Pine Street Neighborhood Historic District

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.

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

Dorchester County Courthouse and Jail is a historic courthouse building located at Cambridge, the county seat of Dorchester County, Maryland. It is an Italianate influenced, painted brick structure, which was enlarged and extensively remodeled with Georgian Revival decorative detailing in the 1930s. The building entrance is flanked on the north by a three-story tower. It was constructed in 1853, and is the only courthouse designed by Richard Upjohn in Maryland.The County Jail, which stood to the southeast of the courthouse from about 1882 until its demolition in 1994, was a Queen Anne and Romanesque Revival style granite structure with brick and terra cotta features. The jail was the work of the Baltimore architect, Charles L. Carson.It was listed on the National Register of Historic Places in 1982.

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.

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.

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 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.

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.

Cambridge-South Dorchester High School is located in Cambridge, Maryland, United States, is part of the Dorchester County Public Schools system, and serves students in grades 9 to 12. The school opened in 1976 and cost $9 million to build and equip. Designed by architects Johannes and Murray of Silver Spring, the school's most prominent feature is its circular design.

Algonquin is a census-designated place (CDP) in Dorchester County, Maryland, United States. The population was 1,241 at the 2010 census. The community was named for the Algonquin people, one of the Native American tribes in the East.