Digges-Sasscer house

Upper Marlboro, officially the Town of Upper Marlboro, is the seat of Prince George's County, Maryland. As of the 2020 census, the population within the town limits was 652, although Greater Upper Marlboro, which covers a large area outside the town limits, is many times larger.

The Upper Marlboro Residential Historic District is a national historic district encompassing a historic residential area of Upper Marlboro, Maryland. The area reflects the town's growth from the 18th to the 20th century, including its importance as the county seat of Prince George's County. The district also contained a significant post-American Civil War African-American population, which was making the transition from slavery to freedom. Located in the district are three previously listed properties: Kingston, Content, and the John H. Traband House. Prominent features of the district include the Trinity Episcopal Church at 14519 Church Street, an 1846 Gothic Revival church designed by Robert Carey Long, Jr., and 5415 Old Crain Highway, a 1+1⁄2-story wood-frame house dated to c. 1730, which is believed to be the oldest building in the town.The district was listed on the National Register of Historic Places in 2012.

Content, also known as the Bowling House, is a historic home located in Upper Marlboro, Prince George's County, Maryland, United States, across the street from the county courthouse. The home is a 2+1⁄2-story, two-part frame structure built in three stages. The first section, built in 1787, consisted of the present main block, with a stair hall and porch added ca. 1800. A north wing was added before 1844. Content is one of the oldest buildings remaining in the county seat of Upper Marlboro, along with Kingston and the Buck (James Waldrop) House. Content has always been owned by prominent families in the civic, economic, and social affairs of town, county, and state including the Magruder, Beanes, and Lee families; and the Bowling and Smith families of the 20th century.Content was listed on the National Register of Historic Places in 1978. It is located in the Upper Marlboro Residential Historic District.

Kingston, or Sasscer's House, is a 1+1⁄2-story historic home located at Upper Marlboro, Prince George's County, Maryland, United States. It is believed to be the oldest building remaining in the town of Upper Marlboro and may have been built, at least in part, before 1730. Many alterations and additions were made to it in the Victorian era, including "gingerbread" details typical of this era. The Craufurd family cemetery is located in the woods northwest of the house.Kingston was listed on the National Register of Historic Places in 1978. It is located in the Upper Marlboro Residential Historic District.

The Olde Towne Inn (“O.T.I”) is a restaurant located in Upper Marlboro, Maryland, USA, previously known as the Judges Chambers. Since 2006 the restaurant has been owned by chef and restaurateur, Donnell Long, an African American and Washington, DC native.

Prince George's County Public Schools (PGCPS) is a public school district that serves Prince George's County, Maryland. During the 2023-2024 academic year, the district enrolls around 133,000 students and operates over 200 schools. PGCPS is the second-largest school district in Maryland, the third-largest district in the Washington-Baltimore metropolitan area, the 18th-largest in the United States, and the nation's largest school district with a majority-black student population. Headquartered in Upper Marlboro, PGCPS is the county's sole school district. The Prince George's County Board of Education (BoE) comprises 14 members who oversee the Superintendent.The current Superintendent is Millard House II.

Darnall's Chance, also known as Buck House, Buck-Wardrop House, or James Wardrop House, is a historic home located at 14800 Governor Oden Bowie Drive, in Upper Marlboro, Prince George's County, Maryland, United States. It is named after Colonel Henry Darnall, a wealthy Roman Catholic planter, who was the Proprietary Agent of Charles Calvert, 3rd Baron Baltimore and who served for a time as Deputy Governor of the Province. The house itself was built c. 1742 by a merchant named James Wardrop who bought some of Darnall's land from Eleanor Darnall Carroll and her husband Daniel Carroll, a politician and wealthy planter. Wardrop enslaved 32 people at the house.Today, Darnall's Chance houses the Darnall's Chance House Museum, a historic house museum which opened to the public in 1988.

The John H. Traband House is a historic home located at Upper Marlboro in Prince George's County, Maryland, United States. It was built between 1895 and 1897, and is a 2+1⁄2-story, asymmetrically shaped Queen Anne influenced frame structure of modest size and detailing. Also located on the property are a frame two-story gable-roofed carriage house. The house was constructed as the residence of a prominent citizen, John H. Traband (1857–1938), who was a successful businessman and landholder in Upper Marlboro.The John H. Traband House was listed on the National Register of Historic Places in 1984. It is located in the Upper Marlboro Residential Historic District.

Frederick Sasscer High School, also known as Frederick Sasscer Junior/Senior High School (FSHS), was a mid-20th century secondary school located at 14201 School Lane, Upper Marlboro, Prince George's County, Maryland, United States of America. FSHS's historical importance and its character lie in its centuries-old roots in the Town of Upper Marlboro, Maryland.

St. Mary's Beneficial Society Hall, constructed in 1892, is a historic building located in Upper Marlboro, Prince George's County, Maryland. The Hall, an excellent example of an African American multi-purpose building, served as a meeting place, social and political center, and house of worship for African Americans living in a segregated society. It is located nearly across the street from St. Mary's Catholic Church, with which it is historically associated. It is a one-story wood frame gable-front building, In 1988, a law firm acquired the building and converted it to office space.It was listed on the National Register of Historic Places in 2005.

The Show Place Arena is a 5,800-seat multi-purpose arena just south of Upper Marlboro, Maryland, which is used for sporting events, concerts, boxing and professional wrestling events, consumer shows, trade shows, religious services, graduations and other events. Opening in 1993, the Show Place Arena contains a 35,360-square-foot (136' by 260') floor allowing it to be used for various events such as concerts and trade shows. There are telescopic bleachers which can be placed in an open position to allow more permanent seating for events. In addition, equestrian, rodeo and other events use the arena with 6-8 inches of stonedust on the concrete floor to provide the preferred footing for equestrian events. The arena is currently home to horse shows, computer shows, train shows, concerts, religious events, cultural festivals, trade shows and graduations. The facility was also the venue for the 2004–2005 season of the American Basketball Association Maryland Nighthawks as well as home of the Patriot League Men's and Women's Basketball Championship in 2002-2004, the Chesapeake Icebreakers minor league hockey team (1997–1999), the Chesapeake Tide and Maryland Maniacs indoor football teams and the 2010 Atlantic 10 Conference Women's Basketball Tournament. It had served as the host of the Colonial Athletic Association Women's Basketball Tournament from 2011 to 2016. The arena has two Daktronics message/scoreboards and the floor to ceiling height measures 40 feet. There are three spotlights in the arena and a portable stage. The arena also contains two backstage ramps and two permanent concession stands plus a full-service bar. The arena also features ten handicapped-accessible restrooms and five private suites. There are three meeting rooms measuring a total of 7,000 square feet (700 m2). Seating capacities are 3,000 for rodeos and horse shows, 5,500 for hockey and basketball, 5,200 for boxing and wrestling and up to 4,700 for concerts. A clock tower is located near the main entrance. There are 2,500 parking spaces at the complex with another 3,000 within walking distance. In 2014, the building received significant upgrades to both the building and equipment used for hosting equestrian events.In October 2022, it hosted the Washington International Horse Show. It was the first time in more than 20 years the WIHS was hosted in Prince George's County.

Greater Upper Marlboro is an area of Prince George's County, Maryland that completely surrounds Upper Marlboro, the county seat. It was formerly a census-designated place (CDP), with a population of 18,720 at the 2000 census. However, the 2010 census divided the area into several smaller CDPs, including portions of Marlboro Meadows, Brock Hall, Marlboro Village, Queenland, and Croom.