Washington Academy and High School

The Manokin Presbyterian Church is a historic church located in Princess Anne, Somerset County, Maryland. It is a 1+1⁄2-story brick structure with a three-story entrance tower on the east end. The walls of the main section were built in 1765, and the tower was added in 1888. It is one of the first organized Presbyterian Churches established in America. In 1672, a group of Scotch-Irish Presbyterians who had settled on the Eastern Shore of Maryland, petitioned the Grand Jury of Somerset County for a civil permit to hold services of worship and to have their own minister. The permission was granted, and Robert Maddox was called by the Grand Jury to preach on the third Sunday of each month, at the home of Christopher Nutter, 'at the head of the Manokin River,' the present site. In 1680 a request was sent by Colonel Stevens of Rehobeth to the Presbytery at Laggan, Ireland, for an ordained minister, and three years later, in answer to that request, the Reverend Francis Makemie, a 25-year-old, recently ordained minister, arrived in Somerset County. Under his leadership, this church, and those at Rehobeth, Pitts Creek, Snow Hill, and Wicomico were organized.It was listed on the National Register of Historic Places in 1976.

John Woodland Crisfield (November 8, 1806 – January 12, 1897) was a U.S. Congressman from Maryland, representing the sixth district from 1847 to 1849 and the first district from 1861 to 1863. The city of Crisfield, Maryland, is named after him. Crisfield was a strong supporter of the Union during American Civil War, opposing moves towards Maryland's secession. However, Crisfield also supported the institution of slavery and worked to prevent its abolition in Maryland.

Princess Anne is a town in Somerset County, Maryland, United States, that also serves as its county seat. Its population was 3,290 at the 2010 census. It is included in the Salisbury, Maryland–Delaware Metropolitan Statistical Area. It is home to the University of Maryland Eastern Shore and the Teackle Mansion.

The Princess Anne Historic District is located in Princess Anne the county seat of Somerset County, Maryland on Maryland's Eastern Shore. There has been little change due to industry or other development, and the town retains much of its historic character since its founding in the early 18th century. It has been the governmental center since the county was formed in 1742 and the present courthouse is one of the most architecturally distinguished in the state. Within the historic district are a few pre-Revolutionary structures, a high concentration of Federal and Victorian architecture, vernacular dwellings as well as 19th and early-20th century commercial and public buildings. The district contains approximately 270 structures of which nearly 90 percent are contributing to the character of the district.Among the contributing structures are: Beckford Avenue Tenant Houses (c.1870) Boxwood Gardens (c.1850) Charles Jones House (c.1780) Colonel George Handy House (1805–06) John W. Crisfield House ("Somerset House") (c.1852 and earlier) Linden Hill (c.1750, c.1835) Littleton Long House (c.1830) (See Somerset County Historical Trust) Nutter's Purchase (c.1800) St. Andrews Episcopal Church (1767–73, 1859, 1896) Teackle Gatehouse (c.1805) Washington Hotel (c.1797, 1838) William Geddes House ("Tunstall Cottage") (c.1755) William W. Johnston House (c.1834-35) Woolford-Elzey House (c.1788, c.1840)It was listed on the National Register of Historic Places in 1980.

The Teackle Mansion is a historic estate at 11736 Mansion Street, Princess Anne, Maryland, United States. It was constructed between 1802 and 1819 for Littleton Dennis Teackle and his wife Elizabeth Upshur Teackle. It is notable for its Neoclassical architecture with many distinctive features, and its 19th century period rooms. It is the home of the Somerset County Historical Society, and was added to the National Register of Historic Places in 1971.It is mentioned in the novel The Entailed Hat by George Alfred Townsend.

Beckford is a historic home located at Princess Anne, Somerset County, Maryland, United States. It is a late Georgian Flemish bond brick dwelling, five bays wide by three bays deep, two stories with a hipped roof and two large interior chimney stacks. It is situated on the crest of the slope rising from the eastern bank of the Manokin River.Beckford was listed on the National Register of Historic Places in 1974.

Hytche Athletic Center is a 5,500-seat multi-purpose arena in Princess Anne, Maryland. It is home to the University of Maryland Eastern Shore Hawks men's and women's basketball teams and women's volleyball team. It replaced J. Millard Tawes Gymnasium as the home of UMES basketball upon its opening in 2000.

University of Maryland Eastern Shore (UMES) is a public historically black land-grant research university in Princess Anne, Maryland. It is part of the University System of Maryland. It is classified among "R2: Doctoral Universities – High research activity". It was established as Delaware Conference Academy. It has also been known as Princess Anne Academy and other names during its evolution.

Hawk Stadium is a baseball venue in Princess Anne, Maryland, United States. It is home to the Maryland Eastern Shore Hawks baseball team of the NCAA Division I Northeast Conference. The venue has a capacity of 1,000 spectators. It is located behind the Hytche Athletic Center, the home of UMES basketball.The stadium has been renovated twice. In 2008, the field was resodded, new wind screens and foul poles were added, and the dugouts and press box were repainted. In 2018 and 2019, sod was replaced, the outfield wall was rebuilt, and a new scoreboard was installed while the Hawks played both seasons at Arthur W. Perdue Stadium in Salisbury, Maryland. The Hawks 2020 season was also scheduled at Perdue Stadium "while renovations continue[d] at their on-campus facility." No 2021 season was played due to the COVID-19 pandemic. The Hawks 2022 season was also played at Perdue Stadium.

The Glebe House, also known as Davis's Choice, Turner's Purchase, and incorrectly as the Samuel Chase House, is a historic house at 10950 Market Lane in Princess Anne, Maryland. The 1+1⁄2-story house was built in 1784 and is a rare instance of an 18th-century brick-ender, a building form that was once common on the Eastern Shore of Maryland. The house has three wood-frame walls, and the fourth is of brick laid in Flemish bond with a projecting water table. The house was substantially altered in the 1920s when its roof was raised and a second story was added, but this work was undone when the house underwent restoration around the turn of the 21st century. It was long thought to be of greater age, and the childhood home or birthplace of Samuel Chase, a signer of the United States Declaration of Independence, but documentary research has shown these connections to be incorrect.The house was listed on the National Register of Historic Places in 2009.

The Catalpa Farm is a historic home and farm complex located at Princess Anne, Somerset County, Maryland, United States. It is a two-story, five-bay center passage structure built in two principal stages. The older section is a two-story, three-bay side-hall parlor house with service wing erected around 1825–1840. A two-story one-room plan frame addition was attached shortly thereafter. Also on the property are an early 19th-century dairy and smokehouse, a late 19th-century privy, a modern garage, a mid-19th-century corn crib, an early 20th-century gambrel-roofed barn, and an early 19th-century tobacco house.The Catalpa Farm was listed on the National Register of Historic Places in 1988.

The Waddy House, also known as the Williamson farm or the Jarvis Ballard house, is a historic home located at Princess Anne, Somerset County, Maryland, United States. It is a 1+1⁄2-story, Georgian-style mid-18th-century brick house supported by a raised Flemish bond brick foundation. The four-room plan dwelling measures 32 feet across by 32 feet deep. The house is one of a small collection of early brick houses surviving in Somerset County.The Waddy House was listed on the National Register of Historic Places in 1988.