborhood. The district covers about 100 acres (40 ha) of Cambridge, centered on the triangular intersection of High, Washington, and Pine Streets. It is a predominantly residential area with some commercial development. The majority of the district's housing consists of somewhat uniform factory worker housing. There are rows of two-story, two-bay, gable-front frame houses, sometimes with four-bay duplexes.The district was listed on the National Register of Historic Places in 2012.

Glasgow is a historic home located at Cambridge, Dorchester County, Maryland. It is a Federal style, gable-front, 2+1⁄2-story brick house built about 1792. Attached is a 1+1⁄2-story frame wing dating from the early 20th century. Local history sometimes holds that the home was the birthplace of William Vans Murray, but land records and Murray's biographical data both indicate that it is unlikely that it was ever his home. It is possible, however, that Murray stayed there for some time after his return from his service as foreign minister in the Netherlands, with his first cousin William Murray Robertson, the owner at the time.It was listed on the National Register of Historic Places in 1976.

The Patricia is a Chesapeake Bay log canoe built in 1942 by Oliver Duke. She measures 27'-4" long, and has a beam of 6'-43⁄4". The Patricia has a slightly hollow longhead bow and a sharp stern. Painted white, the canoe races under the no. 19. She is one of twenty-two traditional Chesapeake Bay racing log canoes existing today. The Patricia, and boats like her, carry on a tradition of racing on the Eastern Shore of Maryland that has existed since the 1840s. She is located at Cambridge, Dorchester County, Maryland.She was listed on the National Register of Historic Places in 1985.

LaGrange, also known as La Grange Plantation or Meredith House, is a historic home located at Cambridge, Dorchester County, Maryland, United States. It was built about 1760. The house is a 2+1⁄2-story Flemish bond brick house and is one of the few remaining Georgian houses in the town. Sun porches and a frame wing were added to the main house in the late 19th and early 20th centuries. Three outbuildings remain, including a late 19th-century dairy, an 18th-century smokehouse, and a 20th-century garage.LaGrange was listed on the National Register of Historic Places in 1980.

The Harriet Tubman Memorial Garden is part of the Harriet Tubman Underground Railroad Byway (Maryland) and is located in Cambridge, Maryland. It honours the life of abolitionist Harriet Tubman and the journeys of the many people she assisted to escape slavery. The garden features information boards and murals, some of which were painted by Charles Ross, a relative of Tubman's.

Annie Oakley House is a historic home located at Cambridge, Dorchester County, Maryland. It is a 1+1⁄2-story, brick-and-frame, Colonial Revival–influenced bungalow constructed in 1913. Behind the house is a small garage and studio apartment. The house overlooks Hambrooks Bay, a protected body of water off the Choptank River. It was constructed as a retirement home for Annie Oakley and her husband, Frank Butler, and is the only surviving property in the nation that was either owned or occupied by Oakley as her primary and permanent residence. It features built-in shelves originally intended to display shooting trophies.It was listed on the National Register of Historic Places in 1996.

The Frederick C. Malkus Bridge, also known as the Choptank River Bridge, is a four-lane none-span beam bridge across the Choptank River in Maryland. Built in 1987 to replace the aging Emerson C. Harrington Bridge, the new bridge was named after Maryland state senator Frederick Malkus. U.S. Route 50 (US 50) crosses the river over the bridge between the towns of Cambridge and Trappe. The bridge is made of pre-stressed and pre-cast concrete.