Wellington Wildlife Management Area

Burton Cannon House, also known as Windsor, is a historic home located at Cokesbury, Somerset County, Maryland. It is a 1+1⁄2-story frame dwelling, four bays wide and two bays deep.. It was built in the late 1790s.It was listed on the National Register of Historic Places in 1975.

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.

Cokesbury is an unincorporated community in Somerset County, Maryland, United States. It is located east of U.S. Route 13 near the Pocomoke River, at the intersection of Wallace Taylor Road, Cokesbury Road, and Courthouse Hill Road. Burton Cannon House was listed on the National Register of Historic Places in 1975.

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.

Beverly is a historic home located at Princess Anne, Somerset County, Maryland, United States. It is a 2+1⁄2-story, Federal-style, Flemish bond brick dwelling measuring 40 feet by 60 feet. It was built by Nehemiah King II between 1785 and 1796. The interior of the house was partially destroyed by fire in 1937 but was restored from plans.The house was listed on the National Register of Historic Places in 1973.

Hayward's Lott, also known as Ivy Hall, is a historic home located at Pocomoke City, Somerset County, Maryland, United States. It is a 2+1⁄2-story farmhouse built about 1730 of Flemish bond brickwork with glazed headers. The house features small windows in the principal elevations, a steeply pitched roof, and two interior T-shaped chimneys.Hayward's Lott was listed on the National Register of Historic Places in 1976.

West Pocomoke is a census-designated place (CDP) in Somerset County, Maryland, United States. The population was 498 at the 2000 census. It is included in the Salisbury, Maryland-Delaware Metropolitan Statistical Area.

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.

Puncheon Mill House, also known as Puncheon's Landing, is a historic home located at Pocomoke City, Somerset County, Maryland. It is a two-story, three-by-two-bay gable-front frame dwelling supported on a raised common bond brick foundation. It was built between 1810 and 1820, and is sheathed with beaded cypress weatherboards and covered with a medium-pitched wood shingle roof. The house was restored and expanded in the 1960s with the addition of a kitchen wing.It was listed on the National Register of Historic Places in 1994.

The Eastern Correctional Institution (ECI) is a medium-security state prison for men located in Westover, Somerset County, Maryland, owned and operated by the Maryland Department of Public Safety and Correctional Services. Eastern has a minimum-security Annex, completed in 1993, and housing some 560 inmates. The total capacity of the minimum- and medium-security sections is around 3,400. With an actual population of about 3,300, this is Maryland's largest prison.The facility is adjacent to the Somerset County Detention Center. In October 2016, federal authorities indicted eighty people as part of a scheme to smuggle drugs, telephones and pornography into the facility. Also while there the federal authorities investigated 6 different murders within the facility one of them resulting in one inmate being partially decapitated. The investigation led to the charge and conviction of an inmate Patrick Simpson#3378314 who was also under suspicion for 2 previous murders and for smuggling large amounts of illicit drugs and tobacco. Simpson subsequently pleaded out to assault with a deadly weapon and received an additional 2 years on his sentence to be served before his release.

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.